Wikipedia talk:WikiProject Chemicals/Archive 2008

Archived discussion of WT:Chem in 2008

Diesel/Petroleum fuels

I'm not an active Chemistry project member but was wondering if any of the following articles are within the scope of your project (if not, where else they could/should be): Diesel, Biodiesel, Liquefied petroleum gas, Ethanol fuel. SheffGruff (talk) 18:36, 20 December 2007 (UTC)

• They're correctly attributed to the Energy wikiproject. I added the {{chemistry}} with ratings to Diesel and LPG. Wim van Dorst (talk) 01:05, 8 January 2008 (UTC).

Lead(II) nitrate, back to FA?

Hi, all, I've copy-edited the lead(II) nitrate article from the Chemicals wikiproject, after it was recentely demoted from its FA-status. Would interested WP:Chem editors please be so kind as to provide feedback in its now running FA re-candidacy? Wim van Dorst (talk) 19:18, 31 December 2007 (UTC).

• The FAC process for lead(II) nitrate has progressed well, with supporting starting to outbalance opposition. Please be invited to cast your votes now too, preferably positive, of course. Wim van Dorst (talk) 22:13, 14 January 2008 (UTC).
  • Yeah! Done. Wim van Dorst (talk) 21:07, 22 January 2008 (UTC).

Multiple symbols for a single unit

As part of the discussion of the possible FA status of the lead(II) nitrate article, the question of the 'correct' symbol for the litre came up. According to SI policy, both 'L' and 'l' (and thus mL and ml, etc) are accepted, and both are used on wikipedia. As I understand it, the 'l' usage is common in Europe, whilst Australia, Canada, the US, and others favour 'L'. I am wondering whether some consensus usage would be helpful. I don't think we need different usages on different pages - or worse, on a single page. Thoughts? EdChem (talk) 13:54, 7 January 2008 (UTC)

• I vote for upper case "L" simply because it is distinguishable from the numeral "1" when a sans-serif font is used. That said, I don't think we should go on a witchhunt to find and replace all instances of one with the other because there are really, better things to do on wikipedia. Either ml or mL should be consistent within the page, and that is enough. Similar arguments for the variant of English used. --Rifleman 82 (talk) 14:32, 7 January 2008 (UTC)
• I agree with R on mL, purely on font considerations. Consistency within an article is the important issue. Axiosaurus (talk) 15:18, 7 January 2008 (UTC)

• Totally disagree: in the old world Europe, it has always been lowercase 'l'. The uppercase 'L' alternative is only SI-allowed for some years, and definitely should not be the only designating symbol for 'litre'. If anything, we should formally denounce the use of either in our articles and use m³ (with formal SI-standard prefixes where appropriate). That should them be part of the Wikipedia:WikiProject Chemicals/Style guidelines. And I do agree with EdChem on the consistent use on a single page, whichever the choice. Wim van Dorst (talk) 01:01, 8 January 2008 (UTC).
  • I disagree with Wim because I believe Wikipedia is descriptive, not prescriptive. The truth is that liters and variants are commonly used by chemists, and we should not ban the use these units on philosophical grounds. --Rifleman 82 (talk) 03:12, 8 January 2008 (UTC)
• I agree with Rifleman also. The capital one has been a formally accepted alternative by SI since 1979. And I disagree with m³ and related "cubic-length volume" units (unless one is emphasizing the unit equivalence as part of some math, obviously). I think it makes an already technical realm of WP too technical for no real gain in understanding. In a practical sense, volume-measuring devices are usually marked in direct volume units, no reason to obfuscate the issue for lay audiences, and someone who cares about precise cubic-length terminology already knows enough to convert it. DMacks (talk) —Preceding comment was added at 05:56, 8 January 2008 (UTC)

So, what is now the conclusion? It is clear that we will not prescribe the use of only m³ and dm³. But do I understand that we will allow consistent use within one article of (US spelling) the 'L' for liter, and (GB spelling) the 'l' or the 'L' for litre? Anyone going to write that up in the styleguides? Wim van Dorst (talk) 19:51, 8 January 2008 (UTC).

I can remember having a vociferous argument with a French professor almost exactly 10 years ago on this very issue (Michel, if you're reading this, you know who you are!). The litre is defined as one cubic decimetre: it has two possible symbols, l or L International Bureau of Weights and Measures (2006), The International System of Units (SI) (PDF) (8th ed.), p. 124, ISBN 92-822-2213-6, archived (PDF) from the original on 2021-06-04, retrieved 2021-12-16. I agree that we should be consistent within a given article, but I don't see what authority we have to impose one over the other (or to impose the dm³
over either of them). Physchim62 (talk) 20:30, 9 January 2008 (UTC)

• Like this? Wim van Dorst (talk) 23:14, 9 January 2008 (UTC).

What is the ACS Style Guide recommendation here, and what about similar style guides from other such organizations? Since we're making a (somewhat) arbitrary (though rationalizeable) style-guide decision here, would be useful to consider what other such guides suggest. DMacks (talk) 23:39, 9 January 2008 (UTC)

Good news - fact checking of chemboxes, etc

User:ChemSpiderMan (aka Antony Williams) has very kindly taken on an absolutely mammoth task - he is checking every single chemical substance chembox for accuracy. Although he is remarkably fast at this, it still involves MANUALLY checking every IUPAC name and structure, as well as generating an InChI and InChiKey for each one. Last I heard he'd spent over 36 hours of hard slog on this! His plan is then to link to Wikipedia from each relevant substance entry on his ChemSpider website. Obviously this is great news for us all round, but there are a couple of things we will need to do:

1. Take a look at his PDF file listing possible problems, and leave comments here. Some refer to drugboxes - I have contacted the Pharmacology folks who write those. I have limited time right now, so I certainly can't fix them all myself, though I'll try to get to some ASAP. Some require us to reach a consensus. If anyone has time to help me work on these, please do, and post comments at User:Walkerma/Sandbox.
2. We need to decide how to use this file and all the information contained in it. Should we get a bot to read the file and add in the InChIs and InChIKeys into all of the articles? If so, we need to decide if the InChIKey should be placed in the chembox or hidden as with the InChI (NB: I think InChIKeys are limited to 26 characters)
3. There is a wider interest in the chemistry community for using Wikipedia chemistry pages, especially the chemical substance pages, to provide data for databases. See this recent talk page entry and this blog entry.

I'd like us to hold an IRC meeting next week to discuss some of this - would this be OK? Please comment below if you have any thoughts. Walkerma (talk) 04:01, 8 January 2008 (UTC)

That's great. Would be happy to help. IRC is fine. I'm available most weeknights 9-12 my time (1700-2000 GMT). --Rifleman 82 (talk) 04:32, 8 January 2008 (UTC)

ChemSpiderMan says: It's actually well over 120 hours of work so far. I estimate the total work will be around 300 hours, maybe more. The second PDF file is simply an update to the first file so you can junk the first PDF file. I actually made some edits on WP already from the initial list. Some of the edits are names but there are also incorrect structures as will become evident. The latest PDF file is on the ChemSpider site for anyone to read. I will keep updating on an ongoing basis. I'm up for attending an IRC discussion on this - I am just over 1/2 way through the files I have about 3800 records left...not all will be structures..there is no way to check except to open the record link.

What I'd like to discuss at the end of my project is a second level of curation. My intention is to produce an SDF file of structures and make it available to the WP:CHEM team for them to use. I am considering making the data freely available to everyone...a Wikipedia Structure file and it will therefore be possible to make Wikipedia structure and substructure searchable using other software tools. --ChemSpiderMan (talk) 05:00, 8 January 2008 (UTC)

The work that you are doing, Antony, is greatly appreciated. I've noted most of your comments and fixed many of the problems you have identified on article talk pages. If there are inconsistencies that have still not been addressed, feel free to note them here and someone will look into it, or let me know on my talk page and I'll do whatever I can to help fix it.

I really like the idea of a Wikipedia chemical structure file that would be substructure searchable. -- Ed (Edgar181) 23:03, 8 January 2008 (UTC)

Update of Wikipedia Review File I have updated the review file tonight and would welcome any feedback. Walkerma, you might want to upgrade your comments page with the new structures Details are available online here --ChemSpiderMan (talk) 12:40, 9 January 2008 (UTC) New update of project file available as of 1/15/2008 here --ChemSpiderMan (talk) 14:53, 15 January 2008 (UTC)

Dihydrogen hexachloroplatinic(IV) acid... or is it chloroplatinic acid?

Did a bit of copyediting here. I'll re-do the images eventually, but if someone else beats me to it... Question about the article name. Which should we use? I see the "chloroplatinic acid" more often. Any comments? Whatever we choose as the preferred, someone (I can) will have to edit the article to be consistent. Lastly, does anyone have easy access to this article?

R. T. Moravek, G. B. Kauffman and T. Mahmood (1967). "Nitrosyl Hexachloroplatinate(IV)". Inorganic Syntheses. 9: 217–220. doi:10.1002/9780470132555.ch63.

If this impurity is due to the action of the aqua regia, perhaps the section on "related compounds" can be rewritten into "production". --Rifleman 82 (talk) 16:33, 9 January 2008 (UTC)

It is certainly not "Dihydrogen hexachloroplatinic(IV) acid"! Hexachloroplatinic acid if you must. Physchim62 (talk) 20:09, 9 January 2008 (UTC)

Assuming you are going to end up with (H+)2 PtCl6-- then I believe the name should be Dihydrogen hexachloroplatinate(2-). I have confirmed this name in the naming software I have access to. --ChemSpiderMan (talk) 04:37, 10 January 2008 (UTC)

The renaming of sulfuric acid to dihydrogen sulfate might give a clue which name is the right one!--Stone (talk) 12:50, 10 January 2008 (UTC)

Hexachloroplatinic acid is the appropriate name for H₂PtCl₆. The PtCl₆²⁻ ion would be called the hexachloroplatinate(IV) anion - the parentheses show the metal oxidation state rather than the overall charge (hence IV, not II-), and the "-ate" suffix indicates an anionic species. In the unlikely event that the anion HPtCl₆⁻ could be prepared, it would be named the hydrogenhexachloroplatinate(IV) anion. The name dihydrogen hexachloroplatinate(IV) would be used only if the pure substance were obtained as a molecular species or an ionic solid; when any such substance were dissolved in water and it dissociated or ionised, it should be referred to as hexachloroplatinic acid. The situation is similar to that for HCl - hydrogen chloride as an unionised molecule (usually as a gas), hydrochloric acid as an ionised aqueous solution. As for the chloroplatinic acid name, it may be used, but it is imprecise in my opinion, as it could be taken to refer to H₂PtCl₄. EdChem (talk) 14:22, 10 January 2008 (UTC)

Hexachloroplatinate(2-) is a perfectly correct name for the anion: note the difference in usage between Arabic and Roman numerals. The anion usually known as superoxide could also be referred to as dioxide(1–): it is impossible to assign an oxidation state to each of the oxygens. For the case in question, my preference is for hexachloroplatinic acid, which is unambiguous and easily recognised. Physchim62 (talk) 16:38, 10 January 2008 (UTC)

IRC discussion on using Wikipedia chemistry pages to provide chemical data

I'm proposing that we hold an IRC discussion this coming Tuesday. As you may have gleaned from recent postings, there is interest in using the Wikipedia chemical information, particularly information from Chemboxes, as the starting point for open access databases.

Background

• ChemSpider
• Cambridge University
• this post from Cambridge.
• You may want to brush up on terms such as RDF, CML, SDF file.

How it may affect us

• Curation (fact-checking) of data forcing us to clean up faulty or dubious data
• Mashups with other websites, these could bring chemists from other sites onto Wikipedia
• We may need to write a bot or reformat our data in order to make Wikipedia chemistry more accessible for the semantic web

Time

Tuesday, January 15th at 1900h 1600h UTC (11am US Eastern Time, 1700h Central European Time). Please note earlier time.

Location

Wikipedia chemistry IRC channel

Possible agenda items

• What do we have? The dataset of chemical compounds, currently being cleaned up by ChemSpiderMan et al. - numbers, quality? Data in other chemistry articles, e.g. on chemists?
• How can we make the data more easily searchable/mineable, and more suitable for the semantic web?
• How can we foster mashups with other sites that might bring chemists to us, while providing useful chemical information for the other site?

Attendance

If you think you can attend, please sign up below. If you're not familiar with IRC, see this page and download simple software such as Chatzilla (for Firefox). User:Walkerma manages to use it, so it MUST be simple....!

• I can make either time. Walkerma (talk) 20:18, 12 January 2008 (UTC)
• I'll try. --Dirk Beetstra ^{T C} 20:50, 12 January 2008 (UTC)
• I'm in. DMacks (talk) 22:03, 12 January 2008 (UTC)
• I can attend. Also, in preparation for the meeting people might want to see the latest report that I have put online tonight here--ChemSpiderMan (talk) 01:22, 13 January 2008 (UTC)
• I can attend at 1600 UTC, but probably not at 1900. --Itub (talk) 09:25, 13 January 2008 (UTC)
• I will try to attend--Rzepa (talk) 14:00, 14 January 2008 (UTC)
• I'll try. --Arcadian (talk) 06:27, 15 January 2008 (UTC)

Comment

Can we have it a bit earlier? By three hours — 1600 GMT/1100 Eastern US/1700 Central European/2400 Singapore? --Rifleman 82 (talk) 01:50, 13 January 2008 (UTC)

• sigh*, I guess I could get up before noon on a vacation day if others prefer this time. DMacks (talk) 01:58, 13 January 2008 (UTC)

Oh dear! It's hard to fit everyone in, and I thought we'd covered everybody. I'm reluctant to switch things right now, just because I've been emailing people trying to find a convenient time, but I'll look into it. Are there any Californians, etc, who plan to attend? Walkerma (talk) 04:55, 13 January 2008 (UTC)

I must confess, that also fits better with me (19:00 is about dinner time for me .., late afternoon like 16:00 would indeed generally fit better), but I see that these meetings are problematic in time. --Dirk Beetstra ^{T C} 11:41, 13 January 2008 (UTC)

I am flexible in my availability but not between 2:30 and 5pm EST. I need to set up an IRC Client. Chatzilla is conflicting with FireFox and will not install. I am trying mIRC but have not been able to connect to the channel. I welcome assistance. At present I get a message that the channel is temporarily unavailable but it has been in this state for a while.--ChemSpiderMan (talk) 15:00, 13 January 2008 (UTC)

Give [1] a try? I get lots of problems with my uni blocking IRC, which causes a variety of messages (couldn't contact server, and with no server, channel unavailable). DMacks (talk) 15:58, 13 January 2008 (UTC)

It seems that everyone I've heard from, including Peter Murray-Rust, prefers the earlier time, so we'll go with that. Walkerma (talk) 20:43, 14 January 2008 (UTC)

Available bandwidth willing, I shall try to be there :) Physchim62 (talk) 13:11, 15 January 2008 (UTC)

AN updated PDF of the curation project report is available as of 1/15/2008. Available here--ChemSpiderMan (talk) 14:52, 15 January 2008 (UTC) Example of WP entry under CML/RDF for discussion on IRC Exploring RDF and CML [[2]] Petermr (talk) 16:10, 15 January 2008 (UTC)

Contribution for the Style Guidelines: layout of chemical reactions

Hi all, recent edits pointed out that there is a lack of layout definition in the WP:Chem Style Guidelines. Aspects that we ought to define include:

• wikilinking in formulae, used in-line and in reactions
• indentation of reactions
• use of (s)/(l)/(g) and ionic notiation

I think good:

H⁺(aq) + OH⁻(aq) → H₂O(l)

I think not good:

H⁺(aq) + OH^-(aq) → H₂O(l)

Please comment. Wim van Dorst (talk) 20:44, 13 January 2008 (UTC).

• My preference is for there not to be wikilinking in formulae or in equations - especially not when they are links like the O in OH⁻ linking to an article on the substance oxygen, as such links are potentially confusing. I don't object to links for states, as such links are simply explanations for the abbreviations used in equations.
• I believe that centring looks better than indenting for equations, but don't feel that strongly about which to use.
• Including states in equations is simply good practice. As such, we may also need to note the potential use of (sol) for cases where the solvent is anon-aqueous. Note, however, that equations in organic chemistry will frequently omit states, often including the solvent below the reaction arrow. On that subject, is there an easy way to do this? On the lead(II) nitrate page, I included an equation for the dissociation on dissolution, and would have preferred to have an 'H₂O' over the arrow, but don't know a convenient way of adding it.
• By 'ionic notation', I think Wim van Dorst is asking about net ionic equations as opposed to neutral species equations, and I strongly favour net ionic equations on the grounds of chemical accuracy.

EdChem (talk) 21:28, 13 January 2008 (UTC)

Re style guide:

• I oppose wikilinking atoms in formulae. Seems distracting, tedious, and pretentious, IMHO. When reading about lysergic acid, a reader does not seek a link to carbon. If the group decides that formulae should to be wikified, then I hope that we don't force this format onto every formula within an article.
• indentation of reactions. This style helps me with readability. On a printed page, centering is nice, but for some reason, I prefer the simple indent in WE.
• use of (s)/(l)/(g). Oppose strongly. My guess is that this notation comes from the days (about 50 centuries ago) when aqueous chemistry and qualitative analysis were emphasized. The style seems archaic. It requires knowledge that is often unavailable and implies restrictions that are usually irrelevant. Also, if I understand the convention, it implies a level of absolutism that is misleading, i.e. that PbCl2 is insoluble, whereas it is poorly soluble in water. And it implies that most chemistry is aqueous, which is untrue for large parts of the field. Yes, in the 1950's it was comforting to see the precipitation of PbCl₂ indicated explicitly. We do not see this format in any modern journal or monograph. I also think that the style makes an already difficult topic (chemical reactions) more difficult because the reader must not only contend with the chemistry, but also the phases (which again are often not known or are misunderstood).
• ionic notation. Seems harmless often, but I prefer NaCl, not Na⁺Cl^-. The notation also seems archaic since it implicitly (to me at least) ignores ion-pairing.

It is healthy to have this discussion so that we can imput these recommendations into a style guide.--Smokefoot (talk) 22:42, 13 January 2008 (UTC)

I don't like wikilinking formulae either, especially as atoms. If some obscure compound were expressed in CHN formula, it might be justifible to wikilink the entire thing. See also discussion on mickey mouse structures. --Rifleman 82 (talk) 01:45, 14 January 2008 (UTC)

In formulating (!) my opinion, I tried to base my opinion on the likely reader of the article, and what area of chemistry is being discussed.

• I think wikilinking atoms in formulae is generally a bad idea (and very bad in something like lysergic acid), though I think it could be useful in a handful of basic articles such as water (molecule) or carbon dioxide, where the typical reader may be unfamiliar with what the formulae represent. It is somewhat helpful in an article like sodium chloride, because Na is not obviously sodium to a 12 year old, whereas MgCl₂ is perhaps easier to grasp. A more liberal option would be to link only from the lead paragraph, only in inorganic articles, where it says, "potassium phosphate has the formula...."; I could live with that. Wikilinking organic groups such as Ph is useful, because many beginning orgo students struggle with these, and they're not listed in the periodic table on the lab wall (while noting Physchim62's hatred of Me for methyl).
• Wikilinking a complete formula (once) in an equation IS appropriate (IMHO), particularly when the article is likely to be read by someone at the high school level. A more advanced reader probably won't even notice that Na₂SO₄ links to the sodium sulfate article, but that could be very helpful to a beginner.
• In aqueous reactions, particularly those involving gas evolution, precipitation, etc, including the state should be recommended, though not mandatory. Smokefoot is right for the research level, but millions of schoolkids around the world are still mixing silver nitrate with sodium chloride in water, and in articles like lead(II) nitrate they may find the little (s) helpful. It would look silly in an article like cobaltocene, though.
• I recommend a single indent (:) before text based equations, but structure-based (graphical) equations look better centred, IMHO.
• In an inorganic context, writing (say) sodium sulfate as Na₂SO₄ should be the norm, other than perhaps to point out (in a basic article) how it dissociates in water. However, there may be cases where the ionic representation is appropriate, for example in an organic context such as this. Obviously there are many occasions where net ionic equations etc are being used quite appropriately.

Walkerma (talk) 05:33, 14 January 2008 (UTC)

• I would favor: - no atoms links, no use of s,l,g (agree with smokefoot, old fashioned). Importantly I favor indentation over central positioning ALSO when it involves graphics. V8rik (talk) 16:39, 14 January 2008 (UTC)

• My preferences are: 1) indenting equations; 2) using ionic equations where the "neutral" equations would give the false impression that that the neutral "molecules" exist in solution (for example, using AgNO3 + KI -> AgI + KNO3 to describe an aqueous reaction); 3) not using s,l,g in general, although they can be used for emphasis in cases where phase transitions or precipitations are being discussed, or where necessary to define a thermochemical property clearly (for example, the enthalpy change from a combustion reaction is not the same if you end up with water vapor or with liquid water). 4) No wikilinks in formulas, although in a handful of basic articles they might be OK. I especially dislike "contiguous links" where different letters in a word or formula link to different articles, such as OH. Linking the whole formula to the relevant article might be OK in some cases, but it is probably better to give the name and link it instead of linking the formula. --Itub (talk) 17:34, 14 January 2008 (UTC)

To make a proposal for the Style Guidelines, how about (please copy-edit!):

---

Chemical reactions
Chemical reactions in articles should be properly balanced and correct. Formulae in the reactions should not be wikilinked (do that in the introductory text), nor should the atoms in the formulae be wikilinked. Reactions may be numbered for referencing in the text.

The use of phase indication (s), (l), (g) should only be used if emphasis on the phase transition in a reaction is intended. Generally, they should be avoided. If used, the first occurrence of the phase indication should be wikilinked.

Inorganic reactions and text reactions should be left-aligned, with one indent (wiki-markup ':'). Organic reactions are mostly presented in a graphical way, and treated as images, wrapping around text or centered.

The Bamberger rearrangement

Good examples:

H⁺(aq) + OH⁻(aq) → H₂O(l)

Na₂SO₄ + H₂SO₄ ⇌ 2 NaHSO₄

1. Dissolving pure iron in a solution of iron(III) chloride
   

Fe(s) + 2 FeCl₃(aq) → 3 FeCl₂(aq)

1. Dissolving iron ore in hydrochloric acid
   Fe₃O₄(s) + 8 HCl(aq) → FeCl₂(aq) + 2 FeCl₃(aq) + 4 H₂O
2. Upgrading the iron(II) chloride with chlorine
   2 FeCl₂(aq) + Cl₂(g) → 2 FeCl₃(aq)

Bad examples:

H⁺(aq) + OH^-(aq) → H₂O(l)

Na₂SO₄(aq) + H₂SO₄(aq) ⇌ 2 NaHSO₄(aq)

---

I generally agree with the comments above, as summarised by Itub. However, I would put in a word in favour of indications of phase in some cases. Details of phase abbreviations can be found at International Union of Pure and Applied Chemistry (1993). Quantities, Units and Symbols in Physical Chemistry, 2nd edition, Oxford: Blackwell Science. ISBN 0-632-03583-8. pp. 46–47. Electronic version. and at Cox, J. D. (1982). "Manual of Symbols and Terminology for Physicochemical Quantities and Units: Appendix IV—Notation for States and Processes, Siginificance of the Word "Standard" in Chemical Thermodynamics, and Remarks on Commonly Tabulated Forms of Thermodynamic Functions". Pure Appl. Chem. 54: 1239–50.

As Itub points out, it is often important to quote a phase when dealing with thermochemical quantities, eg

Cl
₂ (g) + 2e^–
⇌ 2Cl^–
(aq) ; E° = +1.3583 V

Cl
₂ (aq) + 2e^–
⇌ 2Cl^–
(aq) ; E° = +1.4203 V

(Student exercise: calculate the solubility of chlorine in water!)

They are also useful when discussing aqueous chemistry. In particular, I very much prefer H⁺
 (aq) to H
₃O⁺
: the former is correct and unambiguous, the latter is false in virtually every case in which it is used. Similarly, many students who write [[Fe(H
₂O)
₆]]³⁺
would not know what colour this ion actually is! (needless to say, they were not using it in their reactions, they were using a mixture of species which can be represented as Fe³⁺
 (aq)). The equation

Pb²⁺
(aq) + 2I^–
(aq) → PbI
₂ (s)

not only emphasises the precipitation of lead iodide but also the hydration (to an unknown degree) of Pb²⁺
and I^–
.

Finally, to reply to Martin, I have no objection to using "Me" for methyl in text formulae! I merely pointed out that we are being helpful to our German colleagues if we don't use it in graphic formulae: in return, they shouldn't use φ for phenyl :) (not that I ever seen that in graphics from dewiki). Physchim62 (talk) 14:16, 20 January 2008 (UTC)

I have some issues with the 'good examples' provided by Itub that have been written above, drawing on the potential for confusion when using neutral species equations instead of ionic equations, and when leaving out states. For example, the given equation

Na₂SO₄ + H₂SO₄ ⇌ 2 NaHSO₄

In an aqueous solution, I would suggest that a more appropriate equation would be:

SO₄²⁻(aq) + H⁺(aq) ⇌ HSO₄⁻

or maybe:

SO₄²⁻(aq) + H₃O⁺(aq) ⇌ HSO₄⁻ + H₂O(l)

or perhaps, if one were using conc. sulfuric acid:

SO₄²⁻(aq) + H₂SO₄(l) ⇌ 2 HSO₄⁻

but in such a case the equilibrium symbol is questionable, as the strength of sulfuric acid mandates a completion of this reaction. I am having trouble imagining a circumstance in which I might use the original equation as written. If the example was changed to something like sodium carbonate and citric acid (H₃cit, for convenience), then a neutral species equation would be appropriate if grinding solids together:

Na₂CO₃(s) + 2 H₃cit(s) → 2 NaH₂cit(s) + CO₂(g) + H₂O(l)

but in aqueous solution, I'd use something like:

CO₃²⁻(aq) + 2 H₃cit(aq) → 2 H₂cit⁻(aq) + CO₂(g) + H₂O(l)

Such equations require states to be meaningful, and I would argue that neutral species equations without states for simple general chemistry processes are appropriate only for stoichiometric calculations - and the omission of states is often necessary in such cases because no reasonable and meaningful set of states can be applied.

Another example was:

1. Dissolving pure iron in a solution of iron(III) chloride
   Fe(s) + 2 FeCl₃(aq) → 3 FeCl₂(aq)

where I would prefer a net ionic equation such as:

Fe(s) + 2 Fe³⁺(aq) → 3 Fe²⁺(aq)

Quite possibly E° = +1.21 V should also be appended, allowing the equation to illustrate why adding iron solid to an iron(II) solution will prevent the formation of substantial amounts of iron(III).

Adding spectator ions to equations can also introduce unneeded complexity. For example, suppose I were to add potassium permanganate solution, acidified with sulfuric acid, to a solution of iron(II) chloride. The net ionic equation allows the actual transformation to be seen clearly, emphasising the oxidation of iron(II):

5 Fe²⁺(aq) + MnO₄⁻(aq) + 8 H⁺(aq) → 5 Fe³⁺(aq) + Mn²⁺(aq) + 4 H₂O(l)

Now, to make a neutral species equation, I have to add 10 chloride ions, a potassium ion, and 4 sulfate ions. This immediately raises questions as to the other products. For example, which of the following options is 'correct'?

5 FeCl₂(aq) + KMnO₄(aq) + 4 H₂SO₄(aq) → 4 Fe(SO₄)Cl(aq) + FeCl₃(aq) + MnCl₂(aq) + KCl(aq) + 4 H₂O(l)

5 FeCl₂(aq) + KMnO₄(aq) + 4 H₂SO₄(aq) → Fe₂(SO₄)₃(aq) + 3 FeCl₃(aq) + MnSO₄(aq) + KCl(aq) + 4 H₂O(l)

5 FeCl₂(aq) + KMnO₄(aq) + 4 H₂SO₄(aq) → Fe(SO₄)Cl(aq) + 2 FeCl₃(aq) + Fe₂(SO₄)₃(aq) + MnCl₂(aq) + KCl(aq) + 4 H₂O(l)

10 FeCl₂(aq) + 2 KMnO₄(aq) + 8 H₂SO₄(aq) → Fe(SO₄)Cl(aq) + 5 FeCl₃(aq) + 2 Fe₂(SO₄)₃(aq) + 2 MnCl₂(aq) + K₂SO₄(aq) + 8 H₂O(l)

10 FeCl₂(aq) + 2 KMnO₄(aq) + 8 H₂SO₄(aq) → 6 FeCl₃(aq) + 2 Fe₂(SO₄)₃(aq) + MnCl₂(aq) + MnSO₄(aq) + K₂SO₄(aq) + 8 H₂O(l)

10 FeCl₂(aq) + 2 KMnO₄(aq) + 8 H₂SO₄(aq) → 2 Fe(SO₄)Cl(aq) + 6 FeCl₃(aq) + Fe₂(SO₄)₃(aq) + 2 MnSO₄(aq) + K₂SO₄(aq) + 8 H₂O(l)

I can argue for any of them, I suppose, but they are raising an issue that is chemically not relevant - since all of these soluble ionic products are dissociated in solution, trying to decide which spectator anions are 'paired' with which spectator cations is pointless.

Basically, states are needed because processes like:

Na₂CO₃(s) + 2 H⁺(aq) → 2 Na⁺(aq) + CO₂(g) + H₂O(l)

and:

CO₃²⁻(aq) + 2 H⁺(aq) → CO₂(g) + H₂O(l)

are different processes, and yet both could have the same neutral species equation:

Na₂CO₃ + 2 HCl → 2 NaCl + CO₂ + H₂O

and it is only this neutral species form that is appropriately stateless.

By the way, sorry for the length - I expected this to be shorter when I started typing! EdChem (talk) 11:03, 23 January 2008 (UTC)

Note: I didn't write those "good examples"! I think it was Wimvandorst. I'll comment on the specific points later. --Itub (talk) 11:54, 23 January 2008 (UTC)

Sorry, Itub, I appreciate your point. I am not looking to get into any criticism of people, and I have struck out your name. I am trying to comment on what might be included in general style guidelines, and am hoping that the use of appropriate net ionic equations (with states) be adopted for simple chemistry topics. EdChem (talk) 12:07, 23 January 2008 (UTC)

I once again oppose indicating states in the manner recommended by EdChem. We do not allow this format in journals, and few modern textbooks adopt it. This "fundamentalist" gesture would condemn WE-chem to appear old-fashioned or "mickey mouse," a trumping of the recommendations (above) by those that have considerable expertise on core content (vs format). We decided a long time ago that we were not going to demand "ethanoic acid," again despite the wailings of certain fundamentalists. I recommend that we drop this squabble about insisting (and resisting, in my case) states and get back to our main job: contributing excellent content. None of the monomethyl pyridines have their own pages!! We don't have a page on coordinative unsaturation! Readers are seeking overviews on biofuels, lignocellulose, and bioenergy.... There's more important work to do!--Smokefoot (talk) 15:01, 23 January 2008 (UTC)

I would like to let the editor decide which form of chemical reaction (s)he applies in a certain article, e.g., the dissolution of iron in a ferric chloride solution, as part of the production process of ferric chloride, is in my perception best shown as:

Fe(s) + 2 FeCl₃(aq) &rarr 3 FeCl₂(aq)

That is because a reader then can visualize the overall production process: a huge vessel filled with an dark brown watery solution, and bars of iron are dropped in it. And I seem to recall that iron does 'dissolve' much better in ferric chloride solution than in (e.g.) ferric nitrate or ferric sulfate.

As an alternative, if I would be describing the intricacies of the oxidation states of iron, I'd be using:

Fe⁰ + 2 Fe³⁺ → 3 Fe²⁺

And if the article would need to point out something like iron dissolution, one may use yet another reaction:

Fe(s) + 2 Fe³⁺(aq) → 3 Fe²⁺(aq)

So, the context defines the most appropriate reaction to be used. The styleguide now only shows (which ever reaction chosen) how to display it, viz., without wikilinking atoms or compounds, indented (not centred), etc. That's a nice step in the good direction for me. Up to the next FA: WP:Chem really needs a new one this year ;-). Wim van Dorst (talk) 21:26, 23 January 2008 (UTC).

{{Chembox new}}

I've done a final sweep using chem-awb (talk · contribs) of the remaining articles transcluding {{Chembox header}} but not {{Chembox new}}. There are 89 remaining which require substantial handcoding. See [3] Further discussion should be at Wikipedia talk:Chemical infobox. Help is appreciated! --Rifleman 82 (talk) 02:13, 14 January 2008 (UTC)

I have replaced the chem box on sulfate with chem box new. Originally I had removed it but this change was reverted. A brief scan of other ions/functional groups shows that using chem box in this way is unusual. However I can see why a summary box is useful. but using chem box seems to be overkill, and maybe confusing if later we link through it to other databases. Any thoughts? Axiosaurus (talk) 10:54, 19 January 2008 (UTC)

It is indeed unusual, I think I would remove the chembox there, though we could discuss having a specialised box for 'functional groups' .. --Dirk Beetstra ^{T C} 11:22, 19 January 2008 (UTC)

I was thinking of writing a style guide to functional groups, but I guess it's been pre-empted by this. I'm recovering from severe computer difficulties, but I will be able to get on it in by this weekend. I'll be counting on you guys for comments and feedback! --Rifleman 82 (talk) 12:47, 19 January 2008 (UTC)

• One can only assume you are already aware of Wikipedia:WikiProject Chemicals/Style guidelines? How would a 'functional groups' guideline differ? If complementary you might want to add to this? PS. Functional groups are a subject of wikipedia:WikiProject Chemistry. They are not chemicals, so they are not part of wikipedia:WikiProject Chemicals here. Wim van Dorst (talk) 19:43, 19 January 2008 (UTC).

• I would favour a new box- and yes I guess we should discuss this on the Chemistry page, but ensure we publicise any discussion here Axiosaurus (talk) 20:09, 19 January 2008 (UTC)

Linking CAS Numbers out from Chem and DrugBoxes

For those on the IRC Chat yesterday you will recall my concerns about linking out to other online services using CAS numbers to "search" databases. I believe it is a potentially daangerous practice. A single "compound/structure" can be associated with multiple CAS numbers. But a single CAS number should be associated with a single substance. So, having a CAS number associated with multiple compounds (neutral compound, chloride salt, bromide salt OR same connection table with multiple stereochemistries - absolute, partially defined, undefined) is not good in my mind. I might agree that linking the CAS number to ONE record in an external database, where that link is to the correct "structure representation" (i.e. that exact one given in the CAS registry) is correct. For sure we will not be doing these links INTO the CAS registry as we will not be given permission to do that gratis.

Example: 1) Fructose-1-phosphate: if you click on the CAS number you see THREE structures - only the second matches the structure shown in the ChemBox. This is not a direct link therefore ..it's a search. Now, additional structures might be added to the external site and associated with that CAS number by accident so the problem could get bigger. 2)Taxol. Presently ChemBox links out to MeSH. So, there are inconsistencies regarding WHERE CAS numbers link to. I would prefer MeSH if anywhere but there is actually little value at that page but it does lead you here. MeSH is HIGHLY curated, but not necessarily perfect. Using this CAS number as a search gives three hits in PubChem, seven hits in eMolecules and one hit on ChemSPider. Please note...this is NOT for any other reason other than the fact that the data for Taxol have been manually curated by me. There are MANY examples of multiple structures on ChemSPider with the same CAS number. The multiple Taxol structures are there because of differences in stereo.

I've opened the discussion...comments?--ChemSpiderMan (talk) 15:22, 16 January 2008 (UTC)

Please take into account here, that we are linking to eMolecules as a linkfarm to get more information, it is indeed a search. The other side of this medal could be the old situation, where there were sometimes extensive lists of external links in the external links section, providing links to several suppliers. That is something that certainly should be avoided.

I just found that also pubchem (for the above example of Fructose-1-phosphate) gives more than one result: pubchem (5 structures). Taxol contains a {{drugbox}}, so that links to another site, which is more 'drug-oriented', which explains the other link.

I have started a workshop on {{chembox new}} (first) to get a bit of line in certain aspects of the box. See Wikipedia:Chemical infobox/Workshop. Maybe that is a good place to have a discussion on 'what could link where' as well? Cheers. --Dirk Beetstra ^{T C} 16:55, 16 January 2008 (UTC)

Request to edit/provide feedback on ChemSpider article

As a result of ChemSpiderman (me) posting a link to an article regarding ChemSpider today EdJohnston approached me with a suggestion to update the article on Wikipedia. I have suggested some text but would prefer that someone else review/edit/comment/curate and post appropriate data representing the site rather than have it come from me. I welcome guidance and suggestions. My suggested text is here. In conversation with Ed today it turns out that there might be a perception that ChemSpider (because it is still a beta) is not a "working site". It presently has over 2000 people per day using the site for searching and has spiked at 3000. It is "labeled a beta" because I am not ready to name it as non-beta yet. It does not mean it's not used and does not mean it isn't providing value. It's been the basis of the majority of curation work I have done on Wikipedia which I do believe is of value. Comments welcomed.--ChemSpiderMan (talk) 22:41, 17 January 2008 (UTC)

Weekly IRC meetings for WP:CHEMISTRY/WP:CHEM

We had an IRC meeting on Jan 15, 2008 to discuss validation of chembox information and reuse of the data in databases and mashups. We agreed to meet again informally one week later (today, Jan 22) to discuss some of the details, like how to structure the data, how to deal with salts, etc. It looks like this will become a regular meeting, so we have set up a page at Wikipedia:WikiProject_Chemistry/IRC_discussions. Please join us on January 29 at 1600h UTC (11am US EST, 1700h Central European Time)! We hope to discuss InChIs and InChIKeys, though it will depend somewhat on who is able to come to the meeting. Cheers, Walkerma (talk) 18:41, 22 January 2008 (UTC)

Validation of CAS numbers in chemboxes - please help

ChemSpiderMan has recently been doing validation work on our chembox data, but he can't do CAS nos. For this reason we will be doing this ourselves over the coming weeks/months, so please try and help out if you can. We could presumably also be adding CAS nos. for those pages that lack them. The work page for this is at Wikipedia:WikiProject Chemistry/CAS validation.

Some questions:

1. Is there some way for us to integrate the resultant information into the pre-existing page, List of CAS numbers by chemical compound?
2. Should we create redirects for CAS nos. - where those don't currently exist - or should we rely on the search capability to find the article from a CAS# search?
3. This list is only organics, at some point we'll have to be looking at inorganics as well.
4. Can anyone draft a student in to help?

I'm guessing that a bot or AWB could do the first two tasks fairly easily, though I don't know. Walkerma (talk) 20:44, 22 January 2008 (UTC)

I could easily write a script to do the first one, does not need a bot-account (I can copy-paste the result in the end). Generating the second is more difficult, I would need a bot-account for that, I can see if User:Rifleman_82 can run perl-scripts (he should be able to on his linux-box). I guess I would pull the information from the transclusions of {{chembox new}}, which would result in a full list, including inorganics. --Dirk Beetstra ^{T C} 21:55, 22 January 2008 (UTC)

I have no problem going back through inorganics in the future but note that my project intention is to make Wikipedia structure/substructure searchable and in many cases the inorganics don't have structures. Rather, they have formulae. Let me finish the "organics" first...it's a big enough project...then we discuss what has been learned by this project and go after inorganics and organometallics.--ChemSpiderMan (talk) 03:28, 23 January 2008 (UTC)

Please also note that many compounds have multiple CAS numbers. Especially amines and organic acids have different CAS numbers for all their salts. It might be a good idea to list all of them. Сасусlе 04:44, 23 January 2008 (UTC)

This was part of the IRC Chat today...my belief is that the ChemBox should be "self-consistent". The structure, IUPAC name, CAS number, SMILES should all refer to the same structure. IF there is a decision to list all CAS numbers then they need to be annotated..for example (chloride salt, bromide salt etc). Personally I think this should either be an additional component of the ChemBox or not present at all. The ChemBox should be preserved to describe the chemical/substance being displayed/discussed and not represent multiple compounds. --ChemSpiderMan (talk) 05:12, 23 January 2008 (UTC)

I am working through the chembox new list and sorting the inorganics. The problem ones, and there aren't that many, have the same issues --e.g. (i) multiple compound "versions" described in the chembox typically hydrates; (ii) some compounds e.g.gold(IV) bromide that have 2 CAS numbers etc etc. I will be interested to see what comes out of the organics push. Definitely the area to focus on, after all Wiki is short of content on organometallics and transition metal complexes and clusters. Its not even hot on basic inorganic! --Axiosaurus (talk) 19:22, 24 January 2008 (UTC)

Axiosaurus..you might be aware of the validation exercise I have undertaken on chemical "structures" on Wikipedia? I am willing to take on the same on inorganics but am more interested in doing organometallics next in reality. I would like to support both on ChemSpider...and do to a certain extent...but would want to work with someone on Wikipedia to clarify inorganic and organometallic structures. I assume you might be interested. if so, please initiate a conversation on my Talk Page. Thanks--ChemSpiderMan (talk) 20:27, 24 January 2008 (UTC)

New articles

Phenidone, Uragan D2, α-Santalol, 2-Heptanone and Imidazolidinyl urea every one might have a look.--Stone (talk) 08:45, 24 January 2008 (UTC)

Stone..I've checked the ChemBoxes when available. The Imidazolinyl Urea article was a problem. Check the history and you will see what I tried to do with the Name...the best name is with the N',N italicized but, try as I might, I cannot get this into the box: N',N-methylenebis{1-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea}. Maybe there is a trick I am yet to learn for this. Can you insert the IUPAC Name above into the box?--ChemSpiderMan (talk) 13:33, 24 January 2008 (UTC)

I just noticed theat Media-wiki is interpreting the primes...it should be N-prime, N-triple prime —Preceding unsigned comment added by ChemSpiderMan (talk • contribs) 13:35, 24 January 2008 (UTC)

I replaced the characters by unicode prime characters, which are different from the normal "single quote" characters. For the triple prime I used three prime characters; there is also a "triple prime" character but it doesn't look to good on my computer... --Itub (talk) 13:43, 24 January 2008 (UTC)

Another option if you want to use normal quotes is to use <nowiki>''</nowiki>. --Itub (talk) 13:45, 24 January 2008 (UTC)

Another new article, I just started DMPU (1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone), shoot it if you want. --Dirk Beetstra ^{T C} 11:57, 25 January 2008 (UTC)

Comments added to the article. I have already added the structure into the curation set I am working on.--ChemSpiderMan (talk) 15:34, 25 January 2008 (UTC)

Diagrams

I noticed that the picure on the Terephthalic acid (benzene-1,4-dicarboxylic acid) page the image of the skeletal structure of the formula contained the Kerkulé structure of the benzene molecule, should this not be a ring in the centre instead of the 3 double bonds for accuracy? The image: -- Joestephens (talk) 23:35, 24 January 2008 (UTC)

That is a standard way of drawing phenyl rings in a skeletal formula - the aromaticity is implied. -- Ed (Edgar181) 23:39, 24 January 2008 (UTC)

I have seen only 3-5 structures on Wikipedia with the ring drawn inside the cycle and I would suggest they are removed and replaced with the alternating single/double display. I will make a note of them during my curation efforts as I see them.--ChemSpiderMan (talk) 23:53, 24 January 2008 (UTC)

IRC discussion on handling InChIs

We will be holding our next IRC meeting on Tuesday, January 29th at 1600h UTC. We want to decide how best to handle InChIs. I have posted a "request for comments" on the CINF listserve, so we can find out how people use information like SMILES and InChI on Wikipedia. Please join us at the IRC meeting! Walkerma (talk) 09:09, 26 January 2008 (UTC)

I have posted the responses to my questions here. There are nine sets of specific answers, and two other responses that are less specific to my questions (but still helpful). Please take a look before the IRC meeting if you can. Walkerma (talk) 05:03, 29 January 2008 (UTC)

Functional groups style guidelines

I'm trying to prepare a style guide for functional groups. This would include articles like alkane, alcohol, aldehyde, etc. Of particular interest (to me, at least), is the spectroscopy section - how do we identify and characterize these compounds?

I've prepared a skeleton here. Please take a look and expand/comment! --Rifleman 82 (talk) 10:13, 28 January 2008 (UTC)

Malathion

Hello all - while not officially part of the chemical project, I've been working on the malathion article for a little bit now, and it's page that apparently falls into your scope. When I initially came across it, it's POV was quite biased towards anti-pesticide views (references were quoted which were taken out of context, exagerated... etc). I did my best to clean it up, but I am worried that with prime mosquito season coming up in much of north america over the next few months, it could become the target of anti-pesticide groups again. This worries me, as there is a large debate in my hometown over the use of malathion (one of the few cites who still sprays with it), and I know many people look to Wikipedia as there source of info, especially since the Wiki page is the number one google hit for malathion. I myself don't have lot's of time to monitor the page, as I'm a medical student, and will be in northern Canada without internet access for several of the upcoming months. If I could get a little help monitoring the page for deviations from a neutral POV, that would be wonderful.--corvus.ag (talk) 15:57, 7 April 2008 (UTC)

Link pointing to compound rather than reaction removed. Are you sure?

User: ChemGardener removed "link pointing to compound rather than reaction":"[Cuneane|Metal-ion-catalyzed σ-bond rearrangement]" from Rearrangement reaction and from List of organic reactions. Are you sure that it was right correction? May be only one example of this reaction type is better than nothing? (Before somebody will write an article "Metal-ion-catalyzed σ-bond rearrangement".)--Tim32 (talk) 12:14, 29 January 2008 (UTC)

I would say that linking to the molecule is OK as long as the link is presented clearly. [Cuneane|Metal-ion-catalyzed σ-bond rearrangement] is misleading because the reader will expect a link to a reaction and instead gets an article about a molecule. I say just link it with the phrase: "Metal-ion-catalyzed σ-bond rearrangement, such as the rearrangement of cubane to cuneane". --Itub (talk) 13:02, 29 January 2008 (UTC)

May be Metal-ion-catalyzed σ-bond rearrangement: cubane to cuneane? Ok?--Tim32 (talk) 22:12, 29 January 2008 (UTC)

I took it out because of it seemed to be misleading. It would be fine to have some way of listing it in List of organic reactions, possibly as a red link to encourage creation, rather than as a pointer to the Cuneane article. There are other examples in the list where the article hasn't been created yet. One possibility would be: Metal-ion-catalyzed σ-bond rearrangement - such as Cubane to Cuneane. This would encourage creation of it and suggest inclusion of the Cuneane synthesis.

I would not put it in Rearrangement reaction as a red link or any type of link. I don't think it qualifies as a key rearrangement reaction at this point. - ChemGardener (talk) 19:18, 30 January 2008 (UTC)

Please, see I wrote metal-ion-catalyzed σ-bond rearrangement, but the problem still to be open for other reactions! I think, current WikiProject Chemicals community is unable to write single article for every reaction type.--Tim32 (talk) 16:56, 10 February 2008 (UTC)

Nice to see an article on this fascinating and large topic. As it currently stands, the article is barely a placeholder. So my recommendation is to shore up the science (and redraw the images uniformly and well) rather than worrying about linking. The title seems too cumbersome, which limits the article's impact.--Smokefoot (talk) 17:22, 10 February 2008 (UTC)

Thanks for nice! About "redraw the images": the images made by ChemSketch (free chemical structure drawing package that includes input and output in InCHI format) -- see, International Chemical Identifier#Software and services and please, compare with the images from Michael B. Smith, Jerry March, March’s Advanced Organic Chemistry, 5 th Ed., John Wiley & Sons, Inc., 2001, p. 1459. My images look better;) --Tim32 (talk) 19:16, 10 February 2008 (UTC)

Indexing of compounds

Sorry that I couldn't join you on IRC last night. However, on reading the discussion it seems that the problem of external access could be solved relatively easily by compiling indices of WP chem articles (as ChemSpiderMan and others have already done for personal use) and publishing them under a suitable licence. That way the "primary key", as far as WP is concerned, would become the name of the WP article and InChIs, CAS numbers etc would become secondary keys. This might seem like an awful lot of work (and it will be, doubtless), but it can be automated, both through {{chembox new}} and {{InChI}}.

The benefit would be that anyone could download and use the indexes in their products; our responsability, as it is now, would be to add data to pages which is as accurate as possible. What do people think? Physchim62 (talk) 19:26, 30 January 2008 (UTC)

I'm very intrigued by this, but I also don't properly understand your idea. Can you elaborate a little? Walkerma (talk) 05:44, 31 January 2008 (UTC)

The idea would be to run the search on a database dump to come up with a list such as:

7784-34-1|Arsenic trichloride

7732-18-5|Water (molecule)

which associates the identifier with a wikipedia article title (or URL). The indexes would be published, and could be used by anyone wishing to perform a search on one of those identifiers but not trusting Google or the MediaWiki search. Indexes can already be complied for {{Persondata}} (see Wikipedia:Persondata), the format on which {{InChI}} is based. Physchim62 (talk) 11:00, 3 February 2008 (UTC)

Test of automated article selection

Only rarely do I wear my WP:1.0 hat on this page, but I'd like to ask a favour. We have been testing a bot for selecting articles for offline release based on quality and importance assessments. We want an offline release of around 20,000-30,000 articles from all subject areas, and we want these to be picked based on a combination of importance and quality. Importance is considered more important than quality (we don't just want a collection including lots of FAs and GAs on trivia then find we failed to include Battle of Stalingrad, Spain or (heaven forbid!) organic chemistry. However, an FA like lead(II) nitrate would probably be included, because although it's not a really important topic, it is clearly non-trivial, and a very nice article.

We have a tentative selection of WP:Chem articles. A couple of comments: First, the hitranking is very rough, but should get much better. Second, there will be some articles that aren't on the list.

The articles are ranked in order of Score3; the three score options are based on a balanced combination of quality and importance. I'd really like to know if people think this would be an appropriate ordering of the articles, and if it would be a reasonable selection if we picked (say) all articles with Score3 >900 (or >800?). If the ordering is wrong, how have we got it wrong? Please comment! Thanks, Walkerma (talk) 06:21, 31 January 2008 (UTC)

After looking at the list, I would say that articles above 1200 are clearly very important. Below 1200 it is more of a mix, which starts to include comparatively obscure chemicals that presumably got in due to high article quality (which is not necessarily a bad thing!). The main issue I noticed is that some articles got in while others were excluded due to accidents of wikiproject classification. For example, we have chlorine, but not hydrogen, oxygen, nitrogen, or carbon. All of them are important, but apparently only chlorine is listed as a WP:Chemicals article while the others belong to WP:Elements. Similarly, some drugs, biomolecules, and polymers got in that are perhaps not as important as "chemicals" but are clearly important in their own categories. For example, paracetamol (but no aspirin?), vitamin K (but not vitamin C?), and polyester (but no polyethylene?). Finally, a few chemicals that come to mind that I think are important but missing from the list are the following (perhaps you can check what their rankings are and why): sodium carbonate (or sodium bicarbonate), calcium oxide (or calcium hydroxide), acetone, ethyl ether, and methanol. --Itub (talk) 12:05, 31 January 2008 (UTC)

Yes, there are definitely "must-have" articles like methanol that didn't make even it onto the list - if they did, I'm sure they'd have a high score. Our next list will be more complete, and have more accurate hit rankings (e.g. AlCl3 gets far more than the # indicated). As for elements, they are ALL in fact already on all our general releases, but the bot will pick them up through the Elements wikiproject. That chlorine is on our list is really an anomaly (though I accept that elements are chemicals too!). You're right about the less important ones, but we opted to make quality a factor too, as we have room for the occasional thing like Raney nickel. Thanks a lot for your excellent input! Walkerma (talk) 15:40, 31 January 2008 (UTC)

Redirect for N2O-N?

Hi! I was looking up some information on various greenhouse gases, and was pleased to see that somebody has put in redirects for most of the formulas I was looking for. However, I repeatedly came across mention of "N2O-N" in discussion of wastewater and soil, but couldn't find out much about it. Surely the main problem is that after 20 years my chemistry knowledge has faded greatly. But if somebody could put in a redirect to the proper name, I'd be much obliged. Thanks, William Pietri (talk) 08:00, 31 January 2008 (UTC)

N2O-N is N₂O. The exact meaning of -N is not clear from the publications, but has a meaning within the greenhous gas community.--Stone (talk) 09:40, 31 January 2008 (UTC)

I found this book that says it means "N2O measured in nitrogen units": [4]. For example, 1 pound N2O-N = 1.57 pounds N2O (because N2O is only about 63.6% N). --Itub (talk) 12:23, 31 January 2008 (UTC)

Fabulous! That eases my mind greatly. I was interpreting it as somehow having an extra nitrogen molecule along for the ride, and couldn't make heads or tails of the numbers from there.

After your explanation, the next thing I wondered was why people would do this. A pal tells me that often you'll know the quantity of something before a reaction. E.g., if you have a ton of coal, you know you'd have n kilos of carbon. After burning, you assume you'd have n kg CO2-C, or 44/12x kg CO2. Still seems a little wonky to me, but I'm sure many things in my profession would seem equally wonky to outsiders.

So thanks! I'll leave it to you guys to figure out whether this info has any place in Wikipedia, as I'm way out of my depth. William Pietri (talk) 21:41, 31 January 2008 (UTC)

You are right this nomenclature of the strange atmospheric chemists has to have a place somewhere!--Stone (talk) 22:02, 31 January 2008 (UTC)

It's actually quite a common way of expessing analytical results, although it's the first time I've seen it used for nitrous oxide. Physchim62 (talk) 14:09, 1 February 2008 (UTC)

Indigo dye

I put up a Chembox new onto the page of Indigo dye, but it is little bit short and the two possible CAS numbers 482-89-3 or 12626-73-2 are also not the standart I wanted to have. So I left it hiding untill somebody is able to help.--Stone (talk) 09:31, 31 January 2008 (UTC)

According to NIST, the first of these CAS numbers is the correct one, while the second refers to the isomer where the two carbonyl groups are cis to one another. I have edited the article accordingly. Physchim62 (talk) 16:05, 31 January 2008 (UTC)

two lead(II) oxide articles

There are two articles lead(II) oxide and lead (II) oxide for PbO. The former is much the better article and reflects a lot of concerted editing. Can someone with the power/knowledge delete the lead (II) oxide article please.--Axiosaurus (talk) 16:53, 2 February 2008 (UTC)

Thanks RM--Axiosaurus (talk) 17:42, 5 February 2008 (UTC)

Some renaming of articles

We have an article tin dioxide which should probably properly be called Tin(IV) oxide.
There is an article red lead which should be probably be called Lead(II,IV) oxide, with red lead becoming a redirect.
With the compound PbCO₃ we have an interesting(?) situation;lead(II) carbonate redirects to cerussite; we have a separate article for white lead,an alternative name PbCO₃; lead carbonate links to cerussite. I guess we should really have a chemistry page for lead(II) carbonate, a mineral page for cerussite, and make white lead and lead carbonate redirects to lead(II) carbonate. Opinions anyone? If needed I am happy to do the lead(II) carbonate article if that is what is agreed. --Axiosaurus (talk) 17:41, 5 February 2008 (UTC)

Why is tin(IV) oxide preferred over tin dioxide for SnO₂?

Ben (talk) 19:07, 10 February 2008 (UTC)

I too vote for tin dioxide over tin(IV) oxide (and for titanium dioxide over titanium(IV) oxide, and for acetic acid over ethanoic acid, etc., etc.) Yikes. Now Axiosaurus's questions about red lead and the minerals are more complicated issues ... Suggestions are also sought for an improved name for the article with the unfortunate name Metal-ion-catalyzed σ-bond rearrangement (hmm... maybe we need "proton-induced conversion of amines to ammonium cations") --Smokefoot (talk) 19:22, 10 February 2008 (UTC)

I've redirected lead(II) carbonate to lead carbonate, and I have moved white lead to lead carbonate over the redirect. I hope that solves the problem. --Rifleman 82 (talk) 19:27, 10 February 2008 (UTC)

About Metal-ion-catalyzed σ-bond rearrangement: this name has been gotten from the book "Michael B. Smith, Jerry March, March’s Advanced Organic Chemistry, 5 th Ed., John Wiley & Sons, Inc., 2001, p. 1459." Another name (such as "proton-induced ...") may be WP:NOR problem...--Tim32 (talk) 20:07, 10 February 2008 (UTC)

Well I'm a little surprised guys --looks like the convention for IUPAC naming of compound articles ha staken a knock. I don't mind myself--I'm very old and prefer the good old names! thanks for the lead carbonate redirects -RM I'll put PbCO
₃ on the to do list. (Note use of {{chem|Pb||C||O|3}}. I've not used this new to me template before--does anybody else?)--Axiosaurus (talk) 10:10, 12 February 2008 (UTC)

Rosocyanine

The article has been tagged to be split since 2006. I think that a decision should be taken whether to split or not soon. -- 217.11.34.119 (talk) 22:39, 9 February 2008 (UTC)

I created a stub for rubrocurcumin. Unfortunately, I did not find the CAS number and other properties. --Leyo 20:30, 26 February 2008 (UTC)

I added in CAS#, formula, and mass. -- Ed (Edgar181) 20:53, 26 February 2008 (UTC)

Great. Where did you find the CAS#? It's not included in PubChem and other databases I tried. Can you also check if the CAS# 37204-72-1 for rosocyanine is correct? Thanks in advance. --Leyo 21:15, 26 February 2008 (UTC)

I get CAS numbers directly from CAS using SciFinder. 37204-72-1 is correct for rosocyanine. -- Ed (Edgar181) 21:27, 26 February 2008 (UTC)

Unfortunately, I don't have access to SciFinder. I have now changed Rosocyanine to a single-substance article as it was suggested. --Leyo 00:30, 27 February 2008 (UTC)

InChIKey resolver

Folks here may be interested in a very lively discussion on the ChemSpider blog here. It's a long post, with loads of replies, but very interesting. Here's the gist:

• InChIKeys are very handy things for structure searches on the web. They can allow you to do (in effect) a structure search on the web!
• However, if you find an InChIKey separated from a structure, you can't convert it to a structure or even an InChI - the hash only works one way. This can be a problem if you do a search like this and find a hit like this which has simply a list of InChIKeys and a set of structures. Which is which?
• Wouldn't it be nice if we could resolve these, just like we can with a DOI?
• An InChIKey can (in effect) be resolved using a lookup table, as used here. But what if it's not in ChemSpider? There needs to be a more comprehensive system for resolving these.
• How should such a system be organised - one central location or in a "federal" system? Where should/would such a system be located - PubChem? CAS? IUPAC? ChemSpider?
• Antony (aka (User:ChemSpiderMan) is considering making this his next big thing to work on.

I think a lot of the issues raised here are useful as we try to coalesce our ideas on structural representation on Wikipedia. Walkerma (talk) 19:13, 12 February 2008 (UTC)

Pseudohalogen Names

Cyanogen chloride, Cyanogen bromide, Iodine cyanide should get consistent names.--Stone (talk) 19:43, 12 February 2008 (UTC)

• Which? As I read the IUPAC names in the articles, they aren't consistent. But what about cyanic chloride, cyanic bromide and cyanic iodide? Wim van Dorst (talk) 22:08, 12 February 2008 (UTC).

If I had a clue I would have done it, but with this inorganic stuff! Iodcyan was my guess, but in the wrong language.But with all possible redirects I would start.--Stone (talk) 22:52, 12 February 2008 (UTC)

Is this one of these electronegativity issues like we see with oxygen difluoride vs. dichlorine monoxide? I know that ClCN and BrCN are commonly named as cyanogen halides, and the halide is the electronegative part. A Google search gives both names for ICN, but I'm pretty sure the CN is the more electronegative part of the pseudohalogen. In my perusings I also stumbled across another related stub called cyanogen halide. I'd like to get the view of an inorganic chemist on this (Smokefoot? Axiosaurus?) Walkerma (talk) 04:35, 14 February 2008 (UTC)

My personal experience of using or sourcing any of these compounds is zero so no help there. I do not even know what the official IUPAC name is -- their documents are very legal and rather dense - and so am I. My vote, for what it is worth, is for the cyanogen halide name - purely on my impression that it is more common for suppliers , recent patents and papers. (Wiberg, Greenwood and Cotton all very carefully sit on the fence on this - giving both names) Consistency is the key - we are in good company- whatever we do. As long as the non chosen name is first in the other names list and is mentioned in the lede. After all guys you voted for tin dioxide rather than tin(IV) oxide!--Axiosaurus (talk) 18:51, 14 February 2008 (UTC)

Classes of chemicals

I was simply wondering if pages could be made for classes of chemicals that were all chemically similar, such as C₃O₂, C₄O₂, and C₅O₂, which I also happened to notice was not in this project. I'm not exactly sure what this class of chemicals is called, as I'm somewhat new to chemistry, and if there are pages for classes of chemicals, I would like to create this one, whatever it is called.--IdiotsOpposite (talk) 00:57, 13 February 2008 (UTC)

I would call the class "carbon suboxides". We do have an article on the first compound, which is called carbon suboxide. Perhaps the others can be added to that article as well, unless there is enough information to have separate articles for each. --Itub (talk) 07:58, 13 February 2008 (UTC)

not every chemical deserves its own page, take for example a look at boronic acid or xylene V8rik (talk) 19:51, 13 February 2008 (UTC)

Thanks for the info guys, and thanks also to Smokefoot, who posted in my talk page about this question. I'm also going to start work on the stub article β-carotene, and since it started first, it takes preference. However, I might make a section in the carbon suboxide article after I work on β-carotene. I make no guarantees, but I'll try to do what I can.--IdiotsOpposite (talk) 23:09, 13 February 2008 (UTC)

Well, replying again with comments and questions. I've worked a little on the carbon suboxide molecule. I skipped β-carotene after I saw that it was listed under "biochemistry", not "chemicals". I mainly added things in the chembox and a small amount of content change. However, I noticed that carbon suboxide is not in the worklist. I don't have a problem with that, but why is carbon suboxide within the scope of WikiProject Chemicals and yet not in it's worklist? I think that it should be added. —Preceding unsigned comment added by IdiotsOpposite (talk • contribs) 00:41, 14 February 2008 (UTC)

Thanks for joining us and helping out! The worklist contains a collection of around 380 articles that we targeted, in order to ensure we had a good, representative selection of major topics covered. There are actually something like 5000-7000 articles on chemicals in total (though many aren't tagged as yet) - that bigger list is here. It certainly doesn't mean that these other compounds don't matter, the worklist was just to provide some focus. The suboxides article would be a useful addition. Thanks! Walkerma (talk) 02:04, 14 February 2008 (UTC)

• There are two wikiprojects relevant here: Chemistry and Chemicals. Of course they closely work together and effectively editors work on articles out of both interest scopes. Typically I rate real chemical compounds against Chemicals and groups or classes of chemical compounds against Chemistry, same as I would rate articles for discoverers of chemicals or important reactions of chemicals. In the basic, the WP:Chem is to provide a huge dictionary with chemical (and physical) details of chemical compounds. All interesting Chemistry topics are being discussed in other wikiproject (e.g. Elements) or in the mother wikiproject of Chemistry.
• The worklist, dating from 2005(!), was the start of the Wikiproject Chemicals, generally known as WP:Chem, allowing us to get a fair coverage of all chemical compounds in the world with at least a serious number of representing chemicals. This list has been fixed since Summer 2006, so unless there is a serious omission in the setup of the list, I would propose to stick to it.
• All that does still mean: please be welcome to work on any article you would like, either in the WP:Chem (worklist or not), or in the Chemistry wikiproject. Any contribution towards a better coverage of the whole wide field of Chemistry, including elements, chemicals and other sub-wikiprojects, is a Good Thing^TM. Wim van Dorst (talk) 16:11, 17 February 2008 (UTC).

Amiloride

The structure provided on the amiloride page is wrong. It should have four primary amine groups, but each is shown as simply an N atom at the end of a single bond. I have no idea about uploading graphics (haven't explored that yet, and don't have time to do so now). So, would someone please ChemDraw (or whatever) a corrected structure and upload a replacement image? Thanks, EdChem (talk) 15:01, 14 February 2008 (UTC)
The structure on the Esmolol page is even worse, BTW. EdChem (talk) 15:19, 14 February 2008 (UTC)

Fixed, with Edgar181's help. --Rifleman 82 (talk) 15:38, 14 February 2008 (UTC)

Looks like we were doing the same thing at the same time. I was trying to figure out what the problem with esmolol was, before realizing you had already uploaded a fixed version. :) -- Ed (Edgar181) —Preceding comment was added at 15:43, 14 February 2008 (UTC)

Thanks to you both. :) EdChem (talk) 15:46, 14 February 2008 (UTC)

Just a reminder, there are lots more that still need fixing. And glucose is another complete mess we need to fix soon, see these comments. The battle goes on! Cheers! Walkerma (talk) 17:39, 14 February 2008 (UTC)

I am the creator of Image:Amiloride structure.svg (now fixed), and just wanted to say I'm always willing to fix any errors found in my SVGs. Or even make new ones from scratch. Just drop a note on my talk :-) ›mysid (☎∆) 19:52, 14 February 2008 (UTC)

Laboratory synthesis

Is there a rule not to keep (too detailed) sections on laboratory synthesis? If not this old edit should be reverted. Thanks. --Leyo 20:09, 19 February 2008 (UTC)

Well, Wikipedia is not an instruction manual, so I would think it isn't a lab manual either. That's something that's bothered me about SPSS also. Would be good to establish an explicit guideline in the chemistry realm, since some processes, reactions, conditions, etc are relevant and important content in their own right. DMacks (talk) 20:18, 19 February 2008 (UTC)

• gah*, make that SPOS, which actually isn't the bad one I had in mind. Let's try Peptide synthesis#An example of solid phase peptide synthesis as an example of excessive. DMacks (talk) 21:21, 19 February 2008 (UTC)

In de-WP (my home WP), we have a directive on this topic. According to it, we do not allow such detailed descriptions of synthesis like the example above. --Leyo 00:51, 20 February 2008 (UTC)

To me the Laboratory synthesis of HBr section is permissible and it should be reinstated. It would be a manual if the text would go like dissolve 10 grams of A in 100 ml of B and stir for 1 hour at 34 degrees etc. V8rik (talk) 21:16, 19 February 2008 (UTC)

On a related topic, I like the approach that laboratory syntheses are described separately from the industrial routes, but I think that the latter should be emphasized when possible.--Smokefoot (talk) 23:38, 19 February 2008 (UTC)

I've re-added the section (BTW, I never think twice about undoing unexplained deletions of entire sections by IP users!). There's nothing wrong with mentioning methods of synthesis and giving a few chemical equations. As V8rik says, this is not like a lab manual at all; a manual (or the experimental section of a paper) would be step-by-step and give specific amounts, times, conditions, equipment, and details such as methods of stirring and separation. --Itub (talk) 05:18, 20 February 2008 (UTC) I just looked at the peptide synthesis article and that one is a perfect example of manual-like writing which goes against policy. --Itub (talk) 05:24, 20 February 2008 (UTC)

I just added a paragraph about this to the style guide.[5] How does that look? --Itub (talk) 10:32, 20 February 2008 (UTC)

Looks great. --Rifleman 82 (talk) 14:15, 20 February 2008 (UTC)

Butylene

This article isomers of butylene is out of harmony with the text, which mostly uses butene. I would like to rename it as just Butene and expand its contents which are quite thin atm--AssegaiAli (talk) 16:15, 23 February 2008 (UTC)

Wikipedia's style is to name articles with the most frequently used name, and for chemicals this generally has meant preferring common names over systematic/IUPAC names. The current title of the article "Isomers of butylene" is unecessarily cumbersome, and has no advantage over either "butene" or "butylene", so I would certainly favor a name change in that case. It doesn't matter too much to me whether it ends up at butene or butylene, but I think it would be a good idea to have consistent naming of the series ethene/ethylene, propene/propylene, butene/butylene, etc. As far as I know, the only one that has been discussed extensively is ethylene. Consensus in that case was to stay at "ethylene" because it is by far the more commonly used name, even though "ethene" is the systematic name. -- Ed (Edgar181) 20:42, 23 February 2008 (UTC)

Diisopropyl fluorophosphate

Could an admin move diisopropylfluorophosphate to diisopropyl fluorophosphate? The latter would be in line with the salt nomenclature typically used for esters, e.g. triethyl phosphate.

I tried make the move myself, but was foiled by the redirect at diisopropyl fluorophosphate.

Ben (talk) 20:03, 1 March 2008 (UTC)

I'll point you to WP:RM, which handles these sorts of things. Best, shoy 22:54, 1 March 2008 (UTC)

Erm, it's been done hours ago. --Rifleman 82 (talk) 04:58, 2 March 2008 (UTC)

X-Pro

Before I nominate it for AfD, perhaps somebody would like to save this confusing redirect/disambig/stub. --_{Piotr Konieczny aka Prokonsul Piotrus| talk} 15:52, 3 March 2008 (UTC)

Ah, I speedied it. WP is not a dictionary/directory/whatever; at this point we should concentrate on "real" articles. --Rifleman 82 (talk) 16:01, 3 March 2008 (UTC)

adding IUPAC 2005 names to organometallics

I have made a start checking through organometallic IUPAC names and checking them against the 2005 IUPAC inorganic recommendations (full text of the red book is 4.13MB pdf @ http://www.iupac.org/publications/books/author/connelly.html).
Before I get going in earnest I'd appreciate opinions on the best looking version of the name. The example is diiron nonacarbonyl and the issue is the appearance of the dashes used as separators in the name. (The chembox in the aricle shows my first effort and the problem)

1. tri-μ-carbonyl-bis(tricarbonyliron)(Fe-Fe) all dashes using the keyboard minus key "-"

2. tri−μ−carbonyl−bis(tricarbonyliron)(Fe−Fe) all dashes using the "&minus"

3. tri—μ—carbonyl—bis(tricarbonyliron)(Fe—Fe) all dashes using the long dash selected in the wiki editor i.e below the preview window

Personally I prefer a mixture of &minus for the literal portion and long dash for the metal metal bond suffix i.e.

tri−μ−carbonyl−bis(tricarbonyliron)(Fe—Fe)

I only have Firefox and IE7 so how do these look in other browsers? --Axiosaurus (talk) 20:41, 5 March 2008 (UTC)

Why would you use a minus sign instead of a hyphen? They do not mean the same and have different usage conventions. As far as I know, chemical names normally use hyphens, but bonds in text (for example, when you say "Fe–Fe" bond) use en dashes. If you can, look at the ACS style guide which has a lot of good (IMO) recommendations about use of hyphens, en dashes, em dashes, an minus signs. --Itub (talk) 05:56, 6 March 2008 (UTC)

I always use en dashes when "describing" bonds (e.g. in an image title), as Itub suggests. Fvasconcellos (t·c) 15:41, 8 March 2008 (UTC)

Which apostrophe?

Hey everybody, I am active in german wikipedia's Chemistry Project and recently I found an article using uncommon apostrophes in the title: de:8’-Apo-β-caroten-8’-al. So I asked myself, which kind of apostrophe should be used in names of chemical substances. I didn't find any answer yet, but perhaps you can help me. Thanks, --NEUROtiker (talk) 21:26, 5 March 2008 (UTC)

The symbol to be used should be a prime (') as in 1,1'-Bi-2-naphthol, not an apostrophe (’) as in de:8’-Apo-β-caroten-8’-al. In some fonts they may look the same though. -- Ed (Edgar181) 01:10, 6 March 2008 (UTC)

Thanks. Do you know any source which I could refer to? Some typographic or IUPAC guideline or similar? --NEUROtiker (talk) 23:29, 7 March 2008 (UTC)

That is what is recommended in the ACS Style Guide. But this may actually be much more complicated than I thought because different fonts depict those two symbols in different ways. For example, when I look at this page, the two symbols look the same - both are vertical lines. When I look at the text in the edit window, the prime is vertical and the apostrophe is slanted up to the right. On another computer I use, the prime is slanted and the apostrophe is curved. The depiction of the prime in the ACS Style Guide is slanted. -- Ed (Edgar181) 12:02, 11 March 2008 (UTC)

An interesting side-issue for WP: how does one bold or italicize it, given that the character is the same as the wiki-markup mark? For example, N,N'-dimethylformamide should have the "N" in italics (not sure about the prime mark), but "''N'',''N'''-dimethylformamide" is broken. What HTML or other entity code is this character? -- User:DMacks 15:32, 11 March 2008 (UTC)

I think you could use the code '&prime;' (actually typing this code without it being convertised is actually already an interesting task), this gives ′. --Beetstra (public) (Dirk Beetstra^{T C} on public computers) 18:22, 11 March 2008 (UTC)

testing: N,N′-dimethylformamide .. works. --Beetstra (public) (Dirk Beetstra^{T C} on public computers) 18:23, 11 March 2008 (UTC)

N,N′-dimethylformamide N,N′-dimethylformamide N,N′-dimethylformamide super! DMacks (talk) 19:45, 11 March 2008 (UTC)

Excpet that DMF has only one nitrogen, so it doesn't need a prime at all...  :) -- Ed (Edgar181) 19:54, 11 March 2008 (UTC)

Well yeah, it's a crappy example:) Maybe WP is smart enough to know "you're doing it wrong"? DMacks (talk) 19:56, 11 March 2008 (UTC)

Sodium lauryl sulfate has incorrect image

In looking at the image on sodium lauryl sulfate:

it appears to be missing the sodium atom at the right end. Please respond on Talk:Sodium lauryl sulfate#Incorrect image if I'm wrong (or right!) and feel free to fix the article. Cburnett (talk) 02:07, 7 March 2008 (UTC)

WikiChem

Folks, I have been watching the pain of dealing with CAS. Would anyone be interested in helping build a Wikimedia project that would be free to all and end our reliance on CAS? Geoff Plourde (talk) 22:00, 9 March 2008 (UTC)

Our reliance on CAS is minimal, and their attempts to restrict our use of CAS information are probably illegal. Physchim62 (talk) 12:39, 10 March 2008 (UTC)

I agree with PhysChim62 - there is no reliance on the CAS Numbers. There is value but no reliance. Articles would be valuable without the numbers but there is definitely additional value in having the numbers. If you would like to get involved in a project other than WP:Chem then you might want to connect with me offline. We are working on WiChempedia as discussed here. --ChemSpiderMan (talk) 00:29, 11 March 2008 (UTC)

CAS and Wikipedia

CAS, a division of the American Chemical Society, is pleased to announce that it will contribute to the Wikipedia project. CAS will work with Wikipedia to help provide accurate CAS Registry Numbers^® for current substances listed in Wikiprojects-Chemicals section of the Wikipedia Chemistry Portal that are of widespread general public interest.

The CAS Registry is the world’s most comprehensive collection of chemical substances and the CAS Registry Number is the recognized global standard for chemical substance identification.

CAS views Wikipedia as an important societal tool for the general public, and this collaboration with Wikipedia is in line with CAS’ mission as a Division of the American Chemical Society.

We look forward to working with the Wikipedia volunteers over the next few weeks to make this happen.Eshively (talk) 13:44, 12 March 2008 (UTC)

Periodic acid

I've given it a chembox, somewhat arbitrarily choosing the solid dihydrate form (H5IO6) instead of HIO4 which the article states, exists in solution or after dehydration of the orthoperiodic acid. Take a look and comment, please? --Rifleman 82 (talk) 15:52, 15 March 2008 (UTC)

Perhaps phosphoric acid, which has ortho and meta forms, is relevant. --Rifleman 82 (talk) 15:56, 15 March 2008 (UTC)

Iodine acids form a series H₅IO₆, orthoperiodic acid; HIO₄, periodic acid; HIO₃, iodic acid; HIO₂, iodous acid; HIO, hypoiodous acid. Funnily enough IUPAC 2005 allows these names as they are systematic. --Axiosaurus (talk) 17:34, 15 March 2008 (UTC)

I should have added that H₅IO₆, HIO₄, HIO₃ can be isolated as solids. Also in addition to the formally named acids there are some others I should have mentioned e.g. H₇I₃O₁₄,"triperiodic acid" and H₃IO₅, "mesoperiodic acid" neither of which can be isolated; and HI₃O₈, "anhydro-iodic" acid a solid adduct of HIO₃ and I₂O₅. --Axiosaurus (talk) 10:22, 16 March 2008 (UTC)

With all respect, Axiosaurus, are you sure about what you've written? The non-hydrated formula for iodic(VII) acid would be HIO4, but I regularly see it written as H5IO6: I am quite willing to believe the latter formula. The iodine atom is large and it would be normal to expect it to have octahedral coordination and not tetrahedral coordination: see, for example telluric acid. Physchim62 (talk) 16:21, 19 March 2008 (UTC)

Oh ye of little faith! Orthoperiodic acid,H₅IO₆, X-tal structure shows a straightforward monomeric complex of octahedral iodine with 1=O and 5 -OH groups. Solid HIO₄ on the other hand has a chain, polymeric sructure (see Wiberg & Holleman) edge shared octahedral, I bridged by O atoms and non bridging O and OH groups. (this was new to me I must have missed that one somewhere along the way) Your instinct about octahedral was quite right. (However IO₄⁻ IS tetrahedral with a bond length of 178pm (see Greenwood)). The naming of these acids has been a bit patchy. Older books I have call them all "periodic acids" . 1966 cotton and wilkinson calls H₅IO₆ paraperiodic acid, and the IO₄⁻ ion metaperiodate, which tallies with Wiberg which gives metaperiodic as an alternative name for HIO₄. HIO₄ is difficult to prepare from what I can read - I shall try to follow up the original paper as I am intrigued. H₅IO₆ according to Wiberg can be used to prepare a variety of iodate, "periodate" salts depending on conditions e.g. salts containing the following IO₄⁻, H₄IO₆⁻, H₃IO₆²⁻ H₂IO₆³⁻ and IO₆⁵⁻. Greenwood quotes some equilibrium constants for the various HnIOm species in aqueous solution.--Axiosaurus (talk) 19:34, 20 March 2008 (UTC)

Cesium hydride

This article is at AfD. It has recently been created and is really only one sentence. It should of course also be renamed to Caesium hydride. --Bduke (talk) 06:46, 21 March 2008 (UTC)

Element names and Aluminum

I'd like to formally request that this wikiproject note that the spelling of the element "aluminum / aluminium" be restricted to the international version only in chemical related articles, not generally throughout the encyclopedia.

An overzealous editor has just tried to apply this to the entirety of the engineering usage articles, including the rather ludicrous spelling change of the "Aluminum Association", the US trade group, to "Aluminium Association". This is just not appropriate or acceptable. The guideline has to be limited in scope to the reach that the name actually has. Georgewilliamherbert (talk) 19:14, 21 March 2008 (UTC)

If you'll look at my contributions, you'll see that I've restricted my spelling changes to articles that are chemistry-related. I think WP:ENGVAR takes precedence for other articles. I've been making a conscientious effort to apply the spelling changes only to where it is appropriate, such as not making changes to links, journal titles, etc. If among the thousands of spelling corrections, I have made an error, I apologize. You simply need to politely point out the mistake and I'll correct it. It's ridiculous to suggest rolling back all my changes. I think articles on alloys are clearly chemistry-related articles, but I can see that others might disagree. If you disagree, I'm willing to politely discuss it, if you are. Element16 (talk) —Preceding comment was added at 19:26, 21 March 2008 (UTC)

Caesium v cesium

Efforts to make the spelling of the element Caesium consistent has met with opposition by editors of Global positioning system on the grounds that a caesium clock is known as a cesium clock in the USA and as GPS was invented in the USA then WP:ENGVAR should take precedence over WP:SULF. I would welcome comments on the discussion page of Global positioning system. Thanks Velela (talk) 00:42, 22 March 2008 (UTC)

Shortcut

What about creating a shortcut for Wikipedia:WikiProject Chemistry/Structure drawing? I would have proposed WP:CSD, but it is already in use. --Leyo 15:55, 24 March 2008 (UTC)

What about WP:CSDG (Chemical Structure Drawing Guide)? 212.41.125.139 (talk) 02:50, 29 March 2008 (UTC)

Done. I also added WP:Chem/Structures. Physchim62 (talk) 14:02, 29 March 2008 (UTC)

Strem

Started a new article, do take a look: Strem Chemicals. --Rifleman 82 (talk) 15:34, 26 March 2008 (UTC)

Looks like a perfectly good stub to me, and the company is notable. However, you may want to add some independent sources preemptively, because short articles about companies are often nominated for deletion within hours by people who doubt the notability of the company. --Itub (talk) 15:42, 26 March 2008 (UTC)

MPTP IUPAC name

Most sources use the name "1-methyl 4-phenyl 1,2,3,6-tetrahydropyridine" for MPTP, but PubChem reports as IUPAC name computed from the structure "1-methyl-4-phenyl-3,6-dihydro-2H-pyridine". Is PubChem right and everyone else wrong, or is this a bug in PubChem's algorithm? AxelBoldt (talk) 14:25, 28 March 2008 (UTC)

Both appear to acceptable IUPAC names (if you add the necessary hyphens to the first one), although I prefer the PubChem version as it avoids the "1-hydro" in the other version: it isn't a hydrogen atom in the final structure, it's a methyl group, even if it starts out as a hydrogen in the "parent hydride" from which that name has been derived. The downside of the PubChem name is that most people are not familiar with the rules for "indicated hydrogen" which you need to know to make sense of the name. Physchim62 (talk) 16:37, 28 March 2008 (UTC)

Are skeletal formulae PD-ineligible?

A bot on Commons is converting the permission of every skeletal formula it can find to PD-chem (This image of a structural formula is ineligible for copyright and therefore in the public domain, because it consists entirely of information that is common property and contains no original authorship.).

Are skeletal formulae automatically in the public domain? There are often many different ways of drawing a skeletal formula, and the one chosen requires skill and judgement on the part of the author, to get maximum clarity. I know that the law on copyright varies greatly from country to country (Germany, for example, requires a lot of originality to make something copyrightable) - which law applies to the Commons - Florida law?

What about reaction schemes? And 3D images?

Ben (talk) 16:48, 31 March 2008 (UTC)

My feeling is that some skeletal formulae may not be eligible for copyright, but that many are. Therefore converting them all by bot without using judgement is a very bad idea. -- Ed (Edgar181) 16:54, 31 March 2008 (UTC)

Some formulae (methane, for example) are pretty certainly ineligible for copyright. However, that doesn't mean we should be saying that all formulae are. We've done very well so far with licensed chemical structures, and I have gone so far as to nominate the badly-worded (IMHO) copyright tag for deletion here. Physchim62 (talk) 17:28, 31 March 2008 (UTC)

Fulvalene

fulvalene or pentafulvalene. A microreviw doi:10.1002/ejoc.200500231 and a article [6] suggest, that this is pentafulvalene not fulvalene. And the first synthesis was done 1915doi:10.1002/cber.19150480136. So should we rename it or change the article to a article about all possible fulvalenes?--Stone (talk) 17:26, 7 April 2008 (UTC)

• Synthesized by Matzner / Doering in 1958 but never published? What is going on here....V8rik (talk) 21:04, 7 April 2008 (UTC)

Orbitals in italics?

The standard way of typographically representing orbital types seems to be in italics, i.e. 1s². Is this actually the standard? Many examples in WP use non-italicised letters. So, I guess my questions are a) does WP:Chem have a standard on it, and b) is it important enough? I've edited a couple of articles whilst browsing but if it's not that important I won't edit this in future. Cheers Freestyle-69 (talk) 07:47, 9 April 2008 (UTC)

The ACS Style Guide (used by the journals of the American Chemical Society) uses lowercase roman letters for atomic orbitals such as s, p, d, and f. I don't know if other publishers use italics. I generally try follow the ACS style on Wikipedia unless there is explicit consensus to do otherwise. --Itub (talk) 10:02, 9 April 2008 (UTC)

I think they should be in upright type and not italic, although I haven't yet found an external authority for that. Originally, the letters were abbreviations for spectroscopical terms (sharp, principal, diffuse, fine), and such abbreviations are usually printed in upright type. AFAIK, there are no specific guidelines on WP, and I have seen italic type used (I've used it myself, on occasions). I don't think it's a problem in general articles, but I note that atomic orbital uses both upright and italic type, something which should probably be changed for that article at least! Physchim62 (talk) 13:53, 9 April 2008 (UTC)

IUPAC agrees with both Itub and I (and, incidentally, the ACS): International Union of Pure and Applied Chemistry (1993). Quantities, Units and Symbols in Physical Chemistry, 2nd edition, Oxford: Blackwell Science. ISBN 0-632-03583-8. p. 83. Electronic version. I don't have access to the definitive version of the third edition (2007), but I do have a review copy (2005) and the relevant paragraph is identical. Physchim62 (talk) 15:34, 9 April 2008 (UTC)

I'm happy either way. It'd be nice if we had a standard way of doing it on WP (and so it seems that it should be non-italicised), how do we go about setting it in stone? Freestyle-69 (talk) 05:59, 10 April 2008 (UTC)

Am. Chem. Soc. does not italicize electron configuration, e.g., d⁶ complexes but does so in 16e complex. Point groups are italicized, C_2v. Symbols for variables appear to be always italicized: E (for energy), T₁ (NMR), t_1/2, d_Fe-Fe = 2.51 Å, pK_a, ΔH, ΔS, ΔG. But we should check with the Chemical Soc. and the Euro area policies before deciding.--Smokefoot (talk) 13:26, 10 April 2008 (UTC)

I'm happy to draft guidelines based on the IUPAC Green Book if people tell me where the problems are. In general, physical quantities are in italics, whereas mathematical symbols are in upright type, although there are exceptions—at least, cases which could be seen as exceptions if you don't follow the strict definitions as to what is "physical" and what is "mathematical"! "e" for an electron should be (according to IUPAC, IUPAP and the ISO) in upright type if referring to the particle ("16e-complex") but in italics if referring to the elementary charge, a distinction which is rarely relevant in chemistry. I don't think this is a difference between Europe and North America, but rather between different editors (of both and other regions) who happen to prefer one form over the other. It doesn't seem important for the scientific content (nor for the organization) of WP, but it would be nice if each individual article could be self-consistent! Physchim62 (talk) 16:02, 10 April 2008 (UTC)

Cheers everyone. For the moment I'll just aim at consistency within articles. Freestyle-69 (talk) 00:12, 11 April 2008 (UTC)

Box width

I found this via Special:Random - I think the issue should be self-explanatory. How can this be dealt with on a systematic basis? --Random832 (contribs) 16:27, 18 April 2008 (UTC)

On most browsers, that page looks just fine. However, on some browsers long names and/or SMILES in the infobox can cause the width to be too big. An easy solution is to add spaces in the middle of the data causing the problem. I have fixed it for that article. -- Ed (Edgar181) 12:12, 20 April 2008 (UTC)

Free drawing software?

My apologies if this question has been asked before. Is there a structure/reaction drawing program a la ChemDraw that's available for free online and that works on Macs? I'm on an iBook G4 running OS 10.5.2, and I haven't been able to find anything. I'm not looking for anything fancy, I'd just like to be able to add some structures and perhaps rxn schemes to some articles. Yilloslime (t) 04:47, 20 April 2008 (UTC)

I believe there is a free version of MDL ISIS/Draw for the Mac. (If you can't find it via Google, let me know, and I'll look for it.) -- Ed (Edgar181) 12:14, 20 April 2008 (UTC)

Try ACD/ChemSketch I believe it is free for non-comercial use, but check out the licience. Works on Windows fine - Quantockgoblin (talk) 07:19, 24 April 2008 (UTC)

Thanks for the ideas. Unfortunately, I've downloaded both and neither of them seem to work on my 'puter. The ACD program appears to be Windows only—at any rate, my computer has no idea what to do with a .exe file. MDL does have a Mac version, but it hasn't been updated since Feb 2001, so again, my computer just looks at the file dumbfounded. You'd think that apple.com would have some basic drawing program available for free here, but, alas, no. Any other ideas? Yilloslime (t) 18:07, 3 May 2008 (UTC)

On a limb here, but I believe Linux/Unix software can be made to work on a Mac? Not that I know from personal experience. Check Chemtool.[7]. --Rifleman 82 (talk) 18:16, 3 May 2008 (UTC)

If the source code it available, it can usually be compiled on Mac. Sometimes it "just works", sometimes it takes somewhere between a tweak and an infinite amount of hacking to get it to compile and run properly. Fink and MacPorts both have extensive collections of science programs (last I knew, fink had a wider selection, but some were older versions). DMacks (talk) 18:37, 3 May 2008 (UTC)

Propylene or propene

I made what I thought would be an uncontroversial move of propene to propylene, only to have it promptly reverted.

What do you chemists out there think is the more appropriate title? It seems strange to have ethylene but propene. A quick Googling returns 315,000 for propene and 4,510,000 for propylene. I know the Google test is crude, but at 14 times as many hits for propylene, it's fairly clear.

Ben (talk) 22:53, 23 April 2008 (UTC)

You make a good point comparing this to Talk:Ethylene#Title and name Ben. It seems that because this isn't something that is cut and dried, there just needs to be a consensus on the topic. I'm for propylene personally. Freestyle-69 (talk) 23:31, 23 April 2008 (UTC)

Another way to go is to use the IUPAC name. However, often IUPAC names are not the most commonly used and too much of a mouthfull! Apart from raising this as an option, I'm not sure I've really contributed! That said, I think that as long as people can find the page under either name, maybe we shouldn't worry too much about what exactly it is called ~ instead let’s find some juicy pages to upgrade! Maybe others think otherwise? -- Quantockgoblin (talk) 23:46, 23 April 2008 (UTC)

Chemistry has a long, rich, and fascinating history, as reflected by the various non-IUPAC (common, trivial, obsolete, trade, etc.) names for older chemicals. If we were to always use IUPAC names, we'd certainly be more consistent, but we'd also remove wikipedia a step or two from this history. Wikipedia articles would be unnecessarily confusing (who says "methanoic acid" instead of "formic acid") and unnecessarily bland. So my vote is for "propylene"—it's the name most chemists use, it's harder to confuse with "propane", it's the root of "polypropylene," etc. Yilloslime (t) 00:23, 24 April 2008 (UTC)

It should be propene, this name is very common and widely used (including chemists) in addition to being systematic and IUPAC-recommended (in contrast to methanoic acid). Propylene sounds very, very outdated, it is a name that mostly survives in trivial names of some reaction products of the compound. Сасусlе 03:58, 24 April 2008 (UTC)

It doesn't make too much difference to me, as long as we have consistent nomenclature for ethene/ethylene, propene/propylene, butene/butylene, isobutene/isobutylene, polypropene/polypropylene, etc. This issue has gone on for quite awhile (including above), without any clear resolution. Perhaps we can reach a consensus and put it into the chemistry manual of style. -- Ed (Edgar181) 17:08, 24 April 2008 (UTC)

Along the same lines, User:AssegaiAli has also recently moved methyl butyrate to "methyl butanoate". I have reverted the move (at least for now), because all the related articles are currently named as "butyrates". I have also invited him here to discuss these renamings. In my opinion, it is important to be consistent, so let's see if we can reach an agreement as a community, then apply that conesensus throughout the chemistry articles. Thanks. -- Ed (Edgar181) 13:39, 25 April 2008 (UTC)

This sort of thing really is a nightmare to deal with, and always will be, and consistency is always going to be a challenge. (Thank God for redirects!) Acetate is easy, and IUPAC supports it but butyrate is less so because many students - our main readership - will only have heard the word butanoate. A Google comparison still strongly favours butyrate (caveat below). But where does the cutoff come? Valerate still wins hands down on Google, yet, many newly minted chem graduates would (I suspect) still be unfamiliar with the word. What about caprylate? Even many practising chemists rarely use the word caprylate, yet it still wins out on Google. (This illustrates the problem with "consistency") Many of these traditional words spread out into the popular world in food additives, plasticisers, etc, and once there they will take many decades to be displaced (long after chemists have stopped using the word). I even had a boss who referred to muriatic acid, but I don't think many chemists know that name now (do YOU know what it is? I bet Wim does!).

Another is regional differences, and also differences between industrial vs academic/research vs academic/teaching chemists. There can be differences too between (say) inorganic chemists and organic chemists. (Physical chemists, meanwhile, only use one chemical). I have found in the US, for example, that people are more likely to talk about isopropyl alcohol, but in the UK isopropanol was more common in the labs I worked in (no one called it propan-2-ol!). This leads to problems where editor 1 says, "no one calls it lead dioxide any more" and editor 2 says "of course they do - who ever heard of lead(IV) oxide?"!

So we have to find a balance between traditional names and systematic names. If we always stuck with popularity (Google, etc) we would probably still be writing articles called flammable air instead of oxygen (OK, I exaggerate) - but certainly caprylate instead of octanoate (a bad thing IMHO). Yet at the same time we don't want to follow every IUPAC rule to the letter. I have always taken the view that if a compound has a well used systematic name (such as ethyl pentanoate instead of ethyl valerate), then we should go with the more systematic name, even if it is a little less popular on a Google search. However, if the systematic name is rarely used, we should stick with the usual name everyone will recognise. The problems come with (1) the borderline cases, such as iron(II) sulfate) vs ferrous sulfate, and (2) with cases where there are many names in use such as (tributyltin, tri-n-butyltin hydride (the name I hear most) or tributylstannane. As we revamp the chemistry style guide, we need to resolve this issue.

As for the propylene/propene issue, this is yet again a borderline case. As a teacher, I'd favour propene, but I wouldn't shed many tears if it was switched - I know that propylene is still popular in many industrial settings. Also, note that much of the higher Google rank for propylene (5 million vs 1 million) comes from pages about propylene oxide, propylene glycol and propylene carbonate. Looking at the tenth Google page, I noted that only two out of the ten hits were about CH3CH=CH2. (As Bullitt Darlington says, "Caveat Googletor"!) If you adjust for that ratio right across the 5 million, you would find that both propene and propylene would come out about 1 million each, and so I would go with 'propene. Walkerma (talk) 16:43, 25 April 2008 (UTC)

I don't think it is possible to be strictly consistent as the articles should reflect generally recognised preferences. In the case of ethene (which I admit I prefer), the article is best entitled ethylene because this name is universally recognised by experts and laymen and ethene is definitely only an lesser alternative. In the case of the other alkenes, this is less clear however, as the trivial names are falling out of use, largely because they are much more familiar to experts than they are to the layman. In their case I think the systematic name is the best one for the article. In extension, I feel that chemicals that well-known outside chemists' circles should be called by their most familiar names, while those that most people know very little about are more safely, IMHO, described by their systematic names. Overall, I think consistency is important, but communicating knowledge effectively is more so.--AssegaiAli (talk) 19:04, 25 April 2008 (UTC)

A mostly agree with everything that's been said above, and most with especially with the acknowledgment that prop(yl)ene is a tough one, since both names are used about equally. I'm new here, so forgive me this idea has already been floated and shot down, but what about deferring to widely recognized source for naming issues, like say, The Merck Index.? If the latest issue of the Index is listing n-C₇H₁₅COOH under "caprylic acid" rather than "octanoic acid", than so should we, etc.

This is not as clear as with ethylene; I think the longer the alkene the more esoteric the trivial name becomes, and this is a borderline case. I personally tend to call them ethylene and propene (they just seem easier to pronounce that way ;-). But most people have only heard of propylene as the monomer of polypropylene, and "polypropene" is almost never used, at least in my part of town. Therefore I think either name is fine, although I lean slightly toward propylene. Perhaps its a matter of choosing between the "academic" and the "industrial" name. Since this is a major industrial chemical, perhaps more weight should be given to the industrial (but I will never yield to muriatic acid! :-) --Itub (talk) 07:20, 27 April 2008 (UTC)

New articles

2-Phenethyl propionate, 3-Methylpyridine, Dimethyl fumarate and 1-Phenylethylamine--Stone (talk) 14:02, 26 April 2008 (UTC)

• Thanks. Rated for WP:Chem. Wim van Dorst (talk) 12:58, 1 May 2008 (UTC).

There are two different types of arrows in 3-Methylpyridine. Which ones should be used? 84.75.152.187 (talk) 21:03, 21 May 2008 (UTC)

Preferred IUPAC names

At some point (it is already more than two years behind schedule), IUPAC will be publishing the updated version of the "Blue Book", its recommendations on organic nomenclature. The major change is the introduction of "Preferred IUPAC Names" or "PINs": these will give a unique (preferred) name for an organic structure, although other names will continue to be recommended for 'general' nomenclature. For example, "ethanoic acid" will not become 'wrong', but "acetic acid" will be the preferred name. The draft recommendations are available here: note that they only apply to organic compounds, although there is a IUPAC project to extend the system to inorganic compounds [8], expect completion sometime during the current century!

I think it would be useful to include these names explicitly in the chemboxes, although it is obviously a large task. Given the general attention being given to chemical articles during the CASRN verification, it does not seem an impossible job. Should we start now, or should we wait for the recommendations to be formally published? Physchim62 (talk) 15:27, 26 April 2008 (UTC)

• Hi Physchim, don't let some procrastination by IUPAC hold you back to edit all 5000 chemicals articles ;-). But browsing the hefty doc a bit, I don't see indications that it'll all be different now, so I don't think it will have a big effect. E.g., the article is already called acetic acid. Wim van Dorst (talk) 19:50, 26 April 2008 (UTC).

I think that once the Validation Set is ready for deposition that it would be worth having someone with enough energy and passion taking a look at the IUPAC names and checking for consistency with IUPAC PNs. I can provide that SDF file to someone to check at that time. It is NOT yet ready I'm afraid...too many other distractions on my side at present.--ChemSpiderMan (talk) 03:02, 27 April 2008 (UTC)

New pages

• Oxotrichlorobis(triphenylphosphine)rhenium(V) the synthesis yields LiAl and HCl which is impossible, needs a check!
• 2,3-Dihydroxybenzoic acid, Manganese(II,III) oxide, Iron(II,III) oxide have no big problems.--Stone (talk) 07:25, 30 April 2008 (UTC)

• • Thanks. Rated for WP:Chem. Wim van Dorst (talk) 12:57, 1 May 2008 (UTC)

Manganese oxide

There are two pages Manganese oxide and Manganese Oxide, the former is a disambig page and seems OK but the latter is a redirect to Manganese dioxide. I think the second one should be deleted. Axiosaurus (talk) 09:30, 30 April 2008 (UTC)

Redirects are cheap, so I re-pointed Manganese Oxide → Manganese oxide. Will have to look through all the pages that link to either of those to see if their links should be adjusted to be specific manganese oxide chemical pages. DMacks (talk) 10:17, 30 April 2008 (UTC)

ThanksAxiosaurus (talk) 16:30, 30 April 2008 (UTC)

PNG to SVG

Hi all, anyone know of a simple way to convert from .png to .svg? Chemdraws saved as .png don't seem to come out too well on WP and [this] page indicates that they should be .svg? Happy May Day :) Freestyle-69 (talk) 01:41, 1 May 2008 (UTC)

OTOH, we've had discussions about using imagemaps (e.g., clicking on any structure in a reaction goes to that chemical's page) .I don't think WP imagemaps are compatible with svg because there is no "native" image size to establish the coordinates. DMacks (talk) 03:06, 1 May 2008 (UTC)

Actually, they are (try clicking on the enzyme or compound names). Fvasconcellos (t·c) 22:05, 9 May 2008 (UTC)

Hrm, not sure why it didn't work when I tried it a while ago, but I didn't try that hard--thanks for correcting me! DMacks (talk) 06:31, 11 May 2008 (UTC)

For anyone else interested, there is some info here from User:Slashme, kudos to him. Freestyle-69 (talk) 06:33, 15 May 2008 (UTC)

Benzamil

New article. Anybody has anything to add? --Rifleman 82 (talk) 18:34, 1 May 2008 (UTC)

The article misses the CAS number. 84.75.152.187 (talk) 20:59, 21 May 2008 (UTC)

Reassessment of the Start-Class group in the worklist

Hi all, just to let you know: I have re-assessed all articles in the Stub-Class group (no surprises), and also in the Start-Class group. Some thirty articles have been re-classified, approx half down to Stub and half up to B-Class. I hope that the overall progress score isn't affected too much. Wim van Dorst (talk) 14:35, 4 May 2008 (UTC).

• The weighted progress jumped up to 63.0%, but the work on the stubs regressed back to 92.4%. May I kindly suggest attention to these Stub articles? Some need just a little TLC (mostly an infusion of some chemistry) to reach an acceptable Start classification. Wim van Dorst (talk) 21:03, 4 May 2008 (UTC).

WP:Chem in C&E News

I just heard about this. The CAS/Wikipedia collaboration was mentioned in C&E News recently. If you are an ACS member you can see this here; if not, you can look at the March 17, 2008 paper issue, pages 42-43, if your library has it. Walkerma (talk) 18:02, 6 May 2008 (UTC)

Well it's nice that C&EN accepts Wikipedia as a source of chemical information. However, let us not forget that CAS still pretends that a user cannot find a CAS Registry Number(R) on its database and then add it to the relevant Wikipedia article. Such an attitude is illegal and antiscientific and, if CAS continues in this way, it will find itself in court one of these days. Wikipedia should have no part in giving cheap publicity to an organization whose values are so obviously opposed to the freedom of knowledge. Physchim62 (talk) 15:34, 8 May 2008 (UTC)

• It's a short announcement, only on page 43. A bit of windowdressing, as pointed out by PC. Nothing I got worked up about. Wim van Dorst (talk) 21:18, 11 May 2008 (UTC).

New articles

• Peroxybenzoic acid
• Styrene oxide

--Rifleman 82 (talk) 21:58, 8 May 2008 (UTC)

Is there any reason, why you don't have a special page where the new articles are listed? In de-WP we have that (see here) and I prefer it to having new articles posted on talk pages. --Leyo 18:36, 9 May 2008 (UTC)

There is a bot that categorizes new pages. New chemistry articles are automatically reported at User:AlexNewArtBot/ChemistrySearchResult. The bot is of course not perfect, and others get reported here too, which seems to work fine for bringing these articles to the attention of chemists. -- Ed (Edgar181) 19:41, 9 May 2008 (UTC)

OK, I did not know (or not remember) that bot generated page. --Leyo 21:59, 9 May 2008 (UTC)

• Actually, we do have a special page, where new articles and many other interesting subjects are brought to our attention: here. What's wrong with that? Wim van Dorst (talk) 21:21, 11 May 2008 (UTC).

Category:Drug pages needing a structure drawing, Category:Chemical pages needing a structure drawing

Can an admin please change the following in {{Drugbox}} and {{Chembox new}} (both protected and I don't have sufficient user rights) in order to avoid non-article pages to be categorised:

• <includeonly>[[Category:Drug pages needing a structure drawing]]</includeonly>

to

• {{#ifeq: {{NAMESPACE}} | {{ns:0}} | [[Category:Drug pages needing a structure drawing]] }}

and

• [[Category:Chemical pages needing a structure drawing]]

to

• {{#ifeq: {{NAMESPACE}} | {{ns:0}} | [[Category:Chemical pages needing a structure drawing]] }}

Thanks. --Leyo 22:34, 9 May 2008 (UTC)

Done. Great idea, by the way :) Fvasconcellos (t·c) 00:22, 10 May 2008 (UTC)

Benzalkonium chloride & Chembox

Just to double check - we're not having Chemboxes for mixtures such as Raney Nickel. What about mixtures such as in this article? --Rifleman 82 (talk) 18:52, 13 May 2008 (UTC)

For a mixture such as this, which has useful applications as a mixture, and for which there is plenty of chembox-appropriate data specific to the mixture, I don't see why we shouldn't have a chembox. -- Ed (Edgar181) 19:20, 13 May 2008 (UTC)

• Having a chembox when sufficient appropriate data can be given for a mixture is not a problem: you can apply the chembox template wherever this is useful (if relevant only partially). The wikiproject WP:Chem is about articles on chemicals substances, not about mixtures. Raney nickel is in the gray area, as is this Benzalkonium chloride. If I would be pure, I'd ditch them both, but oh-well, why not? So, they're both still in. Wim van Dorst (talk) 21:20, 13 May 2008 (UTC).

New articles - inorganics

The following are newish but not mentioned here before as far as I can see: Tin(II) sulfide, Manganese(II) sulfide, Bismuth(III) sulfide, Chromium(III) nitride, Mercury(I) iodide, Nickel(II) bromide, Bismuth trifluoride, Arsenic pentafluoride, Arsenic trifluoride.
--Axiosaurus (talk) 08:25, 17 May 2008 (UTC)

• I rated the ones that weren't rated yet, but didn't find anything particularly interesting, so they're all at Low importance and Stub or Start class. There isn't a rule that an article has to be listed here for being a formal chemicals article. Wim van Dorst (talk) 15:21, 18 May 2008 (UTC).
• Actually, you can find all new chemicals articles here. Wim van Dorst (talk) 20:57, 18 May 2008 (UTC).

Thanks - new to me - and a very useful page --Axiosaurus (talk) 08:37, 23 May 2008 (UTC)

Some kind of bromic acid

Hi. I was looking for the article on some kind of bromic acid with the formula O=Br-OH. As I don't know its name exactly, I could not find it. Can anyone help? 84.75.152.187 (talk) 20:56, 21 May 2008 (UTC)

In parallel with ClO_x^– naming, BrO₂^– would be "bromite", so HBrO₂ would be "bromous acid". DMacks (talk) 21:27, 21 May 2008 (UTC)

Could be. Unluckily, there is no article on bromous acid and not even a link to that substance (Special:WhatLinksHere/Bromous acid). 84.75.152.187 (talk) 23:01, 21 May 2008 (UTC)

I think the problem is not that the name "bromous acid" is incorrect, but rather that wikipedia just doesn't have an article on the chemical since it's not a very notable compound.Yilloslime (t) 23:47, 21 May 2008 (UTC)

As far as I know, bromous acid is unstable and decomposes to bromine and bromic acid. However, some of its salts are stable and bromous acid is supposed to be an intermediate in some interesting oscillating reactions, so it may be notable enough. --Itub (talk) 05:55, 22 May 2008 (UTC)

As far as I see, there is a structural formula of that substance on Commons. --Leyo 08:16, 22 May 2008 (UTC)

Yes, it is used in the German article[9]. If someone could translate it, that would be a good start. --Itub (talk) 09:41, 22 May 2008 (UTC)

For the linguistically challenged between us, I have created it as suggested by Itub. Wim van Dorst (talk) 22:06, 22 May 2008 (UTC).

Thanks. I added the structural formula. 84.75.152.187 (talk) 00:10, 23 May 2008 (UTC)

Chloroformic acid

The talk page of Chloroformic acid includes aurgent call for help with the article! So lets one or two things, for example that the stuff is related to phosgene --Stone (talk) 12:34, 22 May 2008 (UTC)

Benzenediazonium chloride

Benzenediazonium chloride has a large portion of the diazonium compound as content, and the name of the compound should be Phenyldiazonium chloride? --Stone (talk) 05:00, 23 May 2008 (UTC)

calcium(I) chloride

Does anyone have any information on this compound? It looks very deletable, (I haven't flagged it). It was reported in the 50's "Über das Calciummonochlorid, Ehrlich and Gentsch, Naturwissenschaften, (1953), doi:10.1007/BF00628837", but didn't find its way into Wells 3d edition 1963. Recently it has been stated that the compound does not exist, (Gerd Meyer, Dieter Naumann, Lars Wesemann 2007 Inorganic Chemistry in Focus III Wiley-VCH ISBN 3527609091). This is a bit like ditellurium decafluoride the difference being that Te₂F₁₀ probably seemed more believable at the time and hence was reported in textbooks.--Axiosaurus (talk) 09:40, 23 May 2008 (UTC)

It is possible that CaCl cannot be synthesized as a stable compound that you can put in a jar, and that the article is entirely wrong. But nevertheless, there are a couple hundred papers on CaCl. After a cursory inspection, I think most of them are gas phase experiments or calculations. Some have to do with astrophysics or astrochemistry, and at least one has to do with pyrotechnics (apparently you can find CaCl in a flame). So even if it turns out that the stable compound doesn't exist, it is at least possible to write an article about the gaseous CaCl (if someone really wants...). --11:33, 23 May 2008 (UTC)

We have plenty of articles about compounds which don't exist, see sulfurous acid or ven ammonium hydroxide for examples! Deletion is not the only solution: if we think the articxles might reappear (as in the two cases above), it is better to explain why we don't think that the compounds exist. In this way, we stop well-meaning editors from creatin a new article from scratch on said imaginary compound! Physchim62 (talk) 14:25, 23 May 2008 (UTC)

Hexafluorosilicic acid

User:Petergkeyes is hiding out at this article, re-adding unduly detailed safety (especially for such a short article) info despite pleas from me and Smokefoot not to do so (and several reverts). I think his work on the article has frustrated Smokefoot enough to make him take a leave of absence from WP.

Wear protective clothes and gloves when handling. If swallowed, rinse mouth. DO NOT induce vomiting. Store separate from strong bases, food and feedstuffs. Corrosive to eyes, skin, and respiratory tract. Corrosive upon ingestion. Inhalation of vapors may cause lung oedema. Symptoms of lung oedema may take several hours to appear, and may be exacerbated by physical exertion. Attacks glass and stoneware. May be hazardous to the environment, may harm aquatic organisms.

Two requests for you guys:

• Do we have a simple guideline on how much safety info to add? I read the relevant style guideline, but it's vague. I think we should draft on, quickly, if it doesn't already exist.

• Would anyone be prepared to persuade this editor to conform to our usual style a bit more? He seems to only edit fluoridation related articles, and only from a certain POV! I tried to reason with him, but obviously unsuccessfully.

Ben (talk) 06:07, 27 May 2008 (UTC)

Looks like User:Petergkeyes has over looked an even more dangerous hazard in drinking water, the rather scary - Dihydrogen monoxide, maybe we can get him to edit there? -- Quantockgoblin (talk) 08:13, 27 May 2008 (UTC)

The paragraph you quote is obviously against WP:NOTMANUAL. It is even written as imperative step-by-step instructions! It should be replaced by a short summary of the facts and refer the reader to more detailed articles such as fluoride toxicity and hydrogen fluoride. In fact, I've done that already.[10] If Petergkeyes keeps adding medical advice how to against policy, he should be warned (and if that doesn't work, blocked). --Itub (talk) 08:24, 27 May 2008 (UTC)

For more details about my opinion about how we should treat toxicity of "mildly toxic" substances, please see User talk:Itub#NaF_toxicity. --Itub (talk) 09:04, 27 May 2008 (UTC)

I left an extra message on the talkpage of Petergkeyes. These additions are indeed against WP:NOTMANUAL, and (for more dangerous compounds) may be also a problem of stuffing beans. --Dirk Beetstra ^{T C} 09:13, 27 May 2008 (UTC)

Comments on [11] and [12]? --Rifleman 82 (talk) 10:49, 27 May 2008 (UTC)

You say "the hazards associated with a chemical compound should ordinarily be described in the Chembox". I think the key question is the meaning of "ordinarily". I propose having a sort of "notability criterion" for toxicity. The criterion I have in mind has little correlation with LD50 or similar measures of toxicity; it is rather based on the available information about the mechanisms of toxicity and about actual cases of intoxications. Therefore, it depends heavily on the ubiquity of the substance in question. For example, we can very well have encyclopedic information about the "toxicity" of water and of sodium chloride (and indeed, we do!), because these are ubiquitous substances with many documented cases and known mechanisms. But we don't need a long exposition about the toxicity an obscure laboratory chemical for which all the available information is the MSDS. Sometimes, as in the case of dimethylmercury, one specific case with wide media attention can make its toxicity notable despite it being a relatively uncommon substance. In the case of hexafluorosilicic acid, I would say that there is little notability for its toxicity beyond the toxicity of hydrofluoric acid and perhaps fluorides and acids in general. So a brief mention with links to those articles should suffice. I'm not sure I agree with relegating this information entirely to the infobox, for usability reasons. The R- and S-phrases are little known and cryptic, so the reader might not notice them. A short (1-2 sentence) summary of the hazards in prose can be helpful, and does not need to be in a separate section (a short section invites people to expand it, which is not always I good idea). --Itub (talk) 11:39, 27 May 2008 (UTC)

Totally agree with you for H2SiF6. If you have the time, would you care to include your list at the style guidelines? --Rifleman 82 (talk) 12:11, 27 May 2008 (UTC)

That sounds good, I like the state of the article as it is now. The main problem was the step-by-step MSDS-style text and the way the editor concerned was using it to push a POV about fluoridation. Why is WP so full of quacks? I wish we could just block them at birth.

Ben (talk) 11:52, 27 May 2008 (UTC)

Ammonium perrhenate

I don't have institutional access to journals anymore. There's an article in Inorg. Synth. which presumably describes the laboratory preparation of this compound:

• Richard J. Thompson, Tung-Ch'Ing Wang, Jacob Kleinberg, George M. Adams, Burl E. Bryant. "Ammonium Perrhenate". Inorganic Syntheses. 8: 171–173. doi:10.1002/9780470132395.ch44.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Perhaps someone can read it and expand the article? --Rifleman 82 (talk) 06:31, 2 June 2008 (UTC)

Hmm, what do you want adding? The article seems correct to me, and probably contains most of the verifiable data we're going to find on this compound. I am not sure that it is "the form in which rhenium is most commonly traded"—such an assertion should really have a reference, and I have almost always acquired my rhenium as the metallic powder—but otherwise I don't see great problems. Physchim62 (talk) 14:00, 2 June 2008 (UTC)

I agree about the "commonly traded" bit - I used to get it usually as the sodium salt.

With regard to the preparation section. The cited source doesn't suggest if it is a lab scale process or not. If Inorg Synth says the same, then we can say that too (... this procedure is also usable in the laboratory[2]...) I've come across some documents which suggest that any general rhenium-containing material may be dissolved in base piranha and precipitated the same way, but I can't remember the reference. Perhaps this ref will state that too? --Rifleman 82 (talk) 15:14, 2 June 2008 (UTC)

Niobium monoxide

Should this be Niobium(II) oxide.--Stone (talk) 17:36, 10 June 2008 (UTC)

Probably, yes, depending on whether it is appropriate to give it an exception for common use of the name (which I doubt). Physchim62 (talk) 17:43, 10 June 2008 (UTC)

My use of the stoichiometric name was deliberate, as I reckon that as a predominantly materials science related chemical, it is better known as that. I have also created a page niobium dioxide for NbO₂. If you want to change the titles go ahead as long as there are redirects it won't matter.--Axiosaurus (talk) 13:27, 18 June 2008 (UTC)

Template fixed

Hi all, I think I fixed the problems with Comments in the {{chemicals}} templates. They should now be editable, readable, visible, nestable, etc. If not completely correct, please point it out: After more than a year with a broken template, I think it now needs our attention. Wim van Dorst (talk) 21:30, 11 June 2008 (UTC).

Proof-reading

Hey all. Although I'm not too active on WP with major edits, I'm very willing to proof-read articles and make changes wrt spelling, grammar, punctuation and sentence structure. So, if there are any articles out there that really need a good going over (or you've just done a major edit and don't wish to proof it yourself), drop me a note on my talk and I'll go through it. I do a reasonable bit of proof-reading in non-WP-land so it's pretty quick and easy for me. I'd prefer to stick to chem-related articles, so I haven't put myself on the main list of proof-readers. Cheers, Freestyle-69 (talk) 03:25, 15 June 2008 (UTC)

Template:Chem disclaimer up for deletion

The discussion is here: personally, I think the grounds for deletion are pretty strong, but I would like it to be done in an orderly manner and with discussion ;) Physchim62 (talk) 15:25, 16 June 2008 (UTC)

Nippoqualone

I have nominated the chemical article nippoqualone for deletion. Please feel free to weigh in at Wikipedia:Articles for deletion/Nippoqualone. -- Ed (Edgar181) 18:31, 17 June 2008 (UTC)

Good news, everyone!

There are no more redlinked halides at solubility table. (Not that I'm claiming we have an article on every inorganic halide, but it was a personal goal of mine, for some odd reason.) A list of the articles I've created is at User:Shoy. shoy 13:49, 20 June 2008 (UTC)

• Good work, Shoy! All Chemicals articles I assessed for mostly Stub/Low, but also several higher upto B/Mid! ps. There are still lots of other non-halides with red links in the table (hint). Wim van Dorst (talk) 21:58, 20 June 2008 (UTC).

Well, yeah, but you gotta start somewhere. :) shoy 20:44, 21 June 2008 (UTC)

Good! I'm very partial to metal halides myself! Thanks, Walkerma (talk) 06:22, 22 June 2008 (UTC)

This kind of partiality should always be taken with a pinch of salt, I think ;-). Wim van Dorst (talk) 23:01, 23 June 2008 (UTC).

On a side note, it's always cool when a robot adds an interwiki link to one of my articles, and I follow it to find that it's a translated copy of my article. (Those editors at de.wiki are fast!) shoy 23:54, 25 June 2008 (UTC)

Chemical data in chemboxes

As many of you know, we have a couple of databases (see article lists here and here), in which we are trying to check the key data - formula, molar mass, InChI/InChIKey where appropriate, CAS numbers (incl those from CAS). The project has hit a bit of an impasse lately, as we need to decide how to store the data on-wiki. There are two choices, and I'd like to get people's thoughts here. We will also meet on IRC at #wikichem on freenode on Tuesday, 1600h UTC to discuss this topic.

What we need is a way to present validated data in our chemboxes without the data being wide open to vandalism. We would also like these data to be findable by Google et al, on the article page. We need to be able to maintain and upload the data easily, and watch for any edits 24/7. There are two main ways (descriptions taken from the last IRC):

1. Use of {{InChI}}, which takes advantage of the Persondata system. The idea is to insert machine readable code at the end of each article which identifies the compound(s) discussed. ADV: is based on an accepted principle, is invisible to most users so less of a target for vandalism, links search engines etc directly to the article page. Works better that #2 when there are multiple compounds discussed in a single article: each one has its own template, and the average reader won't notice the difference; the bot reader, on the other hand, will know that each of the compounds is treated on that page. DIS: hardly looks very glorious for all the effort we're expending, difficult to expand to include more data than simple identifiers. May be hard for it to handle fields beyond the basic, such as structures. See test example (scroll to bottom of page).
2. The idea is to place the code for the Chembox on a subpage, which will then be transcluded (like a template) into the article. ADV: the chembox pages can be easily monitored for changes, and are less visible to passing vandals. DIS: it is more difficult for well-meaning users to add data to the chemboxes, WP in general does not like subpages for exactly this reason. See test example.

I think both could be used. Does anyone here have a preference? Walkerma (talk) 07:18, 22 June 2008 (UTC)

I don't suppose we could create a huge (perhaps xml based?) database containing all the contents of our chemboxes, and have each chembox pull the relevant entry? In effect, we'd create our own CRC hadnbook, fully sortable and searchable! --Rifleman 82 (talk) 14:19, 22 June 2008 (UTC)

As a side benefit, we can merge the (data page)s into this database, but only transclude a fixed set of parameters to avoid table creep. --Rifleman 82 (talk) 14:21, 22 June 2008 (UTC)

Another benefit would be allowing other wikis to pull our data, especially the numerical ones. Less wasted effort! --Rifleman 82 (talk) 14:59, 22 June 2008 (UTC)

Dirk, PC and others - is this sort of thing feasible? There are two issues involved - technical and political. The political include both "domestic" WP politics and also "international" (our relationship with outside groups such as CAS). I know CAS don't want a simple downloadable database of CAS numbers on the Web, we agreed not to distribute such a thing. Walkerma (talk) 14:45, 23 June 2008 (UTC)

I'm ambivalent about option 2. This is more or less the current practice for articles on chemical elements. I have several elements watchlisted, but I usually neglect watchlisting the infobox template. I'm afraid I'm not alone, because on several occasions I've seen misinformation creeping into these infoboxes and staying unreverted (presumably unnoticed) for months. However, option 2 might work if the monitoring is automated. --Itub (talk) 14:59, 23 June 2008 (UTC)

I'd planned to set up an alternate account that watchlisted all the data subpages. All the subpages would be in a category, so a bot could watch them for changes. Another advantage of the data subpage is that a bot could automatically sync them with whatever external database whenever said database was updated (also for initial uploading)...easier than having to insert that data into a full WP page. DMacks (talk) 15:24, 23 June 2008 (UTC)

I have made some changes to the on-IRC bot 'CheMoBot' (used for reporting changes to chemical pages). It has now, rudimentary, qualities to check changes to certain variables in all pages having a {{chembox new}}/{{proteinbox}}/{{drugbox}} (I have hard-coded some variables into the code, should do it with a database or on-wiki page). In principle it would be possible to check changes against a database. That would detect some vandalism, and not be too non-wiki (politically). If need be, we could even make the bot autorevert, but that may be taking it a step too far.

For now I would like some of our IRC-users to have IRC open when possible (not necesserily to chat, but to review every now and then what the bot 'says'). After some time (and some error-checking ..) we could discuss the possibilities of this. --Dirk Beetstra ^{T C} 16:14, 26 June 2008 (UTC)

I'm willing to hang around, but my online-time is rather fragmentary. Could you register an account for Chemobot and have it publish logs on wiki every say, 6 or 12 or 24 hours? --Rifleman 82 (talk) 16:28, 26 June 2008 (UTC)

(edit conflict) I was just about to ask the same thing! See this as an example. Walkerma (talk) 16:31, 26 June 2008 (UTC)

User:CheMoBot

I have claimed the on-wiki account CheMoBot (same name as the on-IRC bot). We could use this account later on for reporting/checking/repairing etc. (have to go through the usual requests, but I don't think that will be a problem). I started the userpage with a manual for the on-IRC part.

Next step would be to have somewhere on a subpage a database of handleable size and format, containing validated information. Xml would be a good format for me to read, but that also turns into a downloadable database of information then (something not all parties may agree with). Checking data against a verified (and protected) database should then be possible (and I could make the bot update the information). Someone familiar with the wiki-politics of having protected, validated information and making bots 'protecting' validated information? --Dirk Beetstra ^{T C} 11:23, 27 June 2008 (UTC)

Moved the settings to an on-wiki page (which may end up being fully protected in the end, when the bot is starting to run for real): User:CheMoBot/Settings. I am playing a bit with data on User:CheMoBot/Data, feel free to play a bit with that, but it may not be the final format for it! --Dirk Beetstra ^{T C} 10:24, 30 June 2008 (UTC)

The data-checking is working .. -ish (enough issues left). The bot now uses on-wiki lists (User:CheMoBot/Data and User:CheMoBot/Settings), but the format is awful, and there is not too much data yet. Feel free to play with it, and please add some data to check its working (but don't put too much effort in it yet). The bot only reports to IRC at the moment (if you are whitelisted, enter 'CheMoBot debug' otherwise it will not show your edits, use 'CheMoBot nodebug' to put it back in normal mode). 'CheMoBot help' for some more info. Have fun! --Dirk Beetstra ^{T C} 16:02, 30 June 2008 (UTC)

Forgot, you can use User:Beetstra/Propane for some testing, see User:CheMoBot/Settings for which fields the bot (should) recognise (and please add more fields/boxes to your own taste). --Dirk Beetstra ^{T C} 16:07, 30 June 2008 (UTC)

And I should add, don't worry about making mistakes, if something goes really wrong, the worst that can happen is that you will not be able to play anymore until I restart the bot. And then I probably know what I have to do to the bot to prevent it from happening again. --Dirk Beetstra ^{T C} 19:26, 30 June 2008 (UTC)

I have asked for approval to perform edits with this bot: Wikipedia:Bots/Requests for approval/CheMoBot. --Dirk Beetstra ^{T C} 14:41, 15 July 2008 (UTC)

I am manually putting the log in the appropriate subpages under Wikipedia:WikiProject Chemicals/Log (only for {{chembox new}} for the moment). I'd like to hear some comments (at the moment every single edit is logged, later when I have the 'level's proper, a template can be used to hide certain levels so it only shows e.g. link additions and similar). --Dirk Beetstra ^{T C} 13:24, 1 August 2008 (UTC)

Oh, I should add here: the bot assigns 'levels' to the 'severity' of the edit (at the moment between 0 and 5). Though not of real interest now, for later functions that may be of interest (say that we define 'vandalism' as 5 and we make the bot autorevert in the far future on level 5 .. leaving lower levels unaffected). I am now trying to tweak that a bit, but if there are comments on that, I'd like to hear that too. --Dirk Beetstra ^{T C} 13:52, 1 August 2008 (UTC)

The log gooks wonderful, and the level feature sounds great too! I'm just looking forward to the day when the bot will WRITE the articles for us, so we can wile away the hours on WP arguing over what font the atom labels should be for structures on data pages! Seriously, this is great work, and will help us in our attempts to reach a higher level of professionalism in chemistry. Walkerma (talk) 14:19, 1 August 2008 (UTC)

WORK :-)

I have coded the bot to write some of the boxes to disk, and I have copied a handful of them to subpages of Wikipedia:WikiProject Chemicals/Index.

As these are raw copies (and I saw some encoding problems here and there), I'd like to have some help in 'verifying' them. To start:

• Repair values which have wrong encoding (working on repairing that).
• Clear all fields of which the data is not (or can not) be verified.
• When verified, change the <status> in the template {{tlx|Status: <status> in each section to 'verified'.

I will use the current pages to test things, if you encounter strange things, or would like to see the bot add something somewhere in the section (in the preset comments), please leave me a message. --Dirk Beetstra ^{T C} 11:30, 4 August 2008 (UTC)

Some additions:

I am working on making the bot listen to 'keywords' as well.

• When a field is not known (but may exist), just leave it empty. But if you know that for a certain field the value simply does not exist (I would think of in the order of 'the refractive index of concrete' or 'the boiling point of concrete', then use the value '#NA' in the field.

If there are more of these typical things, then I can also generate 'keywords' for that. --Dirk Beetstra ^{T C} 12:33, 4 August 2008 (UTC)

Further:

• I have generated a handful of pages now, and am testing more. Please poke me on-IRC if you think that a certain compound needs to be done 'now' (e.g. the next FA), then I will provide the data for that (though you can always copy the data yourself, using the same format as the other index pages use).

Enjoy. --Dirk Beetstra ^{T C} 12:33, 4 August 2008 (UTC)

iron(II) chromate

We have a new article(?) on the above. The formula of this is FeCr₂O₄ and the article is based on the name in the List of CAS numbers by chemical compound. I would call this compound iron chromite, maybe iron(II) chromite. It needs renaming and the list correcting - but to which name? --Axiosaurus (talk) 20:46, 24 June 2008 (UTC)

Another option: merge it to Chromite? shoy 13:00, 25 June 2008 (UTC)

Of course it's a not a chromate. Many articles and much (most?) content are created by novices who don't know much chemistry but are determined to contibute recently acquired, still fragile knowledge. They're testing new found skills. So my policy with such editors, at least the registered ones, whom I admire, has been to assume good faith but also assume an almost complete absence of context, and, often, flimsy grasp of the facts. That's Wikipedia.--Smokefoot (talk) 13:40, 25 June 2008 (UTC)

I'd like to delete it for WP:CSD#A3 no content. What do you guys think? --Rifleman 82 (talk) 14:09, 25 June 2008 (UTC)

Sounds fine, unless someone finds can rescue it. After digging through Google books, I think that chromate of iron is an old synonym for the mineral chromite. But iron(II) chromate is a systematic name that does not fit chromite. Therefore it can be deleted unless someone can find anything to say about the real chromate, FeCrO₄. I'm not even sure that it can exist, having an oxidizing anion and a reducing cation on the same compound... --Itub (talk) 14:38, 25 June 2008 (UTC)

I originally wanted to rescue this article by finding something (anything!) to say - MSDS, etc. But no, nothing found online. Perhaps the list should be corrected, though. Anyhow, we shouldn't be referencing ourselves. --Rifleman 82 (talk) 14:43, 25 June 2008 (UTC)

FeCr2O4 is a spinel-structure double oxide, known as mineral chromite Eudialytos (talk) 14:47, 30 July 2008 (UTC)

Structure searching on Wikipedia

One of my dreams for WP:Chem imagines a day when a chemist can go online, draw a structure, then click "search Wikipedia" and get a relevant hit. The problem has always been that we don't have a way to draw structures on WP. ChemSpiderman and myself were chatting on the phone after IRC the other day, and realized that this may be possible, if the drawing script was off-wiki, but when you click search it performed a search on-wiki (using InChIs or InChIKeys (or maybe SMILES), behind the scenes). I suggested that ChemSpider could consider offering such a feature (it already has this type of search option internally). User:ChemSpiderMan believes this can be done quite easily, and he has put together a Powerpoint to explain his approach. He can email this to anyone who is interested. Is this a good idea? Are there any problems I've missed? Walkerma (talk) 06:54, 28 June 2008 (UTC)

The approach I am suggesting will also allow SUBSTRUCTURE searching of Wikipedia since when searched it will provide a list of substructure hits to Wikipedia via the search capabilities we will introduce. Doing full structure searches using InChIKeys and InChIstrings is obvious but in order to perform substructure searches the set will need to be indexed. --ChemSpiderMan (talk) 14:40, 29 June 2008 (UTC)

Denatonium structure pic

Is there an easy way to resize the benzoate half of the structure (they are separate pics) in the chembox? At the moment the dominant structure is the benzoate, which could be a bit confusing for some. Cheers, Freestyle-69 (talk) 01:43, 30 June 2008 (UTC)

I think Template:Chembox new/doc#Extra images has the trick you want. DMacks (talk) 01:53, 30 June 2008 (UTC)

Thanks! Done. Freestyle-69 (talk) 02:20, 30 June 2008 (UTC)

C Class

A user has changed many classifications of articles in the scope of the WikiProject Chemicals from Start class to C-class. Here are their contributions: Special:Contributions/Nergaal. I am under the impression that there is no C-Class in the assessment scale for Chemicals related articles. Am I correct in thinking this or should we allow this user to continue to change the assessment class of practically every chemical page in wikipedia? See [Diff] for the response from the user. I am not sure who is correct. Jdrewitt (talk) 15:39, 30 June 2008 (UTC)

Template:Grading scheme. Also, the articles you are tallking about are within the scope Wikipedia:WikiProject Elements moreso than they do to the Chemicals one. I was assesing them based only on the requirements of that project. Nergaal (talk) 15:45, 30 June 2008 (UTC)

Even so, I would appreciate someone else's opinion.Jdrewitt (talk) 15:47, 30 June 2008 (UTC)

The C class was approved by a general vote at Wikipedia talk:Version 1.0 Editorial Team/Assessment, but there are still some issues under discussion there. While I don't think what Nergaal is doing is completely wrong, I think it is premature. I would rather wait for the general discussion to settle a bit, and have at least some discussion here announcing the new class before starting to change the ratings. The ratings may need some "localization" to each wikiproject, updates to the templates, examples, etc. --Itub (talk) 15:49, 30 June 2008 (UTC)

I think changing the templates prior to re-assessment is key here, since although the articles fall within the scope of Wikipedia:WikiProject Elements, the template messages on these article talk pages point to an assessment scale which does not currently acknowledge the C-Class. Jdrewitt (talk) 16:23, 30 June 2008 (UTC)

Why isn't the assesment scale the same or parallel to the one used by WP 1.0 Editorial Team? Especially since the present one is made when the version was 0.5? (i.e. the thext now is "This article has also been selected for the Version 0.5 release of Wikipedia.") Nergaal (talk) 17:54, 30 June 2008 (UTC)

I've been coordinating this transition at the 1.0 team; we need to discuss how the new class will affect B-Class in particular. Unfortunately I'm away at a conference, but when I get back we'll resolve things and contact WikiProjects (I'm aiming for an official announcement on Friday). A few projects have already begun to do C-Class assessments anyway. I wouldn't worry about reverting assessments, unless the project feels that we should reject the use of C-Class altogether. Walkerma (talk) 03:55, 1 July 2008 (UTC)

This is going to be an interesting discussion, but as I'm due to leave tomorrow morning early, I can't provide more than my vision: The C-Class it totally unnecessary for the Wikiproject Chemicals. Since a few days, we have over 5000 articles in our wikiproject, and as an assessor (I guess I've assessed some 1500-2000 in the last months), it is my sure opinion that we do very well without newfangled C-Class or GA-Class, thank you. Our historic set of assessment rules (they are the origin of the general wikipedia assesment rule, for the new editors reading this) need not be adjusted because other projects need more precise assessment. Note also, that our assessment is against completion of the chemical content of the article, so an article can well be classed B-Class in some wikiproject (e.g. Biology) and still be a Stub in our wikiproject. So there is no requirement for all wikiprojects' assessment to be equal, on the contrary. I'm off now: happy vacationing to all of you. Wim van Dorst (talk) 21:28, 1 July 2008 (UTC).

Articles flagged for cleanup

Currently, 1368 of the articles assigned to this project, or 27.3%, are flagged for cleanup of some sort. (Data as of 18 June 2008.) Are you interested in finding out more? I am offering to generate cleanup to-do lists on a project or work group level. See User:B. Wolterding/Cleanup listings for details. Subsribing is easy - just add a template to your project page. If you want to respond to this canned message, please do so at my user talk page. --B. Wolterding (talk) 17:20, 3 July 2008 (UTC)

I think we should go with this. Although I think cleanup tags are sometimes used rather randomly, I'd certainly like to see what are our worst offenders. Walkerma (talk) 06:07, 4 July 2008 (UTC)

Rifleman took care of it. shoy 13:55, 4 July 2008 (UTC)

Changes to the WP:1.0 assessment scheme

As you may have heard, we at the Wikipedia 1.0 Editorial Team recently made some changes to the assessment scale, including the addition of a new level. The new description is available at WP:ASSESS.

• The new C-Class represents articles that are beyond the basic Start-Class, but which need additional references or cleanup to meet the standards for B-Class.
• The criteria for B-Class have been tightened up with the addition of a rubric, and are now more in line with the stricter standards already used at some projects.
• A-Class article reviews will now need more than one person, as described here.

Each WikiProject should already have a new C-Class category at Category:C-Class_articles. If your project elects not to use the new level, you can simply delete your WikiProject's C-Class category and clarify any amendments on your project's assessment/discussion pages. The bot is already finding and listing C-Class articles.

Please leave a message with us if you have any queries regarding the introduction of the revised scheme. This scheme should allow the team to start producing offline selections for your project and the wider community within the next year. Thanks for using the Wikipedia 1.0 scheme! For the 1.0 Editorial Team, §hepBot (Disable) 21:32, 4 July 2008 (UTC)

Potassium hydroxide

It's tagged for clean up; I assume it referred to the huge list of "uses". I've trimmed off most of the vague descriptions. If you guys have the time, you can take a look at it? --Rifleman 82 (talk) 01:40, 5 July 2008 (UTC)

PAH Template

Do we have a template for Polycyclic aromatic hydrocarbons (like Template:Cycloalkanes, etc)? I couldn't find one. The reason I ask is that Phenalene (not Phenylene) showed up at WP:RA/NS. It kind of surprised me that we didn't have one, and I feel it would help facilitate the filling in of the missing article(s). I'd create one myself, but I don't know a lot about template creation or where a good list of PAHs can be found. shoy (reactions) 13:44, 10 July 2008 (UTC)

I have created Template:PAHs and added compounds from Category:Polycyclic aromatic hydrocarbons which I thought were important. Feel free to add/subtract from it as you see fit. -- Ed (Edgar181) 16:36, 22 July 2008 (UTC)

Is indene really considered a PAH? I always assumed that all rings had to be aromatic. --Itub (talk) 17:19, 22 July 2008 (UTC)

It is polycyclic and it has aromaticity and it is a hydrocarbon, but you may be right; because each ring is not aromatic, maybe it shouldn't be considered a PAH. I won't object if you remove them. -- Ed (Edgar181) 17:24, 22 July 2008 (UTC)

I see that you took care of phenalene as well. Much thanks, Edgar. shoy (reactions) 20:36, 22 July 2008 (UTC)

You're welcome. It's just a stub and certainly could use more content though. -- Ed (Edgar181) 21:00, 22 July 2008 (UTC)

Isn't isoindene nonaromatic?

Ben (talk) 20:49, 22 July 2008 (UTC)

D'oh! You're right. Isoindene definitely shouldn't be there. I removed indene for now, too. -- Ed (Edgar181)

Cinnarizine

The article on cinnarizine states that it is not available in North America. It is however listed as having Rx and OTC versions on Canadian mail-order sites, and the OTC is shipped from India in blister packaging with the brand name Stugeron on the package. —Preceding unsigned comment added by Rxdoxx (talk • contribs) 01:39, 16 July 2008 (UTC)

I've copied this comment to Wikipedia talk:WikiProject Pharmacology where it might be more relevant. -- Ed (Edgar181) 13:48, 16 July 2008 (UTC)

Stannic acid

Is the structural formula in the German article correct? If yes, it should be moved to Commons and used in the article. 84.75.159.26 (talk) 08:07, 16 July 2008 (UTC)

The English article says that stannic acid is Sn(OH)₄, but the German article says H₂SnO₃. That inconsistency should be sorted out. Both chemical formulas represent hydrated forms of SnO₂, and all three may interconvert depending on temperature, humidity, storage conditions, etc. In any case, Chemical Abstracts names "stannic acid" as a synonym for H₂SnO₃ (CAS#13472-47-4, structure the same as given in the German article). -- Ed (Edgar181) 13:44, 16 July 2008 (UTC)

So it should be correct then, isn't it? Did you find it on a Chemical Abstracts site that is available to the public so it could be used as a reference? 84.75.159.26 (talk) 11:25, 19 July 2008 (UTC)

It looks like the English article should be corrected, but I had hoped that someone with more inorganic chemistry experience could weigh in. Chemical Abstracts is not a public service (access to it should be available from any good university library, though) but it can still be used as a reference anyway where necessary. -- Ed (Edgar181) 12:34, 19 July 2008 (UTC)

My recommendation would be to convert the article to a redirect and note in the tin dioxide article that hydrated SnO₂ is sometimes called "stannic acid." This kind of article has been problematic for years here - silicic acid and titanic acids are labels for similarly vaguely defined materials. The naming seems archaic, predating modern structural chemistry. Because, however, hydrated oxides are often commercially useful or naturally occurring, the nomenclature is well entrenched especially in environmental and industrial realms. With regards to the H₂SnO₃ vs Sn(OH)₄ issue, the specific question is whether stannic acid is associated with a specific stoichiometry (mono or dihydrated SnO₂, or is it a mix of oligomers) and the sepearate, less important, cultural issue about how that stoichiometry should be represented (e.g. H₂SO₄ vs SO₂(OH)₂). So, unless I hear howling or alternative suggestions, I am considering converting the article to a redirect and preserving some of the nuggets of information in the targeted article.--Smokefoot (talk) 13:04, 19 July 2008 (UTC)

I have just returned from an unscheduled wiki break--I agree with smokefoot- articles about hypothetical acids such as stannic are a real problem- the so-called stannic acid is typical and probably less well characterised than most. There is a commercially available "stannic" aka metastannic acid, which is (approximately)the monohydrate in stoichiometry. As for structure- I can't find a definitive statement, however the german articles "classical" structure is almost certainly incorrect for the solid phase. The only problem I see with redirecting as per Smokefoots suggestion is that the stannic article will then reappear at some later date. As for nuggets in the existing article- there aren't many IMHO as it doesn't square with Greenwood and Wiberg. I will add some information when the decision is made.--Axiosaurus (talk) 13:30, 19 July 2008 (UTC)

Copper(I) sulfide

Copper(I) sulfide is quite a good overview article about the many copper sulfide binary compounds, but has comparatively little about copper(I) sulfide. There is additionally a disambig page, copper sulfide pointing to copper(I) sulfide and copper(II) sulfide. I propose that the content of the copper(I) sulfide page is moved across to the disambig page which would become a summary page for all the various Cu_xS_y phases and a new page is created for copper(I) sulfide which can then be developed with a chembox etc.--Axiosaurus (talk) 10:15, 20 July 2008 (UTC)

Copper(II) sulfide is mistitled since CuS is mixed-valence consisting of both Cu(I) and Cu(II) sites as well as counterbalancing S^2- and S₂^2-. So in this sense its title copper(II) sulfide is incorrect and might be relabeled, converting copper(II) sulfide to a redirect.--Smokefoot (talk) 13:42, 20 July 2008 (UTC)

Tantalum hafnium carbide

What is this empty box for? 84.75.159.26 (talk) 00:02, 22 July 2008 (UTC)

It is patiently waiting to be filled with data. -- Ed (Edgar181) 12:36, 22 July 2008 (UTC)

ChemSpider ID

I'd like to revisit the issue of ChemSpider ID in our chemboxes. Discussion is here. --Rifleman 82 (talk) 18:15, 22 July 2008 (UTC)

Fluoridation

I write to invite chemically educated editors to put the various fluoride sources on their watch list as these articles are targets by those that are passionate about their opposition to water fluoridation. Three articles have been created within Wikipedia that address this controversy - fluoride poisoning, water fluoridation controversy, dental fluorosis. These articles are largely written by antifluoridation-advocates and, ironically for this reason, these articles may lack the very plausibility that these advocates seek. Most chemical editors cede these controversy articles to the advocates. As a practical matter, it is difficult to squeak in a balancing comment. So my advice or plea is that we chemical editors strive to keep the pure chemical articles soberly focused on the chemical, per se. This applies most to sodium fluoride, hexafluorosilicic acid, but stannous fluoride, fluoroapatite, sodium monofluorophosphate, and other articles are likely targets. The advocates usual strategy is, borrowing from the intelligent design and creationist communities, to request that we "teach the controversy," i.e. that there are diverse views on the advisability of fluoridating public drinking water. We already have three articles teaching this controversy.--Smokefoot (talk) 13:25, 23 July 2008 (UTC)

Clairol (chemical)‎

I have nominated Clairol (chemical)‎ for deletion. Please feel free to contribute to the discussion at Wikipedia:Articles for deletion/Clairol (chemical). -- Ed (Edgar181) 20:04, 23 July 2008 (UTC)

Adding information on the natural (mineral) occurence of chemical compounds

Hello to all the wiki-people! I'm new here, however a time ago I've started uploading information about natural occurences of some chemical compounds. It was already told in a letter send to me, that its possibly not good/important/needed to put up the names of minerals which are very rare.

I would like to kindly ask about this rules... In my personal opinion, even such informations (on rare minerals) could i.e. make some people interested in mineralogy. The more, some minerals that were taken as rare before, now can be found more often, mainly due to new analyzing techniques, like EPMA and SEM-EDS systems. Alos, the minerals that are extremely rare are often very complex and some people even don't use to call them chemicals. This includes the minerals of eudialyte group (-;

I have also some question about just putting informations on wikipedia. I'm a mineralogist interested in systematic mineralogy and some informations that I put are just remembered by me, however sometimes I brace with few mineralogical sites. Generally, the informations I (would like to) put are commonly found in most of mineralogical books, sites etc. I would like to ask if its ok to put such informations here? (I mean additional sentences on already existing pages as well new articles).

I would be thankful for any answers (-:

Thank You!

Best regards to all!

Luke K. Eudialytos (talk) 10:18, 24 July 2008 (UTC)

Well, welcome: we rely on folks with technical insight and enthusiasm, and the absence of a political agenda. The key question is "notability". Many extremely esoteric factoids describe our world, so use your judgement. As a practical matter, it is impossible to state every truth about every chemical, so be prepared to occasionally defend the notability of your information. One alternative approach would be to develop articles on classes of rare minerals.--Smokefoot (talk) 13:31, 24 July 2008 (UTC)

Thank You! I'll try to do my best (-: In my opinion it is good to look for 'bridging' different sciences (-: By the classess of rare minerals You've meant articles on its classification or rather single minerals short descriptions? Greetings! Eudialytos (talk) 14:10, 24 July 2008 (UTC)

Hydrochloric acid FAR

Hydrochloric acid has been nominated for a featured article review. Articles are typically reviewed for two weeks. Please leave your comments and help us to return the article to featured quality. If concerns are not addressed during the review period, articles are moved onto the Featured Article Removal Candidates list for a further period, where editors may declare "Keep" or "Remove" the article from featured status. The instructions for the review process are here. Reviewers' concerns are here. Nishkid64 _{(Make articles, not wikidrama)} 13:39, 24 July 2008 (UTC)

Pentylamine

Could someone provide a little context for Pentylamine? I'd hate to delete an article I just created a structure for :) Fvasconcellos (t·c) 14:59, 25 July 2008 (UTC)

It is used as a solvent, [13] maybe that helps. --Itub (talk) 15:15, 25 July 2008 (UTC)

It does indeed. Thanks! Fvasconcellos (t·c) 15:30, 2 August 2008 (UTC)

"New pages"

Created a "new pages" subpage (Wikipedia:WikiProject_Chemicals/New_pages) for editors who write new articles to list them. Purely voluntary, but some editors might want to follow changes by RSS (http://en.wikipedia.org/enwiki/w/index.php?title=Wikipedia:WikiProject_Chemicals/New_pages&feed=rss&action=history). New articles typically start out as stubs, so listing them here might encourage further development.

Since our articles are free for infinite reuse, listing them here will allow other websites (e.g. Tony's chemspider) create links into WP. This applies for any other database out there. This is conceptually no different from Wikipedia:Database download. --Rifleman 82 (talk) 03:47, 29 July 2008 (UTC)

Oh, I just found Wikipedia:Version_1.0_Editorial_Team/Chemicals_articles_by_quality_log. This is so much easier and better. --Rifleman 82 (talk) 03:56, 29 July 2008 (UTC)

A link to that subpage might be added on the top of this page somewhere, so it can be found easier (after that this section would be archived). --Leyo 08:44, 29 July 2008 (UTC)

Top of WP:chemicals [14]. --Rifleman 82 (talk) 08:57, 29 July 2008 (UTC)

There is also this page: User:AlexNewArtBot/ChemistrySearchResult. -- Ed (Edgar181) 20:53, 29 July 2008 (UTC)

Thanks, Ed. I saw it earlier, but AlexNewArtBot seems a bit crude, with a bit many false positives. I just looked at it in detail... maybe a bit of bug reporting will help. --Rifleman 82 (talk) 01:12, 30 July 2008 (UTC)

I think the two lists complement each other well, because the first one depends on having the wikiproject template in the talk page and also logs changes in ratings, whereas the second one finds actual new articles that may be relevant, even if they don't have the template. --Itub (talk) 04:52, 30 July 2008 (UTC)

Titanium boride

This page discusses about TiB2 (titanium diboride), yet the page is listed as Titanium boride, is this an error? Thanks, Marasama (talk) 15:43, 30 July 2008 (UTC)

The name given to a compound is the "common name". There are a number of Ti/B phases- Ti₂B, TiB, TiB₂ and the Ti₂B₅. What I suggest we do is to rename the TiB₂ article to titanium diboride which is often used ,and make titanium boride a disambiguation page referring to the various known phases, see manganese oxide as an example of what I mean.--Axiosaurus (talk) 08:17, 1 August 2008 (UTC)

WP:CHEMSTYLE for Reactions

Does anyone know why the Chemstyle guidelines say that reactions that are not in-line should not be done in LaTex but instead in HTML? Personally, I think the Latex helps them stand out and helps readability and writability. EagleFalconn (talk) 16:31, 1 August 2008 (UTC)

Wikipedia:Manual_of_Style_(chemistry)/draft#Reactions is a draft guideline. Wikipedia:WikiProject_Chemicals/Style_guidelines#Chemical_reactions is the existing. --Rifleman 82 (talk) 16:39, 1 August 2008 (UTC)

I disagree with the notion that the change in font size is 'jarring.' Pop open a gen chem book if you have one around, reactions that are a focus of the text are always displayed prominently and easy to find. On the other hand, on Wikipedia placing reactions in HTML form between two line breaks for a reaction that you wish to make prominent just makes it hard to find. Especially in an article like Acid dissociation constant (the one that makes me ask the question) where there is a lot of math (leading to use of LaTeX). The result is that the math stands out quite well, but it becomes hard to find the chemical reaction the math is referring to. Besides, no one ever goes to a math article and tells them to use HTML instead of LaTeX because the font size change is 'jarring.' EagleFalconn (talk) 16:54, 1 August 2008 (UTC)

Oppose LaTex. I find alternative fonts unwelcome because, although the proposal is clearly well-intentioned, more complex formating is a mechanism by which style trumps content. The evolving philosophy on these pages has been to maintain low barriers to make this project inviting to chem-savvy editors, at the expense of some glitz.--Smokefoot (talk) 17:22, 1 August 2008 (UTC)

The problem with LaTeX is that the font used is with serifs, and it is italicised. This makes it very inconsistent with the text. On the other hand, in mathematics, alphabetical characters are expected to be in italics anyway. If a complex formula is required, the best solution is always to draw it out as an image, anyway. I don't have a general chemistry text, but the few journal articles I have on this computer, as well as the free-access OrgSynth (e.g. [15]) articles I have do not have bigger and italicised text for reactions.--Rifleman 82 (talk) 17:26, 1 August 2008 (UTC)

It is possible to force letters to be upright (roman) in LaTeX, but it is time-consuming and looks formidable to anyone trying to edit the code.

See, for example, Wikibooks:A-level Chemistry/OCR (Salters)/Equilibrium constants.

Ben (talk) 17:58, 1 August 2008 (UTC)

I do appreciate the problem of keeping low barriers to editing -- It took me a little time to figure out how to read LaTeX and figure out some of the HTML stuff as well. But there has got to be some kind of middle ground that keeps articles readable. A majority of my reason for wanting this change is because any article that has math and reactions is going to look ugly -- there has got to be a way to solve the font size change and the italics problem. Is there any way we could create a <chem> tag similar to the math tag that would essentially be LaTeX but no italics and a smaller font size? EagleFalconn (talk) 18:04, 1 August 2008 (UTC)

I've taken a look at the acid dissociation constant page, and I see his point. I think this is one of the rare cases where elemental symbols and mathematical notation need to coexist, thus the problem. --Rifleman 82 (talk) 18:18, 1 August 2008 (UTC)

• phew* I'm glad I'm not just a rambling nutjob. I have no problem with not using LaTeX in-line, I agree that HTML belongs there. But the objection to using LaTeX not in line is a little specious to me, even in articles that don't have math. I'll keep my objection, for now, to articles with math to expedite the discussion because acid dissociation constant is very quickly about to come up for Class A review and then WP:FAC, and I'd like to figure this out soon so the article doesn't look wonky. EagleFalconn (talk) 18:31, 1 August 2008 (UTC)

I don't see the problem with using normal text for reactions and LaTeX for mathematical equations. But we should edit the maths so that element symbols are upright. All you have to do is write \mbox{X} to make the text X upright.

$NH_{3}\,\!$	${\mbox{NH}}_{3}\,\!$
<math> NH_3 \,\!</math>	<math> \mbox{NH}_3 \,\!</math>

Ben (talk) 18:35, 1 August 2008 (UTC)

The issue isn't with the format itself -- the issue is what happens in the context of an article that uses both. If you write down a chemical reaction and then a couple lines down have a mathematical equation associated with that reaction, if they are different sizes/styles the article becomes awkward to read. Also, I don't really see the issue with chemicals being italicized or not. I don't think anyone reading an article that is clearly chemical in nature is going to confuse "HA" for two variables multiplied together. Heck, I'd never even noticed that LaTeX italicized by default until it was pointed out here. I really feel like this whole distinction is a non-issue. I almost want to call it a WikiIssue -- something you only notice when you're so close to the Wiki that you lose a little perspective. EagleFalconn (talk) 18:43, 1 August 2008 (UTC)

I quote from acid dissociation constant, "thermodynamics" section, just below the table containg delH and TdelS:

$CH_{3}C(O)O-H+OH_{2}\rightarrow CH_{3}CO_{2}^{-}+H-OH_{2}^{+}$

This is exactly why we shouldn't use LaTeX for chemical equations. --Rifleman 82 (talk) 04:14, 2 August 2008 (UTC)

The appropriate markup, IMHO:

CH₃COOH + H₂O → CH₃COO⁻ + H₃O⁺

--Rifleman 82 (talk) 04:18, 2 August 2008 (UTC)

I don't see how thats a problem with LaTeX itself instead of a failure of the author of the reaction (which I thought I'd fixed earlier today...) to change it to

$CH_{3}CO_{2}-H+OH_{2}\rightarrow CH_{3}CO_{2}^{-}+H_{3}O^{+}$

Seriously. The only difference between my statement and yours is font size and some easily resolvable stylistic differences between how to write reactions. For the record, I am not the person who wrote that reaction into the article but I support it as I've written in this comment. EagleFalconn (talk) 05:11, 2 August 2008 (UTC)

I'm not blaming you personally for that line. Just pointing out the deficiencies. In any case, the amended version still doesn't look "right". The line between "CO₂-H" is not a minus sign, it is a single bond. It should not have spaces to the left and right of it. The superscript minus sign adjacent to -CO₂^- on the RHS of the equation should not be directly above the subscript 2. For example, SO₄²⁻. End of the day, LaTeX is designed to write mathematical, not chemical equations. I don't see why we should jump through hoops to make it work with chemistry when that is not what it was designed to do. --Rifleman 82 (talk) 06:02, 2 August 2008 (UTC)

Haber_process shows the use of both styles at the same time. IMO the chemical equations at the section "Synthesis gas production" look perfectly fine, as does the equation for the equilibrium constant of the reaction. Taken as a whole, the article is okay. So, I still feel strongly that chemical equations should be written in HTML; if it is too complex to be written in HTML, it should be drawn out, e.g.:

If the use of mathematical notation is necessary, such as in the writing out the equilibrium constant, etc., then by all means, use LaTeX. --Rifleman 82 (talk) 06:08, 2 August 2008 (UTC)

I support that usage (HTML for chemistry, LaTeX for maths - even if the maths includes chemical formulae). I don't think it looks awkward at all. What does look awkward (and is awkward to write) is LaTeX for chemical reactions.

Ben (talk) 11:32, 2 August 2008 (UTC)

This issue must be resolved

What all you critics of inline LaTeX are missing is the simple fact that ⇌ for the equilibrium sign is barely legible as (LaTeX) $\rightleftharpoons$, which it is supposed to represent. This single issue needs to be resolved now, not the general one of in-line LaTeX. I have some 40 years' experience of University teaching in chemistry and I have NEVER seen an equilibrium sign as pathetic as ⇌ in any text-book or other publication. In this instance legibility must come first because the specific unicode character, 8652, or any other single character for that matter, is inadequate and illegible. Petergans (talk) 19:34, 2 August 2008 (UTC)

Looks fine in my browser. But I remember a while ago lots of people complained about this unicode symbol being misrendered by their browser. The LaTeX version is legible but ugly.

Ben (talk) 20:44, 2 August 2008 (UTC)

Looks perfectly fine in Win/FF2 and 3.FF3 Looks a bit small in IE, but still legible. --Rifleman 82 (talk) 05:25, 3 August 2008 (UTC)

Yawn.--Smokefoot (talk) 21:14, 2 August 2008 (UTC)

To get an impression how chemical equations can look like using LaTeX you might want to take a look at the german wikipedias guidelines here. It's the standard of formatting equations in a seperate line on de-wp. --NEUROtiker (talk) 21:58, 2 August 2008 (UTC)

P.S.: The spaces beneath the minus sign as single bond can be easily avoided this way:

<math>\mathrm{H_3C{-}COOH}</math>

$\mathrm {H_{3}C{-}COOH\ }$

If you don't like Fonts with serifs there are also fonts without:

${\mathsf {H_{3}C{-}COOH\ }}$

So we now all have to learn LaTeX? please keep it simple, if you can use HTML/WikiFormat, please do (play a bit with the size if the ⇌ is too small:

2 H₂O ⇌ H₃O⁺ + OH^-

). If it then gets too difficult for that, then switching to LaTeX may be a plan. --Dirk Beetstra ^{T C} 10:26, 6 August 2008 (UTC)

I don't like using Latex in Wikipedia unless there is a really compelling reason (such as equations with integrals), but I agree with Petergans that the Unicode arrow looks pathetic (not so bad in Benjah's system, but in the Windows and in Linux systems I use it is tiny). I think the current approach in Acid dissociation constant looks reasonable enough: Latex is only being used for the arrows themselves, while the rest of the chemical equation is HTML. --Itub (talk) 11:03, 6 August 2008 (UTC)

Dacemazine

We have plenty of articles on obscure chemicals and drugs, and I was considering adding one more to the pile, dacemazine, a phenothiazine listed in {{Antihistamines}} under an old trade name. It's listed in PubChem, ChemFinder, and some medical literature from the 1950s, has a published rINN, and is apparently available commercially—but it was never marketed as a standalone drug and doesn't seem to be used anymore. I'm not keen on creating a "permastub", but... what do you folks think? Is this enough? Fvasconcellos (t·c) 15:30, 2 August 2008 (UTC)

Carlos Banez has been hard at work at that, so what's one more? I would support that you go ahead and start the new article. --Rifleman 82 (talk) 15:56, 2 August 2008 (UTC)

It appears Meodipt has gone ahead and created it :) Thanks for the input. Fvasconcellos (t·c) 14:04, 3 August 2008 (UTC)

Discussion about the symbol for liter at the Manual of Style

Should liter use the symbol L, or l? You may remember there was a discussion about it on this wikiproject earlier this year (Wikipedia:WikiProject Chemicals/archive05#Multiple_symbols_for_a_single_unit), which ended up with having the chemicals style guidelines treating it as variety of English issue. Now there is a more general discussion and a poll at Wikipedia talk:Manual of Style (dates and numbers)#Straw_poll_on_unit_symbol_usage_for_the_liter. --Itub (talk) 11:04, 4 August 2008 (UTC)

Proposed change to Template:Chembox CASNo

I've always wondered why we put brackets around the CAS numbers in Template:chembox new. Then I was looking at Alclofenac, and saw its CAS No. is a link to MeSH (the Alclofenac page uses Template:Drugbox). I like that better. So I poked around, and built some clone templates in my user space, and made a working version of Chembox CASNo that makes MeSH links. My version of the template is User:JaGa/Sandbox/CASNo, and here's the sandbox page I used for testing: User:JaGa/Sandbox/chemtest. Feel free to edit it for your own testing. If people like the idea, all we'd have to do is copy from User:JaGa/Sandbox/CASNo to Template:Chembox CASNo. --JaGa (talk) 02:53, 6 August 2008 (UTC)

"Square brackets around numbers" was always the traditional way to show CAS nos. in print, from the time they appeared (1967?). That's why I always write them that way, because I think it's clearer that it's a CAS no. and not a PubChemID or something. Why is it a problem? (I agree, though, that the metadata need to be searchable, but that doesn't preclude use of [], does it?) Walkerma (talk) 03:27, 6 August 2008 (UTC)

Well, it's not so much I have a problem with brackets as I'd like to make the data presented in a useful manner. I think clicking on a PubChem number and getting to the corresponding page is great; I like the idea of making the data clickable whenever possible. Also, we could put brackets around the CAS Nos in the template, keep with tradition, no problem. --JaGa (talk) 06:38, 6 August 2008 (UTC)

The square brackets do not preclude linking. We have had links in the past, but decided not to do it anymore as (most) external databases are not always correct (CAS numbers are not always properly defined, though people here have been working hard on that). Another problem is that the link should go to CAS, not to any other organisation, IMHO (MeSH goes to MeSH, ChEBI links to ChEBI, etc.). CAS does not provide this possibility, unfortunately. Hope this explains. --Dirk Beetstra ^{T C} 09:43, 6 August 2008 (UTC)

I agree that we shouldn't link the CAS numbers anywhere. If some database provides useful information about a chemical, it can be linked on its own right, but the CAS number has nothing to do with it. --Itub (talk) 10:29, 6 August 2008 (UTC)

Note: this is not an example of what I would call useful information. It just provides the name and the registry number. We already have that and much more in our infobox. --Itub (talk) 10:31, 6 August 2008 (UTC)

True, not a lot of info, but it does include a link to the MeSH. Many, many chemical pages do not have the MeSH link - or the PubChem link - so it would be useful in those cases. Should we be so quick to deny an opportunity to add information to the infobox? If a better link comes up - or CAS opens - we could always change the template again. I don't see the harm in it, and I do see where it would be useful. --JaGa (talk) 18:09, 6 August 2008 (UTC)

There's been a lot of work going on with the validation of chemical structures and associated CAS numbers and other identifiers. The time will come where we will have validated CAS numbers and non-validated CAS numbers. However I agree they should not be linked out to anything since they could be misassociated on the linked site. The CAS number can be listed but not linked IMO.--ChemSpiderMan (talk) 13:14, 6 August 2008 (UTC)

What about a special page such as Special:BookSources (example), where the entries of a specific CAS number in multiple databases are linked and can accessed directly? --Leyo 16:56, 6 August 2008 (UTC)

That would be very cool IMO. I would help setting it up if we want to go that way. --JaGa (talk) 18:11, 6 August 2008 (UTC)

This has been done once; see Wikipedia:Chemical sources? I don't recall what discussion led to links to this page being removed from chemical articles, though. -- Ed (Edgar181) 18:21, 6 August 2008 (UTC)

Great, we could use this as a springboard to make a CAS-specific search page, per Leyo's suggestion. Thoughts? --JaGa (talk) 23:10, 6 August 2008 (UTC)

JaGa, I am sorry to disappoint you, but the extension for that is available. The thing is, getting it activated on Wikimedia, they are not keen on specialised special pages (and I understand why). But when the specialised chembox came up, we did not persue this issue further (seems to be getting nowhere in the end). For CAS specific one of the issues is that the different suppliers use different CAS numbers and some compounds have more than one CAS, etc. etc. We now have a list of verified CAS numbers which would make the system less error prone, but still it will lead to difficult cases. CAS should link to CAS (especially since they have (and preserve) the rights on the number), and they do not provide a useful service for that, so I think we should leave it at that. ISBN is more open, the organisation behind it allows such searches. It might be good for other identifiers (PubChem, EINECS, InChI, SMILES, ...) which don't have such problems, and where 'owners' don't complain about this. --Dirk Beetstra ^{T C} 15:01, 2 September 2008 (UTC)

I met with some CAS people at the ACS meeting in Philadelphia, and they are considering the possibility of having open pages for the compounds they provided us with. It would only be a simple page - CAS#, name and structural representation, but this would be a great step forward, because it would provide evidence of validation from "the horse's mouth." They agreed (naturally!) that the best source for a CAS # is CAS! I think that within a year this is quite a reasonable possibility. However, for compounds that fall outside the validated set of ~4000, there will still be no link available, as far as I know. Walkerma (talk) 15:42, 2 September 2008 (UTC)

Perchlorates on Mars

The news that mars is full of perchlorates might get a lot of people wonder, and they will end up here to get informations, so we should improve the three places where the people will look. This is the:

• Perchlorate article which is good, but it needs improvment in the natural production section also the natural occurence here on earth should be made clear
• Mars the chapter soil already states that the toxic perchlorates will be problematic for the mission of NASA to grow aspargus on Mars, which is strange and needs work.
• Phoenix (spacecraft) here the MECA instrument was responsible for the findings. I have to read the article on MECA again, but I think they were not very happy with the perchlorate sensor, because the calibration substance for this sensor interfered with several others and they said: It is too late, but we should have replaced it with a sulfate sensor. They have been lucky not to have dne this.

I would be glad to have some help!--Stone (talk) 07:21, 7 August 2008 (UTC)

Hi! No natural (mineral) occurence of any chlorate or perchlorate was confirmed from Earth (or Mars) (the perchlorate article has been uploaded). In my personal opinion it would rather be strange if the Mars was full of perchlorates, unless there had been very strong oxidation sources existing there. From the other side, huge amounts of iron on Mars is present as Fe₂O₃, hematite. However, it is not 'difficult for the nature' to oxidize iron into such form. Oxidizing of chlorides (according to the article given above, detected on Mars but in small amounts) would be much more 'difficult'. The more, augite, which is mentioned as possible constituent of some Martian rocks, contains both bi- and trivalent Fe. According to article on perchlorate NASA mentioned occurence of (per)chlorates on Atacama. The place is indeed full of 'highly oxidated' minerals, like natural iodates(V), but no mineral with anions containing the central atom on (VII) state were found anywhere till now. Single potassium perrhenate grain(s) is mentioned from the Moon regolith, but not confirmed as single mineral species. Eudialytos (talk) 14:00, 15 August 2008 (UTC)

You mean updated? uploaded.

The oxidation of the chloride occures in the atmosphere and is a process involving oxygen and UV radiation. Oxygen and UV radiation is available in the higer atmosphere of mars. Perchlorate is stable in contact with ironII and ironIII, if you imagine the absence of liquid water and temperatures below 0°C. but no mineral with anions containing the central atom on (VII) state were found anywhere till now for this I would like to see a reference, because I have plenty of references saying that perchlorates can be found in some aride areas.

• Clayton W. Trumpolt, Michael Crain, Geoffrey D. Cullison, Susan J. P. Flanagan, Lenny Siegel, Stephen Lathrop (2005). "Perchlorate: Sources, uses, and occurrences in the environment". Remediation Journal. 16 (1): 65–89. doi:10.1002/rem.20071.{{cite journal}}: CS1 maint: multiple names: authors list (link)
• Purnendu K. Dasgupta, P. Kalyani Martinelango, W. Andrew Jackson, Todd A. Anderson, Kang Tian, Richard W. Tock, and Srinath Rajagopalan (2005). "The Origin of Naturally Occurring Perchlorate: The Role of Atmospheric Processes". Environ. Sci. Technol. 39 (6): 1569–1575. doi:10.1021/es048612x.{{cite journal}}: CS1 maint: multiple names: authors list (link)
• E. T. Urbansky, S. K. Brown, M. L. Magnuson and C. A. Kelty (2001). "Perchlorate levels in samples of sodium nitrate fertilizer derived from Chilean caliche". Environmental Pollution. 112 (3): 299–302. doi:10.1016/S0269-7491(00)00132-9.{{cite journal}}: CS1 maint: multiple names: authors list (link)
• Ioana G. Petrisor (2006). "Focus on Perchlorate". Environmental Forensics. 7 (1): 1–3. doi:10.1080/15275920500506659.
• William E. Motzer a; Thomas K. G. Mohr b; Sally McCraven a; Phyllis Stanin a (2006). "Stable and Other Isotope Techniques for Perchlorate Source Identification". Environmental Forensics. 7 (1): 89–100. doi:10.1080/15275920500506964.{{cite journal}}: CS1 maint: multiple names: authors list (link)--Stone (talk) 20:38, 17 August 2008 (UTC)

I've meant there's no single MINERAL SPECIES approved by the International Mineralogical Association (IMA) and its Commission on New Minerals and Mineral Names (CNMMN). This means that there's NO CONFIRMED SINGLE MINERAL containing any structural site, that is occupied in more than 50% by any chlorate anion. However, I'm sure its possible for some (i.e. nitrate or iodate minerals, like brüggenite or lautarite) minerals to have some structural sites partially occupied by ClO₃^- anion. Chlorine is present in Atacama minerals as Cl^- anion, like in schwartzembergite H₂Pb₅I³⁺O₆Cl₃ (as we can see, iodine can occur in such environment even in quite reduced form, but it occurs there mainly as IO₃^- anions, like in mentioned brüggenite or lautarite). So, the best reference is the actual mineral list published by International Mineralogical Association. Eudialytos (talk) 15:37, 18 September 2008 (UTC)

Naming of organic ligand- help /advice please

I came across this in Science, Stable Magnesium(I) Compounds with Mg-Mg Bonds doi:10.1126/science.1150856. Mg-Mg bonds sadly interest me and a new oxidation state for Mg deserves a mention. These guys have made a complex with an (Mg-Mg)²⁺ unit in it- with a number of bulky anionic ligands to stabilise it, LMg₂L. The best picture is here [16]- the aryl group is 2,6-diisopropylphenyl. What would the ligand be named. Alternatively if it is felt that the ligand name is too complex for a title - the article could possibly be named something like Mg(I) adduct or Mg(I) complexes --Axiosaurus (talk) 16:18, 9 August 2008 (UTC)

N,N'-(pentane-2,4-diylidene)bis(2,6-diisopropylaniline)?

The authors call it nacnac. See also http://dx.doi.org/10.1107/S1600536807043978 ("nacnac" = pentane-2,4-diiminato).

Ben (talk) 21:44, 9 August 2008 (UTC)

So, Axio's compound should probably be named bis[N,N'-bis(2,6-dimethylphenyl)pentane-2,4-diiminato]dimagnesium(I)? --Rifleman 82 (talk) 22:41, 9 August 2008 (UTC)

I know that's what I'd put into the search box ;) shoy (reactions) 00:52, 10 August 2008 (UTC)

Everyone in the business calls these types of ligands NacNac. (A La "acac" for acetylacetonate.) Having said that, I'd vote for "low valent Magnesium compounds" as the title, and discuss all molecular Mg compounds in +1 or lower oxidation states in that one article. If I recall correctly, the authors of that science report actually discuss a couple (very closely related) low valent Mg compounds in that article, and it'd be easiest to discuss them all in the same place rather than separately. Yilloslime (t) 01:22, 10 August 2008 (UTC)

See nacnac. Y'slime's suggestion is a good one.--Smokefoot (talk) 01:45, 10 August 2008 (UTC)

thanks everyone- I wasn't even close to getting the name! There may be the germ of an idea for a minority interest quiz show "Name that compound". I will go with Yiloslime's suggestion--Axiosaurus (talk) 10:08, 10 August 2008 (UTC)

Very interesting topic. I just added Mg(I) to the list of oxidation states of the elements; if you know of any other unusual oxidation states that are missing from the list, please add them or let me know. --Itub (talk) 14:48, 12 August 2008 (UTC)

Many of us have heard or given this rant multiple times, but here goes anyway: chemists love oxidation states and classification systems. Given intermetallics, non-stoichiometric compounds, nanosized clusters, the concept of oxidation state is treacherous. Yes, Mg(I) exists in things with Mg-Mg bonds, the same way that trivalent carbon exists in ethane, Mn(I) in Mn₂(CO)₁₀ and who-knows-what in boron hydrides and Cs₁₁O₃, etc. So are these fractional oxidation states to be listed also?--Smokefoot (talk) 17:26, 12 August 2008 (UTC)

No, the fractional oxidation states are excluded from the scope of the list, as mentioned in the lead (most fractional oxidation states are the average of several atoms with integer oxidation states anyway). This list was based on Greenwood's, and that's good enough for me. --Itub (talk) 17:39, 12 August 2008 (UTC)

BTW, Mn₂(CO)₁₀ has Mn(0)... sure, it is a formality, but so what? --Itub (talk) 17:42, 12 August 2008 (UTC)

Proflavine, need help.

Reading an AJ paper, I found that "Proflavine absorbs strongly in the blue region at 445nm (in water at PH7) with molar extinction coefficient of c. 40,000". I added that to the page, but am uncertain the exact way to make the page flow. And I am familiar that it is a spectrograph of the chemical, but uncertain after that. Thanks, Marasama (talk) 21:18, 13 August 2008 (UTC)

Final say on stereochemistry?

I was looking to replace Image:D-fructose-2,6-bisphosphate wpmp.png with Image:Fructose 2,6-bisphosphate.svg and noticed they don't jive on stereochemistry. To figure out who is right, I went to the PubChem article, (and it does mention "D-Fructose 2,6-bisphosphate" as a synonym) and saw its drawing matches the SVG, but the IUPAC and Isomeric SMILES disagree with the drawing - specifically, the -C-Phosphate group off of the ring is shown extending away from the viewer, but the stereochemistry data says the drawing should have that group in the plane, with a H extending away. So what do I trust for a definitive answer? --JaGa^talk 18:28, 18 August 2008 (UTC)

You could say they are both correct, because the name is incomplete--it doesn't specify which anomer. --Itub (talk) 22:40, 18 August 2008 (UTC)

Of course, it is likely that only one of the anomers is the one of biochemical interest. I don't know which, but I'd suggest checking a few biochemistry textbooks. --Itub (talk) 22:44, 18 August 2008 (UTC)

Having a current shortage of biochem textbooks lying around, I search Google Scholar and got this, which confirms the image as the one of interest, so I'll go with that. I was surprised - I expected the image to be "wrong" and the data accurate, but it seems the opposite. --JaGa^talk 04:25, 19 August 2008 (UTC)

G2ZT?

I wanted to put data/an SVG in the G2ZT article but can't find anything online about it. Could someone figure out what this is? The chembox is empty. --JaGa^talk 05:50, 25 August 2008 (UTC)

Search for Klapötke and 5,5-Azotetrazolate he is the guy from munich university, his lab does work with such nice compounds like hydrazinium azide or uranium hexaazide.Stone (talk) 09:02, 25 August 2008 (UTC)

It is the salt of 3,4,5-triamino-1,2,4-triazoleium (a five membered ring with 3 nitrogens at 1,2,4 position and the amine groups at the two carbons 3 and 5 and at the 4 nitrogen between) and and 5,5'-Azo-tetrazole ( two five membered rings with one carbon each, the two rings are bridged over a azo group -N=N-).{{doi|10.1002/prep.200500022}},doi:10.1002/1099-0682(200203)2002:4<834::AID-EJIC834>3.0.CO;2-Q--Stone (talk) 09:14, 25 August 2008 (UTC)

The CAS registry number is 1025740-53-7. --Itub (talk) 09:15, 25 August 2008 (UTC)

New article: Dichlorprop

Dichlorprop mistakenly redirected to 2,4-D, so I made a new article about Dichlorprop itself. Input is very welcome. Yilloslime (t) 16:39, 28 August 2008 (UTC)

Verified data for User:CheMoBot

I'll re-poke this discussion (there is an older thread above). The BRFA (bot request) found the solution using revids of pages for the 'storage' of verified data in infoboxes the best method. For that we now have 2 index pages, one for the {{chembox new}}, and one for {{drugbox}}:

• {{chembox new}} -> Wikipedia:WikiProject Chemicals/Index
• {{drugbox}} -> Wikipedia:WikiProject Pharmacology/Index

Both contain a few sample entries, but now the big task is coming: verifying the pages and getting them into the indices. What needs to be done for that:

• Find a page which is not yet in the index
• Check all fields on that page, especially the ones named in '<boxname>_fields' (the watched fields) in User:CheMoBot/Settings, i.e.:
  • for {{chembox new}}: C|H|N|O|P|Cl|Br|I|B|IUPACName|CASNo|EINECS|PubChem|SMILES|InChI|RTECS|MeSHName|ChEBI|KEGG|Formula|MolarMass|Density|MeltingPt|MeltingPtC|MeltingPtK|MeltingPtF|BoilingPt|BoilingPtC|BoilingPtK|BoilingPtF
  • for {{drugbox}}: molecular_weight|CAS_number|DrugBank|ATC_prefix|ATC_suffix|ATC_supplemental
  • (other fields can be added if wanted, it should have the fields for which hardly an argument is possible)
• Remove all data which can not be verified (especially in the 'watched' fields); add <!-- NA --> in fields which simply do not exist (e.g. the refractive index of a non-transparent material).
• Find the revid containing the checked version (see instructions on the Index page).
• Add a line to the index (Wikipedia:WikiProject Chemicals/Index or Wikipedia:WikiProject Pharmacology/Index) in the format described.
• (move on to the next page ..).

The bot now only compares the data/change of data with the box in the older revid of the page, and logs these changes. It is not a huge problem if there are some wrong values in there, but the majority should be right. If a page gives too many problems, ignore it and move on. The bot 'ignores' pages which have not a verified revid in the index, as well as fields which don't have a value in the infobox.

The indexes can be edited by anyone, and if a newer version of a page contains more verified data, then the index should be updated (it also means we need to keep an eye on it, as 'vandalism' on these pages will also have effects on the working of the bot ..

I really would like to get some help here, getting verified revids of the pages would improve the reliability of the encyclopedia, and when there is enough verified data (and we are confident that there are not too many mistakes), we may even consider using the bot to protect the verified data! Poke me (here, on my talkpage, or on IRC) when you have questions. Thanks! --Dirk Beetstra ^{T C} 16:13, 2 September 2008 (UTC)

I would ask that people ONLY USE VALIDATED DATA FROM THE CENTRAL RDF FILE that we were collaborating on. These have been checked by at least two people, against independent sources. We need first to upload the revids from Antony's "first 500" - how should we organize that? Walkerma (talk) 16:23, 2 September 2008 (UTC)

(note: This post is also on Wikipedia:WikiProject Pharmacology). That is fine, but indeed, then those 500 need to be checked against that, revids corrected and implemented in the index .. I don't think it can be done automatically .. at least not easy. --Dirk Beetstra ^{T C} 16:46, 2 September 2008 (UTC)

Walkerma, where is this central RDF file? --JaGa^talk 18:16, 3 September 2008 (UTC)

JaGa, sorry I missed your note but thankfully you now have the file. As per this week's IRC, I have created a page Wikipedia:WikiProject Chemicals/Chembox validation where we can coordinate the work of uploading the validated data. We will start with the first 500, which ChemSpiderMan distributed on May 12th. Hopefully Dmacks can upload a list of those articles on-wiki, but the actual validated data exist off-wiki. Please sign up to help check our data! Walkerma (talk) 07:19, 11 September 2008 (UTC)

DDT

At 93kb long DDT is a candidate for being split into sibling articles. Also, being a notable chemical with contentious issues surrounding its use, a number of articles can be created from the parent. Logical choices are History of DDT, Environmental impact of DDT, Effects of DDT on human health and DDT use against malaria (these are currently redirect pages due to a revert of my attempt to split the dDDT article). See Talk:DDT for my previous attempts at doing this and the opposition to it. -- Alan Liefting (talk) - 23:19, 2 September 2008 (UTC)

Santonin

I just gave santonin a chembox. I think the "chemical composition and derivation" section is wrong. For one, it is a lactone, not an anhydride. I took a look at santonic acid (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=283654) in pubchem, to try to figure out how it is the hydrolysis product. However, the pubchem structure seems out of this world. I can't fix it today. Maybe you guys can take a look? --Rifleman 82 (talk) 16:12, 4 September 2008 (UTC)

The structure given by Chemical Abstracts matches the one at PubChem. It appears to be an "anhydride" in the very broad sense that the molecular formulas differ by H₂O; but unless I'm really missing something, you can't get one from the other in any simple dehydration process. I've gone ahead and removed the statement, but if anyone can rewrite it more clearly and add it back in, please feel free. -- Ed (Edgar181) 16:58, 4 September 2008 (UTC)

santonic acid

Here's a hopefully better representation of santonic acid. While the net difference is indeed H2O, I wouldn't call santonin an anhydride, because it brings to mind a rather specific functional group. --Itub (talk) 17:13, 4 September 2008 (UTC)

This page has a nicer picture and shows the mechanism: [17]. --Itub (talk) 17:32, 4 September 2008 (UTC)

Very interesting. So, santonic acid is in fact a dehydration hydrolysis product of santonin, via a based-catalyzed multistep rearrangement process. I'll put the statement back in, specifying this. -- Ed (Edgar181)

Wikipedia 0.7 articles have been selected for WPChem worklist

Wikipedia 0.7 is a collection of English Wikipedia articles due to be released on DVD, and available for free download, later this year. The Wikipedia:Version 1.0 Editorial Team has made an automated selection of articles for Version 0.7.

We would like to ask you to review the articles selected from this project. These were chosen from the articles with this project's talk page tag, based on the rated importance and quality. If there are any specific articles that should be removed, please let us know at Wikipedia talk:Version 0.7. You can also nominate additional articles for release, following the procedure at Wikipedia:Release Version Nominations.

A list of selected articles with cleanup tags, sorted by project, is available. The list is automatically updated each hour when it is loaded. Please try to fix any urgent problems in the selected articles. A team of copyeditors has agreed to help with copyediting requests, although you should try to fix simple issues on your own if possible.

We would also appreciate your help in identifying the version of each article that you think we should use, to help avoid vandalism or POV issues. These versions can be recorded at this project's subpage of User:SelectionBot/0.7. We are planning to release the selection for the holiday season, so we ask you to select the revisions before October 20. At that time, we will use an automatic process to identify which version of each article to release, if no version has been manually selected. Thanks! For the Wikipedia 1.0 Editorial team, SelectionBot 22:27, 15 September 2008 (UTC)

Wikipedia 0.7 articles have been selected for Chemicals

Wikipedia 0.7 is a collection of English Wikipedia articles due to be released on DVD, and available for free download, later this year. The Wikipedia:Version 1.0 Editorial Team has made an automated selection of articles for Version 0.7.

We would like to ask you to review the articles selected from this project. These were chosen from the articles with this project's talk page tag, based on the rated importance and quality. If there are any specific articles that should be removed, please let us know at Wikipedia talk:Version 0.7. You can also nominate additional articles for release, following the procedure at Wikipedia:Release Version Nominations.

A list of selected articles with cleanup tags, sorted by project, is available. The list is automatically updated each hour when it is loaded. Please try to fix any urgent problems in the selected articles. A team of copyeditors has agreed to help with copyediting requests, although you should try to fix simple issues on your own if possible.

We would also appreciate your help in identifying the version of each article that you think we should use, to help avoid vandalism or POV issues. These versions can be recorded at this project's subpage of User:SelectionBot/0.7. We are planning to release the selection for the holiday season, so we ask you to select the revisions before October 20. At that time, we will use an automatic process to identify which version of each article to release, if no version has been manually selected. Thanks! For the Wikipedia 1.0 Editorial team, SelectionBot 23:05, 15 September 2008 (UTC)

Structural images standard?

Is there some type of standard (i.e. the preferred method of doing things) when it comes to images of molecular structures? I mean, is it standard to use (pure) bond line notation (a.k.a. skeletal formula), or mixed notation? Or is it just a free-for-all where any given image might use any variation/combination of different notations?

To be truly "encyclopedic", in the sense of accessibility, Wikipedia must present information in a consistent, coherent, and logical form. (This is why we have templates. More generally, in order to communicate anything at all, we need common definitions of terms, i.e. mutually accepted pattern repetitions. Conversely... Imagine reading a book that used different fonts, writing styles, and overall organizations on each and every page. It would be harder to read simply because of stylistic incoherence.)

My basic thinking is that encyclopedia articles are meant to follow a certain template, as if they were all sections of a book (or a series of books, as was the case prior to Wikipedia) with the same layout. This makes articles of the same class appear related, whether by common navigation bar templates, or by consistent writing styles.

(See articles in for an example of high organizational/writing consistency. Every article begins by describing some basic trait held in common with other, in this case the biological effects of a drug. provides the reader with a sense that all the compounds in the benzodiazepine family are related through common traits, though each trait is present in greater or lesser degrees in each member of the family. I digress.)

As far as molecular structure images go, there doesn't seem to be any sort of standard notation. I prefer a form of mixed notation that shows charges and avoids writing abbreviated functional groups (e.g. the -NO₂ group of the image of imidacloprid; rather than showing the group as NO₂).

Basically what I'm saying here is: if there isn't a "standard notation" for the molecular structure images found in Wikipedia articles... then there should be.

(Please notify me of responses to this post on my talk page, as I do not check this page regularly.)

Cheers, Fuzzform (talk) 03:44, 16 September 2008 (UTC)

I suppose we could encourage a default preference, but the use of abbreviations should always be at the discretion of the "artist". Sometimes abbreviations are necessary due to space constraints (think of NO2 in certain explosives), and sometimes the expanded version is necessary to emphasize points of structure and mechanism. In the specific case of NO2 I generally prefer the abbreviated version for simplicity (the alternatives could be misleading or unfamiliar to some readers). --Itub (talk) 06:40, 16 September 2008 (UTC)

Wikipedia:WikiProject_Chemistry/Structure_drawing --Rifleman 82 (talk) 07:45, 16 September 2008 (UTC)

Bumping up priority for BPA article

Dear chem gurus,

You all are doing amazing work, and are surely overworked.

There was a lead article in the Journal of the American Medical Association today that gave strong indications from a human study of large health risk increases associated with levels of exposure to the plastic Bisphenol A, commonly known as BPA, that are under those rated "safe" by the FDA and EPA. As a result of this finding, I would ask that you bump up the priority of revising this article's contents, which is currently rated only "Medium" importance.

Please see the discussion tab for that page for its holes. In particular, there is a notable deficit of advice in the article on how consumers can better gauge the composition of common household plastics, including unlabeled (non 1-7) plastics.

Thanks for your attention and heroic efforts! A.k.a. (talk) 02:23, 17 September 2008 (UTC)

I raised this to High, which I think is the right level. I heard a radio interview this evening with someone involved with the story. Based on its large-scale usage only, this was already borderline High, but the recent Canadian ban and other public scrutiny makes it that more definite. Thanks for pointing it out. Walkerma (talk) 04:49, 17 September 2008 (UTC)

BioDME

New article has sprung up. I've listed a few concerns at Talk:BioDME. Perhaps you guys can take a look? --Rifleman 82 (talk) 16:14, 18 September 2008 (UTC)

Add DDT to the worklist?

Can we have DDT added to the worklist at Wikipedia:WikiProject Chemicals/Organization? It is a long article, an important chemical, and there is differences of opinion about how it should be edited. See Talk:DDT. -- Alan Liefting (talk) - 03:58, 19 September 2008 (UTC)

A silly question, perhaps: does anyone actually use the worklist for anything? I often use the importance categories (Category:Chemicals articles by importance) but I've never use the worklist. I find the category system more dynamic and comprehensive. Am I alone, or is the worklist just a historical artifact? --Itub (talk) 05:29, 19 September 2008 (UTC)

Agree with Itub. Can we just mark it historical and retire it? --Rifleman 82 (talk) 05:39, 19 September 2008 (UTC)

Being a sort of dinosaur, I actually see the list as a group of core articles of the Chemicals wikiproject. These 382 articles on chemicals compounds, out of the 5000+ in wikipedia, have been selected because they are important themselves, or representative of a certain class of chemicals. As such, I still think that the worklist has an important value. Not as a list of classifications (we do that differently nowadays), but as the list of WP:Chem articles that we should give our prime attention to. That is what we agreed on in the start of the WP:Chem (see here). So I do agree that the list could do with some copy-editing (removing the partially outdated ratings), but I don't agree with any archiving or removal proposal. And not to additions either, btw, to avoid goal creep. Wim van Dorst (talk) 20:19, 24 September 2008 (UTC).

Polythiazyl, (SN)_x

Flicking through Greenwood & Earnshaw, it seems that polythiazyl, (SN)_x, is quite an interesting and important compound that has attracted a great deal of attention from researchers.

Our article is currently rather poor - a short stub without references and very little discussion. I've stuck in a reference to a comprehensive review article, but I don't know a great deal about (SN)_x. I'll read about it and add what I can. Would anyone else care to join in?

Ben (talk) 13:01, 21 September 2008 (UTC)

(SN)_x is a fascinating species that time has passed by, it was, as they say, "a material for the future and always will be". The area of conductive polymer, organic electronics, and some of the specific materials (polypyrrole, polyacetylene etc) is dominated by PProctor, who has waged a multi-year, one-person campaign to voice his embitterment over what-I-am-guesing is his thesis advisor's (John McGinness) missing (not even mentioned in) a Nobel that went to Hideki Shirakawa et al for polyacetylene. I tried to edit in this space to expand scope or to tone down the sour grapes theme, but gave up (BTW, PProctor has also been active in Nobel_Prize_controversies, especially over the MRI Nobel). SN_x is mentioned in tetrasulfur tetranitride, from which it is derived. We dont have many editors in the molecular materials area.--Smokefoot (talk) 14:57, 21 September 2008 (UTC)

We can't let whole topics get hijacked by individuals with an agenda. I'll do what I can to polythiazyl, and if PProctor or anyone else gets in the way of improving this article, please will an admin deal with them robustly (e.g. block).

Ben (talk) 16:00, 21 September 2008 (UTC)

Benzoin condensation

Has been a term that's annoyed me- it's not a condensation as there's no loss of a small molecule (typically water). Is this one of those cases where the common term prevails? If so, I think a comment is required to dispel this misnomer. Any thoughts? I'll do it, but not if I've overlooked something obvious. Freestyle-69 (talk) 06:52, 23 September 2008 (UTC)

I think it's "just one of those things that's entrenched." There actually is a comment about this naming issue buried in the text. But while we're there, whoa nelly does the chemistry on that page need an overhaul! Uses "asymmetric" to mean "mixed" (not stereoinduction), mechanisms illustrate proton motion but call it the reaction mechanism, says cyanide is the specific catalyst but then says thiamine can do it too (and it's a common undergrad experiment to use thiamine for benzaldehyde), says that alpha-nitrile position is acidic only due to inductive effect. DMacks (talk) 07:20, 23 September 2008 (UTC)

Even IUPAC acknowledges this "entrenched usage" in its Glossary of terms used in physical organic chemistry: "The term is sometimes also applied to cases where the formation of water or another simple molecule does not occur, as in 'benzoin condensation'".[18] --Itub (talk) 09:10, 23 September 2008 (UTC)

Bless this talk page. The Condensation reaction article includes benzoin condensation as an example. It'd be nice to either exclude it from that list or somehow make a comment to some effect? I'd be bold and all that crap but not if it's going to make work for someone else... Freestyle-69 (talk) 23:37, 24 September 2008 (UTC)

I say be bold. I don't mind either solution (removing it from the list or add a note saying that it is not technically a condensation but it is called that way for historical reasons). --Itub (talk) 11:11, 25 September 2008 (UTC)

Well that one was easy, guess now I've opened my trap I'll have a play with the the benzoin one. Thanks Freestyle-69 (talk) 23:01, 25 September 2008 (UTC)

Polyethyleneterephthalate#Re-crystallization

This section seems dubious to me, though I am no polymer chemist. Anyone care to have a look? Yilloslime (t) 22:34, 23 September 2008 (UTC)

I think that somewhere in those words was some kind of information, but the section is poorly written and seemed to be some sort of instruction or guide to recrystallization from a glassy state. So I deleted the section.--Smokefoot (talk) 23:08, 23 September 2008 (UTC)

Biosynth of oxazoles

Hey guys, I want to replace the image on oxazole with Image:Biosynthesis_of_oxazole.png. I removed all the English text, replacing with numbers so that it can be used on other wikis. What do you think? Too many colors? Or not enough? Or the blue and black colors are jarring? Appreciate comments, so that I can tweak them. Thanks. --Rifleman 82 (talk) 13:47, 25 September 2008 (UTC)

I think it looks good - the colors are not jarring to me. -- Ed (Edgar181) 16:35, 25 September 2008 (UTC)

Approve. I think it is a good example for the use of colour in reaction schemes. Physchim62 (talk) 17:43, 25 September 2008 (UTC)

Thanks for your comments, guys! I've inserted the new image. This topic is not my speciality; if a better caption is possible, do edit it. --Rifleman 82 (talk) 18:04, 25 September 2008 (UTC)

What about "- H₂" (or "+ 1/2 O₂ -H₂O") instead of "[O]"? Cacycle (talk) 02:49, 26 September 2008 (UTC)

My thoughts on the caption. Some may not be familiar with the [O] symbol. Would be nice to have the "(1) Enzymatic cyclization. (2) Elimination. (3) [O] = enzymatic oxidation." on a second line but I don't know how... Freestyle-69 (talk) 04:28, 26 September 2008 (UTC)

Thanks for that. I took up Freestyle's suggestion instead of Cac's because even though it is most logical, it's a bit of extrapolation. --Rifleman 82 (talk) 06:01, 26 September 2008 (UTC)

I inserted a line break as suggested by Freestyle-69. (You just have to insert the HTML code <br/>.) --Itub (talk) 08:37, 26 September 2008 (UTC)

Structure of resiniferatoxin

Hey guys, an IP left a message at commons:Image talk:Resiniferatoxin.svg today regarding the ester side chain on the structure. The current image is correct according to PubChem, KEGG, Sigma-Aldrich, and the Dictionary of Medical Products, but not according to Wender et al—the IP's suggestion matches their article. I'd usually go with the peer-reviewed literature, and, in fact, several articles note that resiniferatoxin has a homovanillyl side chain, but—are all the databases wrong? :) Fvasconcellos (t·c) 17:17, 26 September 2008 (UTC)

Chemical Abstracts has a structure for resiniferatoxin (CAS#57444-62-9) that matches the Wender paper. That structure is found in >402 papers abstracted by CAS. Chemical Abstracts also has the structure that matches the PubChem, etc. structure (CAS#1024342-84-4). There are zero references for that structure. Since only one structure shows up in the primary literature, I would definitely go with that one, despite the inconsistency with multiple public databases. -- Ed (Edgar181) 19:17, 26 September 2008 (UTC)

Thanks, Ed. Uploading the new structure now :) Fvasconcellos (t·c) 19:37, 26 September 2008 (UTC)

TfD nomination of Template:Fchm

Template:Fchm has been nominated for deletion. You are invited to comment on the discussion at the template's entry on the Templates for Deletion page. Thank you.Rifleman 82 (talk) 04:07, 5 October 2008 (UTC)

Monsieur Frémy

I ran into an article that says that KHF₂ is known as "Frémy's salt", but there is another Frémy's salt - a stable radical anion. Apparently, he decomposed KHF₂ to make for the first time HF. Those looking for a project of willing to offer advice:

• We dont yet have an article on KHF₂, which is semi-important industrially. I was thinking of moving bifluoride to KHF₂ - is that a bad idea? Maybe we should have an article on the anion and a separate one on the salt.
• Has anyone heard if there two Frémy's salts?
• Our HF articles - Hydrofluoric acid and Hydrogen fluoride - don't mention its discovery, which seems like an oversight.

--Smokefoot (talk) 18:28, 5 October 2008 (UTC)

I'd never heard of any Frémy's salt until half-an-hour ago! But the one we have an article on is certainly called that. Hydrofluoric acid was being used to etch glass in the 17th century, according to Greenwood and Earnshaw, and was also prepared by Scheele. French Wikipedia credits Frémy with being the first to prepare anhydrous HF, which sounds reasonable–he certainly did work on fluorine chemistry. The bifluoride anion is a nice example of divalent hydrogen, so we might want a seperate article on KHF2. Physchim62 (talk) 20:10, 5 October 2008 (UTC)

I would prefer having a separate article for the anion itself, which can discuss general issues such as bonding and solvation, and specific articles on each notable salt. Note that we already have one on ammonium bifluoride. --Itub (talk) 08:49, 6 October 2008 (UTC)

Articles with no talk pages

Many articles of interest to this wikiproject have no associated talk pages, and as a result are not categorized as "belonging" to the wikiproject. I decided to do an experiment and produced a list of all the articles in Category:Inorganic compounds and all its subcategories, recursively (excluding a few "non-chemical" categories, because otherwise we end up including skiing categories!). There were 1850 articles in the resulting category tree, out of which 248 have no talk page. I listed these 248 missing talk pages at User:Itub/Inorganic compounds without talk pages. These should be useful if anyone wants to look at those articles and rate them or just add the wikiproject template. Of course, there are many false positives, or articles that are better classified under "chemistry" or "minerals" rather than "chemicals". And there are also "false negatives" because there can be articles that do have a talk page but do not have the wikiproject template.

If anyone is interested, I also posted the category tree at User:Itub/Inorganic compound category tree. These lists are semi-automatically generated so I can produce other lists. The problem is that the lists can be unmanageably large unless I add lots of categories to the "blacklist" (for example, the list for organic compounds ends up including tens of thousands of articles on proteins and enzymes!). --Itub (talk) 16:54, 6 October 2008 (UTC)

Thanks, that's very helpful! Walkerma (talk) 01:36, 7 October 2008 (UTC)

A trick to get a good list is to get everything transcluding a {{chembox}} or {{chembox new}}, putting 'Talk:' in front of all of them, and run that list through AWB. If it does not contain a {{Chemicals|parameters}}, add one with empty parameters. Maybe something for chem-awb? --Dirk Beetstra ^{T C} 15:28, 7 October 2008 (UTC)

That is true, but I wanted to try to catch the articles with no chemboxes too (not uncommon for stubs). I wanted something that can also help find WikiProject Chemistry articles, and those don't have infoboxes. --Itub (talk) 15:34, 7 October 2008 (UTC)

Actually, I've done that before, around 27 June. Of course, I'm happy to do it again, but we shouldn't pretend it's perfect, like Itub says. --Rifleman 82 (talk) 17:46, 7 October 2008 (UTC)

Chembox news

Just to let people know that {{chembox}} is now fully equivalent to {{chembox new}}, and so editors can (and should) now tag articles with {{chembox}}. The old chembox is currently at {{chembox old}} (logically!). Starting from today, I (and hopefully a few others [hint]) will be changing the template on existing articles, slowly at first to catch any possible bugs in the interface with CheMoBot, then hopefully finishing with a bot run. Physchim62 (talk) 12:40, 7 October 2008 (UTC)

What would be really great would be if those updates included the curated data from the SDF file (hint!). Thanks a lot for this upgrade, PC. Walkerma (talk) 13:13, 7 October 2008 (UTC)

Chembox property count

See User:Itub/Chembox property count. It is a list of how many chemboxes provide a given property, obtained after parsing 4475 infoboxes, plus a few extra tables. This is helpful for finding certain errors in infoboxes, such as typos in the parameter names, and for things like seeing how many pKa's we have available. I have all the data loaded up into a SQLite database (3 MB), in case anyone is interested. The parsing is not perfect, but appears to be mostly functional. With the database it is easy to produce a table for a given property, such as a table of pKa's. --Itub (talk) 12:34, 8 October 2008 (UTC)

I took a whack at fixing some User:Itub/Chembox property count#Properties used by only one chembox...removed if, added comments for where I got stuck. DMacks (talk) 02:16, 22 October 2008 (UTC)

Best Practices for skeletal images

From Talk:Caffeine#Is the image of the Caffeine Molecule correct? (among other places), lay-readers can understandably get confused by "all the missing atoms" in standard skeletal diagrams. It would be helpful if the image description had a link to skeletal formula so anyone who cared to read about the image could learn what the heck it meant. DMacks (talk) 02:00, 22 October 2008 (UTC)

Personally, I think that we overuse skeletal images - professional chemists are comfortable with them, but a page like acetone is more likely to be read by an undergraduate or A-level student, and some of them will be baffled by the strange lines in the structure page. A link to the skeletal formula article is a good idea with more complex cases, but an unnecessary complication for simple molecules. I think a skeletal formula is fine for drawing oleic acid or bleomycin, but it's inappropriate as the only representation for something very common with only two or three carbons. Walkerma (talk) 15:59, 28 October 2008 (UTC)

Flagging validated/curated data in chemboxes for users

We are currently uploading validated and curated data into chemboxes (see Wikipedia:WikiProject Chemicals/Chembox validation). However, there is no way for a random user to distinguish whether a CAS number was supplied by CAS, or typed in by someone's pet monkey. So we would like to clarify this for users, and we've tested out a parameter that indicates data as validated, and if the entry is edited at all the "validated" flag disappears. You can see an example here, where the CAS# is one supplied by CAS - so in fact we already have a working method that could be implemented. It relies on Beetstra's bot, which defines a particular version from an article history as the source of the validated data.

We were thinking of a color-coded scheme, something along the lines of:

• Green/bold => Validated against a reliable source (i.e., as reliable as it can get)
• Yellow => Checked by a WP:Chem member
• Black => Unchecked
• Red => Recently edited, needs checking

Although a link would be needed to explain what the codes mean, we have to assume that most users wouldn't click on that, and so having something that is intuitive (most people associate green=good, red=bad) would flag it sufficiently even for a user who didn't click for a definition. The exact details could be debated.

I could have posted this at the ChemBox discussion area, but this seems to have broad implications - AFAIK, this could be the first place on Wikipedia where validated content is flagged as such - so I thought we should raise it here, where many more people are likely to see it. So, does anyone have any comments on how best to do this? Cheers, Walkerma (talk) 16:13, 28 October 2008 (UTC)

Just a general comment: In de-WP, we declared it compulsory to use ref tags for all non-trivial parameters in the chemboxes (see e.g. Methan). The CAS number is treated as a trivial parameter that does not need to have a reference, but it can normally be checked in one the references for other properties. What you intend to do here seems to be similar to a certain extent to what is proposed as quality versions. :-) --Leyo 17:50, 28 October 2008 (UTC)

I like Green Bold as shown to indicate the reliable source. Yellow to red etc makes sense to me also. The Black vs red makes less sense. I would leave three levels of red, yellow, green. Red by default should mean unchecked in my view.--68.33.211.217 (talk) 20:12, 29 October 2008 (UTC)

I don't like red for the last stage: it would be confused with redlinks. Let's keep it at a three-level scheme for the time being, if need be we can expand it later. Physchim62 (talk) 21:02, 29 October 2008 (UTC)

OK, let's meet on IRC tomorrow and (hopefully) we can implement this starting tomorrow. We need to start using it as we add validated data in the coming weeks. If you can't make it, please leave any comments here. Walkerma (talk) 02:02, 11 November 2008 (UTC)

Three-level is easy. "If the ref-field matches one of certain known values (CAS for cas#, certain datafile notations for SMILES, etc.) do fmt1, otherwise if it's not blank (i.e., has some unknown value) do fmt2, otherwise (i.e., no ref-field value) do fmt2". Because each field has its own formatting template, each can recognize appropriate "known" refs and include or not an actual footnote or other ref text (to balance clutter vs verifiability and "trivial/obvious", etc. DMacks (talk) 02:10, 11 November 2008 (UTC)

...and now implemented for CAS#s. Consider Boric acid:

• not-quite-reliable source
• authoritative or other known-good source
• unverified

DMacks (talk) 15:39, 11 November 2008 (UTC)

Yellow is pretty much invisible... although that can be a good thing if it's used to flag unreliable data? :) Fvasconcellos (t·c) 16:16, 11 November 2008 (UTC)

Yes, we're discussing it on IRC now. I think dmacks has already changed it - do a refresh! Join us if you can, Walkerma (talk) 16:24, 11 November 2008 (UTC)

The formatting action happens in {{chembox val fmt}} DMacks (talk) 16:54, 11 November 2008 (UTC)

"Join us if you can"

Oops...

The new color looks much better. When (and how) does this start to roll out? I'll start uploading the last set of validated data (401—500) tomorrow, by the way. Fvasconcellos (t·c) 00:42, 12 November 2008 (UTC)

Actually, I see Martin has claimed those entries. Should I work on 100–200 instead? Fvasconcellos (t·c) 00:47, 12 November 2008 (UTC)

The new system is now enabled, so you can start using it straight away! Remember, only use green for the CAS-validated CAS#s for now. Yes, why don't you take 100-200. I will get onto 400+ once the 1.0 work dies down. Our article selection is now complete (an immense task) now I'm on the indexes. Antony should have a new set for us in a fortnight or so. Walkerma (talk) 04:50, 12 November 2008 (UTC)

• Its probably a good thing. I see some good results, e.g., in boric acid. But not being in on the development, can anyone please point out how it works? Wim van Dorst (talk) 21:06, 12 November 2008 (UTC).

Sodium fluoride under attack again

I ask that others help with controlling the antifluoridation enthusiasts on sodium fluoride. This additive elicits intense feelings from some readers. Wikipedia has set up Opposition to water fluoridation, fluoride poisoning, fluorosis, Dental fluorosis, skeletal fluorosis, and probably some others sites to allow the antifluoridation groups to expound their views at some length. So please lend a hand, especially experienced editors.--Smokefoot (talk) 00:37, 1 November 2008 (UTC)

It seems that issue has self-destructed in a big way, thanks to some intervention from others. I've added what is (hopefully) some basic info into the article, not to appease the anti-fluoride-masses but just to bring into line with similar compounds' pages. I know we're trying to steer away from "How-to" etc and towards MSDSs, but is there a standard "Safety" format that we could follow? Freestyle-69 (talk) 02:03, 3 November 2008 (UTC)

That definitely qualifies as a melt-down. We iodize salt, chlorinate water, hydrogenate food, and inject unconscious patients with iron cyanides, but for some reason a segment of society has really latched on to the water fluoridation thing.--Smokefoot (talk) 02:26, 3 November 2008 (UTC)

Benzyl alcohol

It would be greatly appreciated if someone could have a look at the edits here from the last day or so, since its redirection from Phenyl methanol [19]; I initially reverted some unsourced changes, and would like to know what is the proper nomenclature. JNW (talk) 19:08, 1 November 2008 (UTC)

• According to IUPAC rule A-13.1, I'd say it should be called phenylmethanol. Wim van Dorst (talk) 20:47, 1 November 2008 (UTC).

Do you suggest reversing the redirection? If so, I'd prefer that someone with a better understanding of chemistry than I possess do the honors. JNW (talk) 21:06, 1 November 2008 (UTC)

• Let's give it a few days: others can contribute here too. And then the discussion whether the article should be named phenylmethanol which is less used than benzyl alcohol is a different topic. Wim van Dorst (talk) 22:09, 1 November 2008 (UTC).

Great. Thanks. JNW (talk) 22:14, 1 November 2008 (UTC)

Google data for discussion:

• "benzyl alcohol" - 1,490,000 hits

• "phenylmethanol" - 9,330 hits

Ratio "benzyl alcohol" : "phenylmethanol" = 160:1.

Ben (talk) 19:06, 2 November 2008 (UTC)

Thanks, Ben: thought so. That means that the article should be benzyl alcohol, but the IUPAC name in the chembox should be phenylmethanol. Most important for me personally is consistent use of the name throughout the article, though. Wim van Dorst (talk) 22:34, 2 November 2008 (UTC).

sodium silicate (aka sodium metasilicate)

The structure picture in the chembox is incorrect - I have tried to remove it but its still there. I think it needs a fresh pair of eyes! Can someone take a look at this please.--Axiosaurus (talk) 18:23, 2 November 2008 (UTC)

Why don't you upload a new image in place of this one at commons? (I've deleted the local copy, and it no longer displays automagically). Or, describe it to me and I'll do one up? --Rifleman 82 (talk) 02:18, 3 November 2008 (UTC)

Well the one shown is definitely incorrect, but is there one correct image? I guess that there must be materials of the formula Na₄SiO₄ and Na₂SiO₃, but sodium silicate solutions are probably complex mixtures of oligomers, with varying degrees of protonation. My guess is that the ²⁹Si NMR people have the info. I am no expert, but that's my guess.--Smokefoot (talk) 02:39, 3 November 2008 (UTC)

Crystal structure of Na₂SiO₃: W. S. McDonald and D. W. J. Cruickshank, Acta Cryst. (1967). 22, 37-43. I can make a 3D image if appropriate.

Ben (talk) 10:32, 3 November 2008 (UTC)

Hey Ben, just commented to Axio on my talk that you're probably the best guy for the job - you're the expert for crystal structures. Hope you can help! --Rifleman 82 (talk) 17:26, 3 November 2008 (UTC)

The whole "toxic chemical" thing

Partially in reference to the sodium fluoride issue (above), but as a general concern and question:

As most if not all of us know, pretty well anything will kill us if we ingest/inhale/whatever enough of it. We're scientists, or at least educated in this area, so we know that dose X of jiggazantium will cure our somethingitis, but dose X x 100 will give us 3 legs and a bad case of death. But the masses... in general they read the latest news story, or hear something from a friend (both of which we know are great sources...), and start making their own conclusions. Based on the evidence that they have, they make a pretty reasonable decision and decide that since melamine is toxic, we now shouldn't eat off our kitchen benches. I've found that non-scientists are pretty quick to read the first thing and take that as gospel- everyone's too busy to actually find out more for themselves.

I feel that as editors we're tasked with providing a balanced perspective on topics, but when an MSDS for something says it's toxic, we obviously can't say that it's harmless, even if it's therapuetic/beneficial in low doses. The masses won't generally look at an LD₅₀, as they wouldn't be expected to understand that sort of thing. The average Joe wouldn't read an MSDS (or maybe even know what it is), esp if it's only linked from the chembox. But, I get the idea that WP is the first place that people will go to to check these "nasty chemicals" out. Flattering, but onerous.

So, my question is- could there be some standard form of statement/wording that can be included in the "Safety" (or similar) section to "dilute" or further explain the apparent toxicity of so many compounds that people are exposed to? And for that matter, explain that too much of even the good things will do the reverse? Freestyle-69 (talk) 03:02, 3 November 2008 (UTC) Sorry for a potential can of worms

This toxicity issue is indeed one of the hugest cans of worms. My nearly universal recommendation: we refer to the MSDS, which is more authoritative than we can ever hope to be. In doing so, we dissociate Wikipedia from giving advice (Wikipedia:What Wikipedia is not). When the toxicity is notable, we create articles dedicated to the toxicity, such as cyanide poisoning. In some cases, the toxicity is controversial,, and we create water fluoridation controversy. In yet other cases, the toxicity is chemically instructive, phosgene comes to mind, in which case we discuss the mechanism briefly in the safety section. So my vote is to defer to the MSDS and avoid offering more than a few words. And we cannot be too absolutist, of course. I look forward to hearing other's views.--Smokefoot (talk) 03:25, 3 November 2008 (UTC)

The MSDS, if anything, will scare the average non-scientist even more than necessary. MSDS are generally overly paranoid IMHO, maybe because they are usually provided by the manufacturer and the manufacturer doesn't want a lawsuit, but that's just a guess. Just look at an MSDS for sodium chloride (I'm looking at the Sigma-Aldrich MSDS, but I couldn't find a URL to link to). It "may" be harmful in a number of ways, you need glasses and gloves to handle it, should consider a self-contained breathing apparatus in case of fire, and people inhaling it may need artificial respiration. I guess one can never be too careful, but this looks almost like it was taken from http://www.dhmo.org . --Itub (talk) 06:52, 3 November 2008 (UTC)

An MSDS for sodium chloride. I rather liked "Chronic Exposure: No information found." Surely it should say "causes high blood pressure and strokes", or something similar. ;-) Iain99^{Balderdash and piffle} 23:32, 3 November 2008 (UTC)

Now, my suggestion is the following. Although a link to an MSDS can be useful somewhere, it is better to link to something more scientific. Give the LD50, but put it into perspective by comparing it with well-known substances, both "toxic" and "nontoxic". For example, people might be less scared if they knew that the LD50 of melamin is actually higher than that of sodium chloride! And yes, children have died from sodium chloride poisoning too. My guess is that large amounts of melamin probably don't taste as bad as large amounts of NaCl, and that is what can make it more dangerous. --Itub (talk) 06:56, 3 November 2008 (UTC)

Don't forget that more people die from inhalation of water that from inhalation of any other chemical (except possibly dioxygen). Physchim62 (talk) 23:02, 3 November 2008 (UTC)

I agree MSDS's can be inadequate/overdone/silly. For the bigger picture, I wager most people looking up chemicals on WP to get an idea of "toxicicty" are curious about low levels of exposure, like this data: phthalates have been linked to smaller penis size.[20] Different biological effects are thought to occur from different low level chemical exposures. In general, MSDS's are written for use in concentrated form by workers. I think we should accept a perspective of openness towards including data about toxicity, instead of attempting to fight or marginalize that information. The dirty "c" word comes to mind otherwise...censorship. -Shootbamboo (talk) 03:26, 24 December 2008 (UTC)

Fluorenol

Could someone start an article for Fluorenol (hydroxyfluorene)? Perhaps it has another name, in which case a redirect should be created. Fuzzform (talk) 00:11, 5 November 2008 (UTC)

Also, why on earth does it have that name, since it has no fluorine in it? (PubChem 74318) Fuzzform (talk) 00:18, 5 November 2008 (UTC)

See fluorene. --Rifleman 82 (talk) 03:31, 5 November 2008 (UTC)

I started the article as a stub with some basic physical properties, I'll try to add some text to it shortly. -- Ed (Edgar181) 14:17, 5 November 2008 (UTC)

Approved

User:CheMoBot has been approved this morning, and from now on it is saving logs 'below' Wikipedia:WikiProject Chemicals/Log and Wikipedia:WikiProject Chemicals/Log_2 (see Wikipedia:WikiProject Chemicals/Log/2008-11-11). I am a bit tweaking with it now. The logs are a bit long at the moment, but it is easy to hide parts by adapting the Logline template (User:CheMoBot/Logline), I think everything with a 'level' of 0 can be hidden in the logs.

I will be busy tweaking this all in the next days, please let me know if there are things which should be different. @Admin-template-programmers, it would be nice if I could get some help with User:CheMoBot/Logline, fancy that up a bit. --Dirk Beetstra ^{T C} 12:25, 11 November 2008 (UTC)

I have hidden the 'level=0' messages now (which hides some of this morning which actually got a wrong level assigned) through a change in the template. This hides all edits which are not changing values in the box and are not adding an external link (but the data is still there in the edit mode on the page). Please keep an eye on the hidden ones, if there are ones mistakenly hidden that may be due to a mistake in the bot. --Dirk Beetstra ^{T C} 14:57, 11 November 2008 (UTC)

Francium hydroxide

Francium hydroxide was WP:PRODded by someone. 76.66.195.63 (talk) 06:43, 26 November 2008 (UTC)

I prodded it, together with francium fluoride. These are just speculative, unreferenced stubs on nearly unknown compounds. Although there is some published information in Russian journals from the 1960s and 1970s (that I don't have access to), I very much doubt that it will be enough to justify separate articles. If someone can dig up those journals (and can read Russian, presumably), then the information can be added to the francium article. Funny story: when I was searching for these papers I found some patents for inventions that supposedly can use francium fluoride. They said something like: "or any other alkali metal halide, including ... francium fluoride". As you may know, chemical patents are sometimes a bit broad in their claims... --Itub (talk) 06:53, 26 November 2008 (UTC)

I had a look a while back as well, when francium was up for FA, and found even less than Itub. Given the hassle I had finding info for radium chloride, which certainly is a well defied compound, I can't see us having anything to say on francium compounds that can't go in the main article. Physchim62 (talk) 09:01, 26 November 2008 (UTC)

It could just redirect to a Compounds of francium/Francium compounds article. 76.66.195.63 (talk) 12:40, 28 November 2008 (UTC)

Much simpler to make them redirect to Francium, given the sparcity of information. Physchim62 (talk) 13:01, 28 November 2008 (UTC)

Francium fluoride

Francium fluoride was WP:PRODded for deletion. 76.66.195.63 (talk) 12:38, 28 November 2008 (UTC)

Tagging high resolution PNG images with {{Convert to SVG|chemical}} on Commons

Any opinions concerning my suggestion made on Commons:Category talk:Chemical images that should use vector graphics (please discuss there)? --Leyo 19:52, 1 December 2008 (UTC)

BTW: I just noticed that there are also a few hi reg images in the “local” Category:Chemical images that should be in SVG format. It might be best to move them to Commons instead to simply untag them. --Leyo 21:15, 1 December 2008 (UTC)

I just proposed the deletion of that category... Input would be welcome. Cacycle (talk) 23:01, 5 December 2008 (UTC)

I have started to remove high resolution PNG images from the category, but it will take some time until that work will be finished. Help is welcomed. --Leyo 03:48, 20 December 2008 (UTC)

Do we have a guideline as to what is sufficiently high resolution, and what is not? --JaGa^talk 21:33, 20 December 2008 (UTC)

See WP:CSDG#General, but IMHO it's also dependent on the size of a structure. --Leyo 00:32, 21 December 2008 (UTC)

Silver hydroxide

Since this compound is not very stable, and since it exists primarily in an equilibrium with silver oxide, how about a merge there? --Rifleman 82 (talk) 13:21, 2 December 2008 (UTC)

Yes, I think a merge would be a good idea. As I understand it, it's a compound that (I believe) doesn't exist in pure form, and unlike things like calcium bicarbonate it's not highly important, so I don't think warrants having its own separate page. Walkerma (talk) 04:51, 5 December 2008 (UTC)

I agree with the proposed merge. I started this article for reasons that I forget but are not compelling. We have articles on related species that are invoked but are even less "real" - silicic acid and titanic acid, which probably should be incorporated into silica and titanium dioxide.--Smokefoot (talk) 05:00, 5 December 2008 (UTC)

Potassium carbonate

Sanity check for the spacefill model? I'm expecting some sort of crystal lattice comprising K⁺ and CO₃^2-, not an covalent K-O bond. --Rifleman 82 (talk) 16:16, 6 December 2008 (UTC)

Depicting ionic compounds graphically can be a bit tricky. It could be argued that the 2D skeletal structure is deficient because it doesn't convey information about the true solid structure. But at least it conveys important connectivity information. When it comes to a 3D structure, however, I don't think ionic compounds should be depicted like the one currently in potassium carbonate, because a 3D structure should convey more than just connectivity information. An image depicting a crystal lattice would be ideal, but the current image adds no useful information to the article and could certainly be considered inaccurate. I would prefer to see it removed. -- Ed (Edgar181) 20:02, 6 December 2008 (UTC)

I agree that this should not be done this way. However, it would be nice to show the 3-D structures of polyatomic ions, e.g. to illustrate the symmetric trigonal planar structure of the carbonate anion. Cacycle (talk) 00:05, 7 December 2008 (UTC)

I've been working on an image of the crystal structure of K₂CO₃ for Potassium carbonate, should be ready soon. There is a 3D pic of the carbonate ion at Carbonate.

I think 2D structures can be useful for ionic compounds, as seen in Ammonium nitrate and Ammonium carbonate - they take much less time to understand than an image of the crystal lattice and the stoichiometry is often clearer.

Ben (talk) 13:29, 7 December 2008 (UTC)

OK, new image is in place at Potassium carbonate.

Ben (talk) 01:01, 9 December 2008 (UTC)

Very nice! Thank you. -- Ed (Edgar181) 02:09, 9 December 2008 (UTC)

Dioxin

Given the scariness of Irish pigs these days, this may be of interest to anyone that can offer advice or clean up the page a bit. Cheers, Freestyle-69 (talk) 02:54, 9 December 2008 (UTC)

Image:NisinStructure.gif

Someone wrote to OTRS to let us know that this image is incorrect, they said: "This graphic is wrong. Wrong amino acid in N-terminal position.". Can someone take a look at it & fix if necessary? Thanks, --Versageek 05:20, 9 December 2008 (UTC)

There is something wrong: the figure has a valine at that position but the sequence at the bottom says isoleucine. I don't know which is right, and there are other apparent mismatches where the non-standard aminoacids are labeled with standard names. --Itub (talk) 08:14, 9 December 2008 (UTC)

There are a couple of errors in that structure. I created a new image which I believe is correct based on PubChem, Chemical Abstracts, and one of the papers cited in the article. I also added to nisin a Chembox and a 3D image from the German Wikipedia article. -- Ed (Edgar181) 13:12, 9 December 2008 (UTC)

Molybdopterin

Can someone with access to doi:10.1016/S0162-0134(98)10054-5 please check the molybdopterin article? I'm a bit uncomfortable with the current state of the article, and especially with my structures. I am unsure whether molybdopterin is currently used to refer to the molybdenum-bound pyranopterin ring (as my images show) or to the "open" pyranopterin system (as most databases show), with the molybdenum-bound form simply called a molybdenum cofactor.

I had a nice chat with PatríciaR (talk · contribs) about it this September (at Commons, in Portuguese unfortunately) and she noted that a) the nomenclature is still poorly defined and b) current consensus seems to agree with the structures in the article (that is, molybdopterin is acceptable as a name for the molybenum-bound cofactor). If someone could take the time to review the article I linked above and make modifications on our end as necessary, I would really appreciate it; my PC is still acting up, and I haven't even been able to keep up our curation efforts lately. Best, Fvasconcellos (t·c) 15:35, 13 December 2008 (UTC)

My fairly certain understanding is that the cofactor does not contain Mo, so the caption would ideally be revised. Molybdopterins bind tungsten too. I will edit the report later.--Smokefoot (talk) 15:57, 13 December 2008 (UTC)

End of semester projects?: now its Intro to Astrochemistry

Some monster edits at ammonia, formaldehyde, and hydrogen cyanide. Although many of us like this theme, the contributions seem overly specialized - do others agree? I tried contacting two of the students, but they are unresponsive. Suggestions?--Smokefoot (talk) 23:31, 16 December 2008 (UTC)

I only briefly looked at the additions to ammonia, but I agree most, maybe even all of the new info is way too specialized. I think it should be cut out and put into a sub-page called interstellar chemistry of ammonia or something like that. Yilloslime (t) 00:05, 17 December 2008 (UTC)

Agree. I saw the edits to formaldehyde. It was referenced and obviously a whole load of work, but it sorta swamps the main article. Freestyle-69 (talk) 07:41, 18 December 2008 (UTC)

I think it's great that we have someone to add all this information, but I also agree that it would be best to spin it off in WP:Summary style to have a more balanced main article. --Itub (talk) 00:22, 19 December 2008 (UTC)

Molecular formula vs. structural formula

This edit to acetone points out a possible flaw in the new method of representing substances. The method simplifies editing, and auto-calculates MW, but there seems to be no way of still representing the molecule as CH₃COCH₃. The way I see it, a text-type structural formula is more informative than a simple molecular formula. Granted, we do have one or more diagrams at the top of the chembox, so I don't think it's a big deal, but worth raising. Anyone have any thoughts on this? Cheers, Freestyle-69 (talk) 21:48, 21 December 2008 (UTC)

I agree that structural formulae are preferrable. But for the ChemBox we have just used empirical formulae, following the Hill system (C, then H, then alphabetical). In the lead-off paragraph, usually the first sentence, I have been presenting structural formulas, such as (CH₃)₂CO or CH₃C(O)CH₃. In this way, readers see two kinds of formula and can take the one that is most useful for them.--Smokefoot (talk) 23:39, 21 December 2008 (UTC)

Yup, I've seen the strucforms in the leads of some articles, and I like it- I'll make a point to add them if it's relevant. Thanks, Freestyle-69 (talk) 22:25, 23 December 2008 (UTC) And everyone have a safe and happy xmas/festive season/vacation/holiday/other-politically-correct-alternative :)

"Nitrogen tritoxide"

I noticed this on the page listing requested articles. Is there really such a thing? A google search suggests it's a typo of nitrogen tetroxide. --Rifleman 82 (talk) 10:06, 23 December 2008 (UTC)

My guess is that "Nitrogen tritoxide" is a typographical error. I consulted the bible (Holleman and Wiberg) and indeed a substantial body of work appears to exists for nitrogen trioxide, one form of which is the adduct of NO and O2, en route to NO2.--Smokefoot (talk) 18:32, 23 December 2008 (UTC)

The request was for titroxide, not tritoxide, so the title of this section is a second-degree typo. ;-) I think titroxide is most likely a typo for tetroxide, like google suggests. --Itub (talk) 18:41, 23 December 2008 (UTC)

4-Aminopyridine: why change the article name?

I am curious about the justification for retitling 4-aminopyridine to "Fampridine". My intial philosophical concern is that drugs are chemical compounds, but by replacing chemical names with drug names, we are dumbing down the chemistry. People taking these drugs are, to some extent, deluded into thinking that they are not ingesting real chemicals but some sort of candy. In other words, the practice could be seen as anti-scientific. But maybe I am off-base and too cynical. On the other hand, aspirin trumped acetylsalicylic acid (I would recommend that the redirects go from aspirin to acetylsalicylic acid). It seems that we should adopt some policy on this topic. I recently renamed the obsolete drug "Atoxyl" to arsanilic acid.--Smokefoot (talk) 18:32, 23 December 2008 (UTC)

For drugs, we generally use the INN. In most cases I think this is a good idea because the systematic chemical names are usually unwieldy. 4-aminopyridine may be one of the few where the chemical name is relatively easy to remember, spell, and pronounce. In this case the question may be whether this should be treated primarily as a "chemical" or as a "drug", because the different wikiprojects have different naming conventions. --Itub (talk) 18:49, 23 December 2008 (UTC)

This one seems to be the latest spam attack we have had from the drug companies. As the article itself states, 4-aminopyridine is currently in phase III clinical trials: in other words, it is not yet released onto the market and so there is no reason for calling it by a name which only specialists would know (even if the INN is accurate, I didn't even bother to check). Such moves to give such blatant advanced wikipublisity to prospective pharamceuticals should, IMHO, be beaten back by anyone who spots it. Physchim62 (talk) 19:22, 23 December 2008 (UTC)

Relax, the article was renamed by fvasconcellos (talk · contribs), one of the major contributors of the drugs wikiprojects and according to their style guide. I suggest you take your concerns to him instead of constructing conspiracy theories. --Itub (talk) 20:28, 23 December 2008 (UTC)

Please relax. An International Nonproprietary Name is the very opposite of publicity—as the name "nonproprietary" implies. Its purpose is to reduce confusion, and to prevent drugs being referred to solely by their trade names. As for "prospective pharmaceutical", I have learned that 4-AP has long been used in the symptomatic management of multiple sclerosis, and it has had orphan drug status in the U.S. for years (IIRC) for this very indication. (In the EU, it has orphan status for the treatment of Guillain-Barré syndrome.) Just because a drug company is taking an interest and pushing for marketing approval does not mean my edit was an attempt at "wikipublicity" (I'll have to remember that one :)

Smokefoot, we already have policy (rather, guideline) on this topic. Renaming drug articles to their subject's INN is part of the Manual of Style on medicine-related articles, and therefore overrides our convention of naming articles after the most common designation of their subject as per Wikipedia:Naming conventions (common names)#Exceptions. It's a good guideline and a very useful one—surely you wouldn't have paracetamol renamed N-(4-hydroxyphenyl)acetamide! Furthermore, INNs are always unambiguous, as that is that very purpose. Trade names can be ambiguous (not to mention ludicrous at times) and I cannot imagine using them on Wikipedia—now that would be spam. Even in IUPAC names, while unambiguous, provide a certain leeway as they are based on recommendation and not policy; is dapsone 4-[(4-aminobenzene)sulfonyl]aniline or 4,4′-sulfonyldianiline?

In short, this should have been a textbook example of an uncontroversial move—supported (if not mandated) by guideline and regarding a completely uncontroversial article. I apologize if anyone was offended (or driven to philosophical considerations :), but there is absolutely no reason to be. Seriously. Fvasconcellos (t·c) 20:48, 23 December 2008 (UTC)

By the way, my very multi-religious family is about to kindle the lights for Hanukkah, and I am off to join them as I do every year. If anyone would like further clarification, I'll be back later today. Fvasconcellos (t·c) 20:55, 23 December 2008 (UTC)

I'm not creating conspiracy theories: I have seen one multinational pharmaceutical company edit an article (sloppily, from a traceable IP address) then release the drug onto the market the very same week citing the WP article in the press release! It certainly made for an interesting luchtime's editing and emailing.

As for 4-aminopyridine, it is not (yet) a drug: it is in phase III trials. As it has an INN and was granted "orphan" status, it has presumably been used in the past, but for what we don't know. At the moment, we can hardly say that it is primarily a drug; the only evidence we have is that someone thinks it might help patients with Guillain-Barré syndrome. Nothing else in the article allows us to say that it is anything other than a simple organic compound, and so there seems no reason to move the page just because it has an INN. as WP:NCCHEM notes, "no set of guidelines can cover every case". Physchim62 (talk) 22:07, 23 December 2008 (UTC)

WP:NCCHEM also notes "Where a compound has a WHO International Nonproprietary Name (INN), this should be used as the article title." Never mind; I have no personal preference either way. I would request a move, but it appears we already have a rough consensus against it. I have been meaning to move Hydroxyurea to Hydroxycarbamide for quite some time, as it is in de-WP; would you take issue with that? (Seriously, I'd like to know your opinion.) Fvasconcellos (t·c) 13:33, 24 December 2008 (UTC)

• we are supposed to request a move , then discuss a move and then execute a move after a consensus is reached. Too often editors just move regardless V8rik (talk) 22:26, 23 December 2008 (UTC)
  • Actually, that is not necessary; what happened to WP:BOLD? :) Moves need only be discussed when their value is disputable (as it has clearly become in this case). Fvasconcellos (t·c) 13:33, 24 December 2008 (UTC)
    • I checked WP:BOLD and it does not apply to moves. Moves are supposed to work like mergers. Start with placing a relevant tag and open discussion. V8rik (talk) 17:33, 24 December 2008 (UTC)
      • Sorry, V8rik, but that is really the "exception" and not the "rule". From Wikipedia:Requested moves:

If the move you are suggesting is uncontroversial and technically possible, please feel free to move the page yourself. Moves are possible (for registered users with accounts over four days old) when the desired name is a red link, or in cases where the target is a simple redirect—a redirect to the current title, with no prior versions in its edit history. After moving a page, update its text to reflect the new title.

If there has been any past debate about the best title for the page, or if anyone could honestly disagree with the move, then treat it as controversial. [...] If the page has recently been moved without discussion, then you may revert the move and initiate a discussion of the move on the talk page of the article. (See also: Wikipedia:BOLD, revert, discuss cycle.)

(emphasis not mine). Anyway, I felt that a move supported by two guidelines (WP:MEDMOS and WP:NCCHEM) and the style guides of two projects (WP:PHARM and WP:CHEM) could not possibly be controversial, and treated it as such. It was clearly a poor assessment on my part. —Fvasconcellos (t·c) 13:38, 25 December 2008 (UTC)

In cases where a compound is primarily known for its chemical use and under its chemical name it is counterproductive to move the article to its less-notable drug name per Wikipedia:Naming_conventions#General_conventions. We might want to clarify that at Wikipedia:Manual of Style (medicine-related articles). Cacycle (talk) 00:29, 24 December 2008 (UTC)

Well, WP:COMMONNAME only applies "Except where other accepted Wikipedia naming conventions give a different indication". How do you think we could go about determining the primary use of a compound—medical vs. chemical? Fvasconcellos (t·c) 13:33, 24 December 2008 (UTC)