User talk:Smokefoot

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Tantalum(V) chloride

Hi Smokefoot, I see that you marked my edits with hazmat/safety information as spam. I'm looking for official guidance on what can and can not be used in terms of external links. I see multiple pages where other vendors provide links not only to the actual documents of safety data sheets but actually to their product pages and we didn't add any promotional data. For example, https://en.wikipedia.org/wiki/Tantalum(V)_ethoxide has links to commercial sites of three vendors. We only meant to provide meaningful and helfpul information and tried to follow and replicate existing practices (I can bring tens of other pages like that with links to commercial sites). Moreover, the links are created with the nofollow tag automatically so not sure why our posts were marked as spam. Please advise on what the correct approach should be and we'll comply with the guidance. — Preceding unsigned comment added by Rytrom (talk • contribs) 03:59, 6 January 2020 (UTC)

Thank you for your note.

1. Wikipedia does not offer advice to its readers (or should not). I think that the rules are here: WP:NOTADVICE or WP:NOTMANUAL. Safety notes should refrain from telling readers what they should and should not do, wear, etc. Wiki presents facts.
2. See Wikipedia:Manual of Style/Chemistry#Safety. In the Chemistry project, articles usually do not have a Safety section unless the chemical is extraordinary: cyanide, strychnine, nerve gas, etc or the chemical is common/pervasive, e.g. vinyl chloride, hydrazine, household stuff, etc. TaCl5 and Mo(CO)6 are pretty specialized chemicals.
3. I guess one could spoon out some TaCl₅ and rub it into one's eyes or skin, but we cannot protect morons from themselves. We also do not tell readers not to hit themselves with hammers.
4. If it seems that acompany is using Wikipedia as a publicity platform, such behavior is probably inappropriate. If you are keen to help users of chemicals, please consider the comments above. In general, editors are triggered by any editor who repeatedly cites a company/institution/author. That is the reason for my accusation of spamming.

• I have no standing in Wikipedia, aside from being an active editor. You might elevate your question to Wikipedia talk:WikiProject Chemicals. There you would get a more official (consensus-guided) response better grounded on official policy. With best wishes, --Smokefoot (talk) 12:04, 6 January 2020 (UTC)

Smokefoot, thanks for the references. It does help and I agree that TaCl5 is not the most dangerous product. What I'm seeking to hear from you (as one of the most active chemical editors) is an approach that is consistent with the wikipedia approach and doesn't discriminate our company against others. For example, in the tantalum ethoxide link that I mentioned before there is a footnote to the "hazard" group of the parameters to a vendor site. Right under it there is a "External MSDS" link pointing to another vendor site. If it is acceptable and we can add such a link to TaCl5 and other products it will solve our issue. Please advise. — Preceding unsigned comment added by Rytrom (talk • contribs) 17:20, 6 January 2020 (UTC)

Dear Rystrom: I confess that I dont know answers to your question so I am going to reproduce our conversation and maybe get something entered into our manual of style. --Smokefoot (talk) 22:59, 6 January 2020 (UTC)

Your intention is not to improve Wikipedia articles but to spam. --Leyo 23:25, 6 January 2020 (UTC)

Leyo, I see where you're coming from but it is subjective. The reason of my question is that there are many compounds that don't exist today in Wikipedia and we're considering adding them. However, being a commercial company we expect to create some links to our product pages. Trying to find an appropriate and not-discriminating way of doing it (as you can see it is not right now with the page that I brought as an example). — Preceding unsigned comment added by Rytrom (talk • contribs) 00:01, 7 January 2020 (UTC)

[Rh(CO)2Cl]2

What is the problem with the addition the E and C analysis with [Rh(CO)2Cl]2 ? — Preceding unsigned comment added by Golfpro996 (talk • contribs) 14:45, 2 February 2020 (UTC)

@Golfpro996: Wikipedia is not a mechanism for one to cite one's own papers or those of one's friends. That behavior can appear self-absorbed, and it does not further the cause of Wikipedia. And it is against the COI rules. If you want to broadcast your papers and those of your friends, then you might start a blog.

There are 2900 articles on [Rh(CO)2Cl]2. Should we aim to cite most of these? Probably not. Or maybe the 700 papers that have appeared in the previous 10 years? Probably not again. So why should we cite your specialized reports? Because you want to help readers? Or help your legacy and that of your pals? The reports you cite are not even widely cited (not in top 100). The parameterization that you refer to is niche. Please, then, try to keep the citations rather general and just avoid COI. Textbook or reviews are our mainstay. We could really use a skillful chemistry editor, but editors must be able to take a broader perspective.--Smokefoot (talk) 14:59, 2 February 2020 (UTC)

Hello, Smokefoot. You have new messages at Nwbeeson's talk page.
Message added 20:17, 9 February 2020 (UTC). You can remove this notice at any time by removing the {{Talkback}} or {{Tb}} template.

Entertainment

While we're on the topic of entertaining chemistry I was particularly amused by this recent paper doi:10.1021/acs.inorgchem.9b03563. Absolute top marks for the image - the paper has nothing to do with cows or radioactive milk but if you saw it you'd definitely pause to read the abstract. --Project Osprey (talk) 01:18, 20 February 2020 (UTC)

EMACs

I did not understand your message about EMACs. In my changes I preserved the name and the abbreviation. While chemists who work on them may call them just "EMACs" or "extended atom chains", that is not a suitable name for the more general readers, including chemists of other persuasions; adding "cluster" is the least that is needed to make the name suitable for them.
(And the article name must be singular, by general wikipedia tradition. The singular also makes the definition more clear.) --Jorge Stolfi (talk) 00:48, 2 March 2020 (UTC)

Thank you for the message. Now we are talking. The starting point is that Peng and Cotton, call these chains EMACs. They invented the acronym and the name. Probably some sort of ego-thing, but that does not matter. It is the jargon that chemists (about a grand total of 20 in the world, perhaps) call these things. There are other sorts of one-d materials aside from EMACs. A book series by Joel Miller describes them. Linear chain compounds are one example for which Wikipedia has no article. Examples: Krogmann's salt and Magnus's green salt, they might be of interest.--Smokefoot (talk) 01:11, 2 March 2020 (UTC)

We have been through this before. Wikipedia is not meant to be written specialists. An article should not be written and named according to the jargon of the few specialists who work on that topic. At the very least, the contents and name should be appropriate to anyone who has basic knowledge of chemistry, and may run into the name somewhere. "Extended metal atom chain" does not make sense for anyone who does not already know what they are. --Jorge Stolfi (talk) 17:16, 2 March 2020 (UTC)

EMACs is established terminology for a fairly narrow set of compounds. Anyway:

1. what makes you think that you have the insights to rewrite history, create new definitions?
2. who are these readers who want to know about EMACs and coincidentally are unfamiliar with advanced inorganic?

I can see that you are being well-intentioned but the idea or replacing established jargon with your own jargon seems wrong. Should we rename condensation reaction to bond formation with release of water because condensation does not make intuitive sense to the average reader who knows no chemistry? Hard and soft acids and bases to Theory of the influence of atomic polarizabability on bond strength?

We dont want to get into rewriting history because the editor after you might not be so enlightened or so generous in intent. Following your policy that we relabel articles for some semi-arbitrary readability, the next editors might be trolls who want to rewrite history, something that is rampant in the world. We could go on and on about this. So I think what you are proposing is dangerous. Admit it: advanced chemistry is, gulp, difficult material. --Smokefoot (talk) 01:18, 3 March 2020 (UTC)

Well,

1. I must insist: a wikipedia article about a subject should not be written for the few specialists who care about it. It should be written for any reader who has the minimum necessary knowledge to understand what the concept is. Thus, specialized jargon -- in the title or elsewhere -- should be used only when really necessary, with definition or wikilink.
2. As for "condensation reaction" etc: That generic target reader does not have to know the common name of the concept (this information, in fact, is the first goal of the article). However, the title of the article must be the name that a chemist would use when trying to communicate with such a reader -- not necessarily the name he would use when talking to his fellow specialists. Thus, the title may have to include qualifiers that the specialists do not normally use among themselves; like "condensation reaction" instead of just "condensation", or "Grignard reagent" instead of just "Grignard".
3. In particular, the title of an article should never be an acronym, but the phrase that the acronym stands for -- even if the acronym is much more used than the phrase, by those who work in the area. Thus the article about the US is titled United States, not US -- which is just a redirect to it. Even because the acronym may have other meanings in other fields that the reader is familiar with. (EMACS happens to be my preferred text editor, for instance...)
4. As for Peng et al and rewriting history: the authors who first described a concept in print do not have any extra "rights" to choose the name of the Wikipedia article about it, or even its definition. There are uncountably many articles whose topics started with a narrow (or wrong) definition that was broadened (or fixed) over time, and with a name that changed over time. If we were to follow that "paternity right rule", the nitric acid article should be titled "spirit of saltpeter" -- in Arabic.

Anyway, take care, and all the best,--Jorge Stolfi (talk) 21:39, 19 July 2020 (UTC)

Atom cluster

You reverted hours of hard work on atom cluster because you did not like something I did. Please. If I misunderstood something (like what was the topic), it was because the article was a big mess, with many contradictory definitons and examples. Before throwing my hard work again, at least take the time to point out my mistakes -- I would gladly correct them. --Jorge Stolfi (talk) 17:22, 2 March 2020 (UTC)

I am very sorry to have caused trouble. You should have announced some intention to rename though. I also have invested a lot in this article, a topic dear to my heart. Notice that I basically agree with your premise, cluster is a big topic. The ones that I am trying to decribe are the compounds, which are not atomic clusters. I will go back and revise and reinstate your wording. --Smokefoot (talk) 01:22, 3 March 2020 (UTC)

Hi, me again. I didn't understand what exactly is your view on that topic now. Seems that you would like two separate articles, one from "chemistry" view and one from "physics" view? What would be the definitions?
All the best, --Jorge Stolfi (talk) 20:49, 19 July 2020 (UTC)

1,6-hexanediol diacrylate

Hi, and thank you for your contributions to Wikipedia. It appears that you tried to give Draft:1,6-hexanediol diacrylate a different title by copying its content and pasting either the same content, or an edited version of it, into 1,6-Hexanediol diacrylate. This is known as a "cut-and-paste move", and it is undesirable because it splits the page history, which is legally required for attribution. Instead, the software used by Wikipedia has a feature that allows pages to be moved to a new title together with their edit history.

In most cases, once your account is four days old and has ten edits, you should be able to move an article yourself using the "Move" tab at the top of the page (the tab may be hidden in a dropdown menu for you). This both preserves the page history intact and automatically creates a redirect from the old title to the new. If you cannot perform a particular page move yourself this way (e.g. because a page already exists at the target title), please follow the instructions at requested moves to have it moved by someone else. Also, if there are any other pages that you moved by copying and pasting, even if it was a long time ago, please list them at Wikipedia:Requests for history merge. Thank you. Robert McClenon (talk) 01:38, 4 March 2020 (UTC)

Well I really screwed that up. I have made the mistake previously and have been similarly reprimanded. My sincere apologies. --Smokefoot (talk) 01:58, 4 March 2020 (UTC)

Copying within Wikipedia requires attribution

Thank you for your contributions to Wikipedia. It appears that you copied or moved text from Sulfite into Sulfite food and beverage additives. While you are welcome to re-use Wikipedia's content, here or elsewhere, Wikipedia's licensing does require that you provide attribution to the original contributor(s). When copying within Wikipedia, this is supplied at minimum in an edit summary at the page into which you've copied content, disclosing the copying and linking to the copied page, e.g., copied content from [[page name]]; see that page's history for attribution. It is good practice, especially if copying is extensive, to also place a properly formatted {{copied}} template on the talk pages of the source and destination. The attribution has been provided for this situation, but if you have copied material between pages before, even if it was a long time ago, please provide attribution for that duplication. You can read more about the procedure and the reasons at Wikipedia:Copying within Wikipedia. Thank you. If you are the sole author of the prose that was moved, attribution is not required. — Diannaa (talk) 14:24, 16 March 2020 (UTC)

I do a lot of editing, and I leave edit notes, some of which are even useful. I move text and figures from article to article as well, routinely. Probably a few thousand cut and pastes. In any case I will make an effort once again to acknowledge such relocations. Thank you for your diligence and advice. Feel free to offer additional guidance. --Smokefoot (talk) 15:25, 16 March 2020 (UTC)

Tetraethyllead

Hi Smokefoot, I am currently working on the extension of the Tetraethyllead article in the deWP and I am looking for the X-ray structure of this compound. I searched Scholar several times with different key words but w/o success. Maybe you can give me a hint where I can find it. Any help is welcome. Thank you. --Mister Pommeroy (talk) 16:16, 27 March 2020 (UTC)

@Mister Pommeroy: It is a liquid so the structure would need to be low T, but surprise! It looks like someone grew crystals of an inclusion complex doi 10.1002/anie.199615471.--Smokefoot (talk) 18:32, 27 March 2020 (UTC)

Perfect! Thanks a lot for your quick reply, it´s much appreciated! --Mister Pommeroy (talk) 18:45, 27 March 2020 (UTC)

Acid Dye

Hi Smokefoot, I have noticed that you edited the 'Acid Dye' article (Special:Diff/929528696/929535248), and wanted to ask for some clarification as to why. As an example, the carcinogenicity paragraph within the description section was almost completely removed. I am a new wikipedia user, and admittedly very inexperienced, so I understand if my edits weren't up to wikipedia standards. It would be nice if I could hear the reasoning behind your edits, so I'll be able to improve on that next time. Additionally, I really feel like you could be a bit more gentle with your words. 'Awful' and 'poor' are not the words anyone wants to hear when they've spent hours on a project that they sacrificed sleep on (regardless of whether or not the quality reflects this) and whilst I apologise for any wrong edit I made, I would also appreciate an apology on the choice of words. I'm sure you understand why it doesn't feel great when someone else deletes the work you have spent time on and doesn't explain why. I would, however, be open to any constructive criticism and would very much welcome that. --PanisaLuengthada (talk) 09:19, 15 April 2020 (UTC)

Various - fiber rayon etc

You asked about help on certain articles on the talk page of 1,2-diaminocyclohexane. Specifically you asked about dyes, polyester and rayon because I work in Dalton. Delighted to help. Lets take the easy ones first. Dyes- very little experience - my colleague handles that side of the business. Only experienced in pigmenting rayon. I wrote this article Courtaulds Red Scar Works Preston where I worked for 5 years as senior shift chemist. I thus have quite a bit of knowledge about rayon. This site was the largest rayon producer in the UK.

On polyester, my current company takes polyester fiber from recovered carpet and chemically modifies is it to produce a recycled polyol so I can help there. Nylon is already recovered and converted back to caprolactam. I have already written articles on epoxy, polyurethane etc but can also help there. Let me know any specific page that needs work please . GRALISTAIR (talk) 22:25, 15 April 2020 (UTC) @GRALISTAIR: you will notice that caprolactam makes no mention of recycling. Please keep up sharing your knowledge. I volunteer to be your stereochemistry consultant! PS there is some talk about bio-derived 1,3-propanediol - real? --Smokefoot (talk) 22:55, 15 April 2020 (UTC)

Serpentinite

		The Geology Barnstar
		Nice changes. Thanks.Akrasia25 (talk) 23:57, 3 May 2020 (UTC)

Thank you. I very much appreciate the recognition. --Smokefoot (talk) 01:45, 4 May 2020 (UTC)

the S-S bond energy

How do you get the value of S-S bond energy? in this edit you said that the S-S bond energy is 265 kJ/mol. Is there are any reference can be verifiable?-- Nanachi🐰Fruit Tea☕（宇帆·☎️·☘️） 09:58, 9 May 2020 (UTC)

Here are some data from the CRC (Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, Florida: CRC Press. ISBN 0-8493-0487-3. ):

CH3S–SCH3 272.8 ± 3.8 C2H5S–SC2H5 276.6 MeS–SPh 272.0 ± 6.3 C6H5S–SC6H5 214.2 ± 12.6 F5S–SF5 305 ± 21 Hope this helps.--Smokefoot (talk) 15:26, 9 May 2020 (UTC)

• Does the value calculate by (272+272+214+305)/4 ≒ 265 ?-- Nanachi🐰Fruit Tea☕（宇帆·☎️·☘️） 17:24, 9 May 2020 (UTC)

I am unsure of the source of the 265 value, but there is no reason to average the four numbers above. I recommend thta you look around for the BDE for S8. --Smokefoot (talk) 17:54, 9 May 2020 (UTC)

Polymeric structure of PhIO

Hi Smokefoot. It's been a long time! How are things?

I saw you added File:(PhIO)n.png to Iodosobenzene and it reminded me I looked into this structure back in 2016. I looked up your reference, HIJRIC, but saw it has cationic oxygen which will affect the I-O bonding. Carmalt et al., J. Chem. Soc., Chem. Commun. (1994) 20, 2367-2368 (reference #5 in the article) provides some good X-ray powder diffraction evidence that each iodine is coordinated to two oxygens at substantially different distances (unlike HIJRIC). One I-O contact was refined to 2.377(12) Å and the other one was somewhere around 2.04 Å. Hence the dashed bonds in my diagram File:PhIO-polymeric-2D-skeletal.png. Would you consider amending File:(PhIO)n.png to show the asymmetry in I-O bond lengths?

p.s. I did look for secondary sources, but couldn't find anything accessible to me. There are a few textbooks and monographs covering the topic. I found https://books.google.co.uk/books?id=-XkjAQAAQBAJ&lpg=PP6&ots=bw87fZhZ_T&dq=hypervalent%20iodine%20chemistry&lr&pg=PA15#v=onepage&q=hypervalent%20iodine%20chemistry&f=false but the relevant pages (pp. 14-15) are not available in the preview.

Ben (talk) 22:36, 29 June 2020 (UTC)

Hi Ben. Long time, no talk. Nice to hear from you. We did a lot of good work together before your graduate school immersion. I hope that worked out.

Your impact was substantial, dismissing the myths of structural inorganic and PhIO is one that both of us were wondering about, and were both suspicious of the molecular structure for a totally insol material. and you made a nice drawing that should have been put into the chembox vs hidden out of sight.

Yes, you are correct that my image is only an educated guess. But here's my argument. My structure was based on the interior of an oligomer that was capped with a proton or Mg2+ (I forget). A real single crystal result vs powder data, which I assume is superior. The paper (Arnie Rheingold stucture) discussed relevant precedents, one that struck me was PhI=NTs (not in CSD), which has your unsymmetrical structure. I surmized that the asymmetry of PhI=NTs is a consequence of bulk. I could not rationalize why the polymer would undergo such a Peierls distortion unless it is really I=O----I=O (Ph's omitted). One more complication: my feeling/intuition/memory that PhIO is always hydrated, maybe with formula H(PhIO)nOH (where n is large). So the polymeric structure is relevant. --Smokefoot (talk) 01:45, 30 June 2020 (UTC)

I enjoyed those mythbusting days, it was fun working on structural chemistry here with you. I must have decided the PhD needed my attention more than Wikipedia did at the time - probably a good decision as everything turned out well. Glad to be back, now.

I'm not emotionally attached to the PhIO image so I don't mind if it's in the chembox, in the main article or not there at all. The mystery of the structure does intrigue me, though. I get your point about rationalising the available evidence and considering the interior of a polymer makes perfect sense. Ivanov, Popov, Boldyrev and Zhdankin, Angew. Chem. Int. Ed. (2014) 53, 9617-9621 concluded the iodine-oxygen bond in PhIO is an I→O σ dative bond.

To make life simpler for us, it turns out the CSD has an answer on a plate: OYALOR from Wegeberg, Frankær and McKenzie, Dalton Trans. (2016) 45, 17714-17722 is a full structure determination from PXRD of microcrystalline PhIO. It does contain zig-zag I–O···I–O chains with bond-length alternation, but there are also close interchain I···O contacts so you get a corrugated sheet of I and O with phenyl groups above and below. Put another way, I/O layers are separated by back-to-back phenyl layers, much like a lamellar phase. The paper also contains interesting synthetic observations and comparisons with PhIO₂. --Ben (talk) 19:14, 30 June 2020 (UTC)

Okay. Right now I dont have the presence of mind to look into the Dalton Trans and review the artwork. But will be compos mentis in a day or three. Congrats on the PhD. Don't let Wiki-anything interfere with your PhD career. I do worry about Wiki-work being professionally unhelpful, perception-wise. So be careful with this hobby. There is nothing better than real refereed articles. --Smokefoot (talk) 21:19, 30 June 2020 (UTC)

Thank you! Wise words. And no rush on the image - it's just a hobby, after all. --Ben (talk) 08:32, 2 July 2020 (UTC)

p.s. I've uploaded some images of the crystal structure to Commons:Category:Iodosobenzene.

Boranophosphate

Hundreds of papers, you say? Reliable sources discussing this subject in significant detail, as opposed to namedrops? Splendid. All you need to find are two to satisfy the GNG. This time tomorrow, I'll just put in for deletion/merge at AfD, saving their presence, in the article (as opposed to being theoretically out there somewhere). This has gone eleven years without proper sourcing, and it's high bloody time there was some. Ravenswing 13:11, 23 July 2020 (UTC)

Wikipedia has lots of articles that need repair. Some problems have been tagged for decades. Here's the CAS summary "Research Topic "Boranophosphate">references (236)>refine "Book Review" (20)>Nucleoside and Oligonucleoside..." Happy editing. BTW, whats the deal with the threats? --Smokefoot (talk) 13:26, 23 July 2020 (UTC)

Diphenyl ditelluride

Hi Smokefoot,

I came across this reagent recently in lab, and saw our article had its skeletal structure as 90° C–Te–Te angles (File:Ph2Te2.png). Is File:Difenylditelluride.png more realistic? The ball'n'stick and space-filling images are also bent. Do you know if there is any known conformational data (is it really even all-planar)? DMacks (talk) 17:40, 1 August 2020 (UTC)

Let me check. I recall it is a 90° version of H2O2. Ben Mills is back with us, and he probably is quicker on the draw than me. @Benjah-bmm27:.--Smokefoot (talk) 17:44, 1 August 2020 (UTC)

Hi DMacks and Smokefoot, thanks for the ping. I had a look, the angles are roughly 90° (C-Te-Te angles are 97.4° and 100.5°, C-Te-Te-C dihedral angle is 90.8°) and it's chiral which is interesting: Woollins and co, J. Am. Chem. Soc. 2010, 132, 16, 5799–5802. I'll make a new model. --Ben (talk) 17:54, 1 August 2020 (UTC)

Secondary Sources

Hello Smokefoot, you said, that you prefer secondary sources. Do you have some good and recent books for inorganic chemistry/cyanides/isonitrile complexes? Because I look all of my informations up on SciFinder and read journal articles, which shouldn't be the primary source. I would be glad, if you could help me out there. Bosslektorkorrektor (talk) 07:44, 6 August 2020 (UTC)

Indeed Wikipedia prefers secondary sources. Actually the really good sources are WP:TERTIARY = textbooks. Those are the most precious sources.

To find reviews, after the search in SciFinder, filter the hits for "document type" and select for "reviews" and "books". With these, select for those with high citations. Hundreds of reviews exist on MCN.

Many newly published chemists start to edit Wikipedia with the goal of highlighting their contributions. That approach usually leads to frustration because Wikipedia is an encyclopedia (= emphasis on general knowledge). We are not so interested in cutting edge articles. I recommend that editors avoid areas where they publish. Rely on your general knowledge.--Smokefoot (talk) 12:58, 6 August 2020 (UTC)

intro rayon

The article now has two - quite redundant starts for defining rayon (in the topmost, I took the freedom of adding the classification as art silk). This was certainly not intended, or was it? The second one looks like it should start with a definition of viscose, because that's what follows. -- Kku (talk) 09:22, 18 August 2020 (UTC)

Dear Khu: thank you for your help. Feel free to edit widely. Many parallel articles once existed on this theme, and I have been merging and cutting/pasting a lot, so redundancies exist no doubt. --Smokefoot (talk) 12:10, 18 August 2020 (UTC)

Cut shot Aromaticity of porphyrin

Rahulsoman (talk) 18:41, 20 August 2020 (UTC) sir you cut-shot my write up about "porphyrin aromaticity" wrote at Porphyrin Page, please tell me a solid reason. Now I feel the write up is not complete and its not clear to reader. Please see the detailed history bellow. I appreciate you changed the heading into a catchy manner, the rest you damaged the sole of write up.

Porphyrins as Model Systems to Study Aromaticity

In general Porphyrins are macrocyclic molecules that shows aromaticity and follows Hückel's 4n + 2 rule, interestingly upon core modification these porphyrinoid macrocycles can show variable aromaticity.<ref>{{cite journal |last1=Schleyer |first1=Paul v. R. |last2=Wu |first2=Judy I. |last3=Fernández |first3=Israel |title=Description of Aromaticity in Porphyrinoids |journal=J. Am. Chem. Soc. |date=December 3, 2012 |volume=135 |issue=1 |page=315 |doi=10.1021/ja309434t |pmid=23205604 |url=https://pubs.acs.org/doi/10.1021/ja309434t}}</ref> Many scientists got attracted to porphyrinoids because of this variable aromatic behavior, [[Annulene]] chemist Emanuel Vogel synthesised first porphyrin [[isomer]]. This 18pi Hückel aromatic porphyrin isomer is named as porphycene.<ref>{{cite book |last1=Kadish |first1=Karl M. |last2=Smith |first2=Kevin M. |last3=Guilard |first3=Roger |title=The Porphyrin Handbook |publisher=Academic Press |isbn=0123932009}}</ref> Later scientists have synthesized various [[Antiaromaticity|antiaromatic]], [[Möbius aromaticity|Mobious aromatic]] and non aromatic porphyrinoid macrocycles.<ref>{{cite journal |last1=Yoon |first1=Zin Seok |last2=Osuka |first2=Atsuhiro |last3=Kim |first3=Dongho |title=Möbius aromaticity and antiaromaticity in expanded porphyrins |journal=Nature Chemistry |volume=1 |page=113 |doi=10.1038/nchem.172 |pmid=21378823 |url=https://www.nature.com/articles/nchem.172}}</ref>

Smokefoot Changed to

Theoretical interest in aromaticity

Porphyrinoid macrocycles can show variable aromaticity.<ref>{{cite journal |last1=Schleyer |first1=Paul v. R. |last2=Wu |first2=Judy I. |last3=Fernández |first3=Israel |title=Description of Aromaticity in Porphyrinoids |journal=J. Am. Chem. Soc. |date=December 3, 2012 |volume=135 |issue=1 |page=315 |doi=10.1021/ja309434t |pmid=23205604 |url=https://pubs.acs.org/doi/10.1021/ja309434t}}</ref> An Hückel aromatic porphyrin is porphycene.<ref>{{cite book |last1=Kadish |first1=Karl M. |last2=Smith |first2=Kevin M. |last3=Guilard |first3=Roger |title=The Porphyrin Handbook |publisher=Academic Press |isbn=0123932009}}</ref> [[Antiaromaticity|antiaromatic]], [[Möbius aromaticity|Mobious aromatic]], and non aromatic porphyrinoid macrocycles are known.<ref>{{cite journal |last1=Yoon |first1=Zin Seok |last2=Osuka |first2=Atsuhiro |last3=Kim |first3=Dongho |title=Möbius aromaticity and antiaromaticity in expanded porphyrins |journal=Nature Chemistry |volume=1 |page=113 |doi=10.1038/nchem.172 |pmid=21378823 |url=https://www.nature.com/articles/nchem.172}}</ref>

The edit was included under "Potential applications". There is zero application from the aromaticity. See also WP:SECONDARY --Smokefoot (talk) 22:14, 20 August 2020 (UTC)

Are you okey with my chemistry writeups

Dear sir, Its really hard to see that you simply deletes few of my writings. If you notice any problems in my writing. Let me know. Rahulsoman (talk) 08:32, 21 August 2020 (UTC)

information from isomer

Good day Smokefoot, your removal of this information prompts me to think about inclusion of related information. If you were in my boat, would you create a entirely new article, caproleic acid|new article from existing "red" llinks or Decenoic_acid#Free_acids_and_esters|adding the information into a related existing article? -- Ktsquare (talk)

@Ktsquare: Do you understand why I reverted your (clearly well-intentioned) contribution? Your paper makes another decenoic acid, not 2-Decenoic acid. If you think that caproleic acid is notable, then go for it. Its fun to start articles. ChemAbs has about 700 citations to it, which seems to prove notability. Olefin metathesis might be a minor part of the story of this chemical, so keep an open mind. Happy editing.--Smokefoot (talk) 23:21, 2 September 2020 (UTC)

Does this edit count as yours or mine?

Hello Smokefoot, I just added your edit on Redistribution (chemistry) to another article, essentially a copy and paste. I added the source which include your edits according to the page history of the source article, out of courtesy. Wikipedia article history counts the latter edit as mine as my account added the sentences and reference to the latter article. -- Ktsquare (talk) 16:10, 18 October 2020 (UTC)

@Ktsquare: Oh, that kind of accounting is not something that I pay much attention to. I have cut and pasted other's work often, and one or two editors have occassionally reminded me that I should be more careful with attribution. Best wishes, --Smokefoot (talk) 19:53, 18 October 2020 (UTC)

Cresol

Hi Smokefoot - a real blast from the past here. Back in the mists of 2011, you merged some stuff to Cresol from, among other things, 5-methylphenoxy. Specifically, listing Bupranolol and Indo-1 as derivatives of p-cresol. But I just absently noticed that they aren't - as far as I can see those compounds (and indeed anything with 5-methylphenoxy in it) is surely another derivative of m-cresol, not p-cresol, which would be 4-methylphenoxy. I'd have just corrected this, but my days of chemistry structures were quite a while ago and it's been sitting there for nine years, so I thought I'd run it past you and check if you agree it was a mistake! Keep up the good work. ~ mazca ^talk 17:44, 19 October 2020 (UTC)

Oh, thank you for the help. If you see anything else, let me know. Otherwise, I wish you all the best as you recede into the mists again.--Smokefoot (talk) 17:52, 19 October 2020 (UTC)

Polyphenols vs tannins

On my talk page, you said: Hey, I left a small rant on the merge discussion vis a vis polyphenol vs tannin. Be assured that my frustrations are with the topic, not you. I kind of wish that I had more time and more knowledge, but it's a fringe area of chemistry. Articles become v difficult to manage once they take on nutritional or medicinal, esp folksy medicinal/nutritional, aspect. The consequence is that such folk-science topics tend to be as weakly edited as they are heavily consulted by normal people.

There is a lot of misinformation in the public about the health effects of these phytochemicals (blueberries are a 'superfruit' because they contain blue-pigmented anthocyanins; pomegranate juice is an "antioxidant superpower"). Polyphenols are extensively degraded during digestion, and their metabolized subunits are impossible to trace and study in vivo for effects on organs or mechanisms of action. It is a 'fruitless' line of research ;>) because it can never be defined for cause-and-effect. The Oregon State University LPI has a good handle on the overall literature, as their nutritional biochemists have studied polyphenol metabolism and published about it over decades, leading to this conclusion about the weak possible health effects of polyphenols and tannins. For your merger proposal, there isn't much editor interest. You could type notes to individual editors to ask for their opinion on the merge talk page. I think the simplest solution, however, is to close the proposal, not merge, and work together to clarify the articles on tannin and tannic acid. Best to you. Zefr (talk) 16:01, 6 November 2020 (UTC)

terpenes

We're currently cooperating on the terpene article. Ok, enlighten me. Terpenes, being carbon and hydrogen are rather easily defined. Nothing suggests that these can be dissolved in water, and my testy experience suggests that such is a poor procedure. But it depends on who is asking. If a PhD chemist asks, I've seen solubility numbers for water solution, though I can't give you the compound, because I don't remember. A terpene, not terpenoid or terpene alcohol. Are there any? An absolutist statement occurs to me is probably false. What I remember is that a few are very sparingly soluble in water, as in probably if I boil something like cannabis, some stuff will remain dissolved after decanting. Am I stupid? The more complex terpenes will break down under heat and pressure, but go into solution, hmmm... Sbalfour (talk) 01:37, 18 November 2020 (UTC)

When chemists say that something is insoluble, they usually mean very pooly soluble (like 0.1 mg per liter). Tables of solubility data exist, but I dont know of any for terpenes. Now the terpenoids, i.e. terpenes modified by addition of polar groups (OH, C=O, etc), would be incrementally more soluble in water than their terpene counterparts. Typically solubiliy increases at higher temp. And solubility in water inversely scales with mol wt. Diterpenes are less sol than terpenes.

Here is what the "Rubber Bible" Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, Florida: CRC Press. ISBN 0-8493-0487-3. says about the solubility of alpha-pinene "i H₂O; msc EtOH, eth, chl" meaning insol in water (but 0.0000001 g would probably dissolve in a liter) and miscible with those organic solvents. BTW you will encounter disputes about the meaning of miscible (i,e, solubilty of liquids in one another). Organic chemists rarely are interested in quantifying solubility.

I dont know why cannabis would be mentioned on the page of terpene page. I think in the annals of terpenes , cannabis is unimportant because (a) it is terpenoid, (b) it is minor in abundance compared to pinenes and such, (c) it is super complicated structurally, so little pedagical value (IMHO) unless one is deeply into bio-organic chem.

One more comment: solubility is not important aspect of terpenes (or virtually any class of organic compounds). If you look at an organic text, solubility is not a thing. The big topics for any class of compounds are structure and reactions (super rich theme but complicated), apps (few in the case of terpenes), biosynthesis, biological function (probably antifeedants, if any, ).

--Smokefoot (talk) 10:22, 18 November 2020 (UTC)

/* Fuel */ Response: Added sentence with U.S.patent reference about DME use as blendstock in propane autogas to Dimethyl Ether but it was removed.

Dear Smokefoot, I am a new contributor. Yesterday, I made a contribution to the Dimethyl Ether Wikipedia page regarding using DME as a blendstock in propane autogas. I cited US Patent 5,632,786. You removed this contribution on the basis that "patents are unreliable". I appreciate you're being careful. However, this patent is valid based on it being issued by Amoco Corporation; last week I spoke directly with two of the inventors; currently there are on-going efforts by Suburban Propane and Oberon Fuel in southern California to develop this application. Furthermore, this application has been included in a peer-reviewed paper, Literature Cited: Fleisch, T.H., et.al.,"Introduction and advancement of a new clean global fuel: The status of DME development in China and beyond", Elsevier Journal of Natural Gas Science and Engineering, 9, (2012), 94-107. Please either reinstate my contribution with the later journal citation or allow me to do it. Alternatively, please provide guidance as I would like to be a contributor to this Wikipedia subject. Respectfully, XTLExpert001

XTLExpert001 (talk) 13:34, 19 November 2020 (UTC)

Well the main thing is apologies for making your initial editing effort so miserable. II would be glad to help remedy the situation.

People claim all sorts of stuff in patents. Wikipedia is in the business of disseminating general and highly verified knowledge. General knowledge is vetted and vetted. For this reason, Wikipedia relies on reviews and books for big topics like DME. These sources are typically highly vetted. People seeking super specialized info should go to the tech literature.

Then there is the practicalities. About 3 publications (patent, journal article, govt report) appears per day on DME. So Wikipedia should tell readers that this particular patent demands attention? What about the other 10,333 reports that appeared in the preceding decade? Or the 389 other patents issued on DME in 2020?

So your frustration is understandable, but few people realize the scale of the publications out there.

If you are keen to contribute on the topic of DME here are two WP:SECONDARY-quality sources that are highly cited:

doi: 10.1021/acs.chemrev.6b00816

doi: 10.1016/j.cep.2014.06.007

Dear Smokefoot, Thank you for your prompt response. Being patient and persistent and following your guidance, let me cite the Elsevier article, to support my contribution, which was an Invited Review - certainly at least on par with your example 10.1016/J.cep.2014.06.007. The citation directly from ScienceDirect: T.H. Fleisch, A. Basu, R.A. Sills, Introduction and advancement of a new clean global fuel: The status of DME developments in China and beyond, Journal of Natural Gas Science and Engineering, Volume 9, 2012, Pages 94-107, ISSN 1875-5100, https://doi.org/10.1016/j.jngse.2012.05.012. (http://www.sciencedirect.com/science/article/pii/S1875510012000650) Abstract: The last two decades saw the emergence of a new multi-source, multi-market fuel, Dimethyl Ether or DME. Prior to 1990, DME had only found limited commercial use as an aerosol propellant along with propane and butane as a green replacement for the chlorofluoro-hydrocarbons which were outlawed because of their detrimental impact on the ozone layer. DME is an environmentally benign, non-toxic, biodegradable product with physical properties similar to LPG. Global DME annual production capacity is approximately 10 million metric tons and actual market use is reported to be about 3 million metric tons – a remarkable increase from the 200,000 metric tons market demand in the early 2000s. Nearly all of the DME is produced in China from coal-derived methanol via the well known catalytic dehydration process where two molecules of methanol react to form one molecule of DME and one molecule of water. DME is the fastest-growing methanol derivative, yet is still an emerging business with lots of upside opportunities combined with significant challenges. A number of other DME plants are in different stages of development around the world including Egypt, Middle East and Indonesia, all of them natural gas based. Sweden is the leader in the development of bio-DME produced through the gasification and conversion of black liquor, a byproduct in Sweden's paper and pulp industry. Nearly all of today's DME is used as a blend stock for LPG which in turn is primarily used for cooking and heating. At blending levels below 20 vol %, the existing LPG blending facilities, local distribution infrastructure and end-use equipment can be used with minimal (if any) modifications – making for easy marketing. Currently, efforts are underway to commercialize DME as a high-quality diesel alternative. Technical issues such as new fuel injection systems and new fuel additives have been solved and solutions are currently being tested in fleets. This review will describe the history, status and future of DME as a global fuel alternative and how it has and will be changing the global methanol industry.

On page 2 of this peer-review paper are the sentences- "It was shown that blends of up to 20 vol% DME in LPG worked well in standard cooking and heating applications..... Similar blends performed well in automotive applications and were patented by Amoco (US Patent 5,632,786, 1997). Doesn't this secondary source citation support the inclusion of my original sentence "Dimethyl ether can also be used as a blendstock in propane autogas. Note that I would change my original citation to this Elsevier article.

Also, let me add that I am an honorary member of the International DME Association, and an internationally-recognized expert on DME as a fuel. As such, I believe that I am well qualified to contribute what information about DME that are of value to Wikipedia. Currently there are on-going efforts by Suburban Propane and Oberon Fuel in southern California to develop this application using renewable DME. I remain keen to contribute more on developments about DME as a fuel.

I am respectfully requesting that you approve my initial contribution with the above change in the citation. — Preceding unsigned comment added by XTLExpert001 (talk • contribs) 03:20, 20 November 2020 (UTC) --Smokefoot (talk) 16:55, 19 November 2020 (UTC)

What about the other 300+ patents issued on DME in 2020... should we cite them too? Why not? Because you are not friends with those inventors?

• Easy solution: cite the review that cites the (somewhat narrow) patent.
• Your credentials mean nothing here. Nor do mine. We dont work that way here. Its all about sources and objectivity. Difficult to be objective when one is plugging friend's patent.
• Wikipedia is international, so the goings on in s. California or any particular U.S. state is not necessarily significant.
• I am not in charge here. Best wishes, --Smokefoot (talk) 11:45, 20 November 2020 (UTC)

Dear Smokefoot, I am appealing your decision. I have used the Request Dispute Resolution Notice process by using the Template: DRN-notice/doc, which I have edited and published. As I am not familiar with the Wikipedia process, please advise if I have not used the DRN process correctly. I did not see how I could send a DRN other than using the Template. Please correct if appropriate. Thank you. — Preceding unsigned comment added by XTLExpert001 (talk • contribs) 20:08, 20 November 2020 (UTC)

I know about this because I saw the edits at Template:DRN-notice/doc, which is on my watchlist because I'm one of the founders of the Dispute Resolution Noticeboard. I'm hoping to avoid an unnecessary filing there. Are you both willing to accept this edit if it is cited only to the Fleisch, Basu, Sills paper, without any mention of the patent? Regards, TransporterMan (TALK) 21:30, 20 November 2020 (UTC) PS: I saw the DRN filing after posting this, but have removed it because it was manually done, rather than being done through our listing bot. Manual filings break our maintenance bot at DRN and are not allowed. Please consider the question I have asked, above, before relisting at DRN. — TransporterMan (TALK) 21:39, 20 November 2020 (UTC).

Dear Smotefoot. Yes, I am willing to accept posting of my contribution with the reference of the Elsevier paper without any mention of the patent. Regarding the DRN process, I appreciate your correcting my mistakes first filing using the template and then filing manually. I'm still learning. Going forward, I would appreciate your inputs to my future contributions. Regards, XTLExpert001

ArbCom 2020 Elections voter message

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Having an off day?

Hi Smokefoot. I tidied up a couple of oddities you had left in the 1,2,3-Benzothiadiazole article. We all have off days! Mike Turnbull (talk) 16:53, 26 November 2020 (UTC)

Possible copyright issue with an Elsevier book

Hi, you as a chemist might be able to help me with this. I was reading Wiki articles about the chlorides of molybdenum and the came across this book. When I read what it had to say about this topic, the text seemed to be oddly familiar. And it so happens that at least stuff about molybdenum(II) chloride, and molybdenum(III) chloride in the book is either direct copy from Wikipedia word to word or with slight tweaks. The copied version are this and this and the offending pages of the book is 530 (Google Books link). There might be even more directly copied things in this book, I haven't checked. Should the pubisher be contacted? --Nitraus (talk) 13:52, 26 December 2020 (UTC)

Thank you for the note. You are correct, the MoCl2 section is pretty serious plagiarism. Also parts of Nb chemistry are also copied. I emailed the lead author and to Elsevier. My guess is that nothing will come of this incident, i.e. Elsevier will ignore me. The good news is that Wikipedia is so reliable that these three supposedly distinguished scholars decided to copy us!--Smokefoot (talk) 16:15, 26 December 2020 (UTC)

Wikipedia is free to use for any purpose, even commercial, with attribution. Hope a lot of students read the attribution and laugh. How embarrassing for those academics. In fact, Elsevier will blush when they find out (hope they gave attribution). Imagine having to recall hundreds of books. (Which, 2021 being in the future, have not yet been sold.)--Quisqualis (talk) 05:04, 29 December 2020 (UTC)

Pages 536–537 about Ru halides (Google books p. 536, p. 537) contain text copied from ruthenium pentafluoride, ruthenium hexafluoride and ruthenium(III) chloride, with minor alterations. Section about uses of Pd in jewelry (p. 550) is taken almost directly from our palladium#Jewelry, our "citation needed" tags have just been deleted. It is easy to find more examples, most of the book has perhaps been plagiarized from Wikipedia? jni^{(talk)(delete)} 15:13, 2 January 2021 (UTC)

Thank you. The extent of the plagiarism is shocking. When I wrote to the lead author with excerpts from the book highlighting plagiarism, he responded "We have used many different resources to write our book including the chemistry as reflected in the extensive References and Futher reading lists at the end of the chapter. Adj. Prof. Theo Kloprogge" The references do not mention Wikipedia. You are encouraged to contact Elsevier. https://service.elsevier.com/app/contact/supporthub/elsevier/. I would be curious if you can get any comment from the authors. The plagiarism has the potential to be a landmark case.--Smokefoot (talk) 15:35, 2 January 2021 (UTC)

An important part of the process is to find the WP editors who wrote the text on-wiki. They are the ones who have standing to file an actual copyright complaint. DMacks (talk) 18:43, 2 January 2021 (UTC)

Yes good point: individual editors would need to be identified and express ownership... if we get that far. This episode seems relevant. Maybe Elsevier will just stop selling the book, which is my preference. The predicament seems like something that a newspaper would find interesting - big shot scholars with major publisher produce a glossy tome, which turns out to be ... . Also the book is entitled "first edition". The second edition will require Wikipedia to up our game.--Smokefoot (talk) 19:39, 2 January 2021 (UTC)

From The Signpost - if you want to write an article for The Signpost please go ahead. This type of thing has been done before, see e.g. Doc James article at Wikipedia:Wikipedia Signpost/2015-02-25/Op-ed about Oxford Univeresity Press. The comments are also informative. You'll find that it is almost impossible to get the licensed enforced, but if you document the plagiarism thoroughly, and eliminate things like - both Wikipedia and Elsevier paraphrased from the same source, then you can certainly make a ruckus. For example - and this may be overkill -you could report the case to the author's university research ethics committee *and* the student newspaper if the university has one. Let me know if you want to pursue this. email is best. Smallbones_(smalltalk) 00:04, 4 January 2021 (UTC)

Rhenium(VII) oxide geometry

Hi Smokefoot,

Continuing regarding one of our problematic editors, does monomeric Re₂O₇ have linear Re–O–Re geometry? The article says it "closely resembles manganese heptoxide", and manganese heptoxide is citedly bent. But the Mn article says the Tc analog is linear and that the Mn analog resembles Tc. I don't have access to the Wells Structural Inorganic Chemistry ref. Clearly File:Rhenium(VII)-oxide-from-xtal-3D-SF.png is falsely named, since the crystal state is polymeric, with bent M–O–M (doi:10.1021/ic50073a006). I'm trying to decide if that image should be renamed ("gas-phase monomer"?) vs deleted outright ("chemical nonsense"). DMacks (talk) 13:31, 16 January 2021 (UTC)

@DMacks: I dont have Wells with me ,but these molecular oxides appear to have received a lot of attention in recent years, so that book is not so relevant.

• Tc2O7 has a linear M-O-M, centrosymmetric as a solid. doi 10.1021/acs.inorgchem.6b01683. These authors say that it is known to bee bent in gas phase
• Mn2O7 has Mn-O-Mn of 120.7 in solid state (Krebs et al.)
• Re2O7 is bent in gas phase according to IR. According to doi 10.1021/ic950675g, "The Raman and infrared spectra of gas phase Re2O7 are reported. The experimental vibrational spectra of molecular Tc2O7 and Re2O7 are compared with calculated spectra. The results of these studies agree with a nonlinear M−O−M bridge for Tc2O7 and Re2O7". But they dont give a bend angle. I hope this info helps.--Smokefoot (talk) 15:52, 16 January 2021 (UTC)

That's a big help. Thanks! DMacks (talk) 16:35, 16 January 2021 (UTC)

Mix-up at AIV

Hi. Could you take a look at this diff from WP:AIV between an edit in which Horse Eye's Back added a comment and an edit in which you responded? These edits were made 15 hours apart, which means you added your response to a version of the page that was 15 hours old, obliterating all the outstanding reports that were on the page immediately before your edit (one of which was mine), and restoring all the reports that had been there at the time of HEB's comment and had since then been processed and removed. Largoplazo (talk) 17:48, 11 February 2021 (UTC)

I apologize for obliterating. Apparently my addition, well intentioned as it was, was inept and caused extra work for you. --Smokefoot (talk) 17:54, 11 February 2021 (UTC)

Hello

Hi! I reported an IP User. You deleted my report and I don't really understand why. You only wrote "wasted effort". Whad do you mean by this? The user I reported has vandalised the article again. Dante4786 (talk) 18:45, 11 February 2021 (UTC)

Sulfur trioxide

I see you're doing some improvements at Sulfur trioxide. I've never worked with the stuff personally but I've know people who have and I dimly remember them having some mad stories about it. The melting point of the polymeric alpha form is higher than the boiling point of the molten monomer - so heating results in something like explosive sublimation. I seem to recall that the are significant enthalpy changes between the various polymorphs, which makes this extra exciting. You can't buy it from Sigma or any other reputable supplier, probably for these reasons. --Project Osprey (talk) 20:23, 20 February 2021 (UTC)

@Project Osprey:. Although a sulfur guy, I have never worked with SO3. I have a sample of the py adduct, which seems fairly benign. Your comments about hazards of handling the compound align with my expectations - it is nasty stuff that industrial labs are suited to handle vs the cowboy approach employed in academia. The properties of its various forms merit description. Any further guidance you might have would be most welcome.--Smokefoot (talk) 22:11, 20 February 2021 (UTC)

It will have to wait till the working week but I'd have a look. Many chemists enjoy swapping stories of ferocious materials, so I expect there'll be a good summery somewhere.--Project Osprey (talk) 23:30, 20 February 2021 (UTC)

It's actually proving hard to find good references, possibly because academic labs can't buy it very easily. I don't have access to this review but I think it might hold some answers doi:10.1021/cr60220a003. I've found mention of liquid γ-SO₃ being stabilised by trace levels of boron trioxide which prevent it from polymerising - it was at one point marketed under the trade-name of Sulfan but it doesn't seem to be available any more.doi:10.1021/ie50579a019 --Project Osprey (talk) 23:56, 22 February 2021 (UTC)

Copying within Wikipedia requires attribution (2nd request)

Thank you for your contributions to Wikipedia. It appears that you copied or moved text from Hydrocyanation of unsaturated carbonyl compounds into Hydrocyanation. While you are welcome to re-use Wikipedia's content, here or elsewhere, Wikipedia's licensing does require that you provide attribution to the original contributor(s). When copying within Wikipedia, this is supplied at minimum in an edit summary at the page into which you've copied content, disclosing the copying and linking to the copied page, e.g., copied content from [[page name]]; see that page's history for attribution. It is good practice, especially if copying is extensive, to also place a properly formatted {{copied}} template on the talk pages of the source and destination. Please provide attribution for this duplication if it has not already been supplied by another editor, and if you have copied material between pages before, even if it was a long time ago, you should provide attribution for that also. You can read more about the procedure and the reasons at Wikipedia:Copying within Wikipedia. Thank you. If you are the sole author of the prose that was copied, attribution is not required. — Diannaa (talk) 23:38, 22 February 2021 (UTC)

Check it out: I move a lot of content. A lot. And in so doing, I edit the content either as part of the moving/pasting or subsequently. I typically note the source page. Here are two relevant notes from the hydrocyanation reshuffle:

• "Merge proposal[edit source]

Support the 2020 merge proposal to merge Hydrocyanation of unsaturated carbonyl compounds here; best discussed in the context of the broader topic, and will significantly improve this page. Klbrain (talk) 22:50, 20 February 2021 (UTC) I moved it, but tossed a lot of super specialized or inappropriate (procedures and advice) content. It was written by an eager grad student who tended to be repetitive.--Smokefoot (talk) 23:08, 21 February 2021 (UTC)"

• "16:46, 21 February 2021 diff hist +7,019‎ Hydrocyanation ‎ →‎History: start transferring content"

But I will re-read your recommendations and strive to adhere to those guidelines.--Smokefoot (talk) 00:29, 23 February 2021 (UTC)

2-Fluoroethanol

Your recent editing history shows that you are currently engaged in an edit war; that means that you are repeatedly changing content back to how you think it should be, when you have seen that other editors disagree. To resolve the content dispute, please do not revert or change the edits of others when you are reverted. Instead of reverting, please use the talk page to work toward making a version that represents consensus among editors. The best practice at this stage is to discuss, not edit-war. See the bold, revert, discuss cycle for how this is done. If discussions reach an impasse, you can then post a request for help at a relevant noticeboard or seek dispute resolution. In some cases, you may wish to request temporary page protection.

Being involved in an edit war can result in you being blocked from editing—especially if you violate the three-revert rule, which states that an editor must not perform more than three reverts on a single page within a 24-hour period. Undoing another editor's work—whether in whole or in part, whether involving the same or different material each time—counts as a revert. Also keep in mind that while violating the three-revert rule often leads to a block, you can still be blocked for edit warring—even if you do not violate the three-revert rule—should your behavior indicate that you intend to continue reverting repeatedly.

You are violating the three-revert rule!!! Please stop. — Preceding unsigned comment added by Nschndr (talk • contribs) 13:20, 11 March 2021 (UTC)

It appearsss that you are doing a homework assignment without any guidance. Its not your fault, but your teacher's. The article will be rewritten in concise format sooner or later. Tell your teacher or your parents to step in if you feel that you are being mistreated. --Smokefoot (talk) 18:33, 11 March 2021 (UTC).

I am as much entitled as you to write a Wikipedia page, just because you have more experience, does not mean that you are better than I am. If you have any problems with my writing style, all you need to do is comment on them. Instead, you just deleted large parts of my page. I spend hours on making the page and you just deleted it, because? It is not according to your writing style? Talk to me, comment on specific details, but do not just remove thousands of words. Not only is it arrogant to think that your preferences are the only way to write a Wikipedia page, you did not even give me the chance to improve it myself so I could learn from your writing experience. And most important of all, you violated the three-revert rule several times. You are not allowed to delete more than three parts of a page!!! I could file a report and get you blocked from Wikipedia. — Preceding unsigned comment added by Nschndr (talk • contribs) 19:22, 11 March 2021 (UTC)

"Potassium arsenate" listed at Redirects for discussion

A discussion is taking place to address the redirect Potassium arsenate. The discussion will occur at Wikipedia:Redirects for discussion/Log/2021 March 24#Potassium arsenate until a consensus is reached, and anyone, including you, is welcome to contribute to the discussion. Beland (talk) 01:19, 24 March 2021 (UTC)

Vit B5

What did you not like about the sentence "The vitamin circulates in plasma as such; the conversion to CoA takes place after it is taken up by cells."? David notMD (talk) 18:50, 6 April 2021 (UTC)

Re: "The vitamin circulates in plasma as such"

Response: That's what vitamins do.

"The conversion to CoA takes place after it is taken up by cells"

Response: What alternative is there for the prosthetic group to be attached to the cofactor?

Thanks for checking. It is gratifying that someone notices and reassuring that others are monitoring. cheers, --Smokefoot (talk) 22:58, 6 April 2021 (UTC)

It's one of the seven vitamin articles I have raised to GA. Trying hard not to act as if I 'own' them. David notMD (talk) 14:15, 7 April 2021 (UTC)

@David notMD: David, I can be hyperactive, very imperfect editor, so you are welcome to revert or modify my edits. I will not be offended (not that it matters). Although Wiki expects AGF, I rely on AGIBEF (assume good intentions but expect flaws). --Smokefoot (talk) 14:26, 7 April 2021 (UTC)

Adding page number

Hello . Please consider adding page numbers when using {{Greenwood&Earnshaw2nd}}, {{March6th}} and other citation templates - just add page= or pages=. Its so difficult to find the numbers later. Christian75 (talk) 12:03, 16 April 2021 (UTC)

Will do, thank you for the advice. --Smokefoot (talk) 12:52, 16 April 2021 (UTC)

Phosphorus-31 nuclear magnetic resonance

I reverted your contribs because of section contents (previous is more about how it works and following one about chemistry or like). I put image at the beginning of the article because it is the only image in the article and we don't know where it belongs. --5.43.73.49 (talk) 10:04, 11 May 2021 (UTC)

Thanks for the note. Its a spectrum submitted by me, BTW. --Smokefoot (talk) 13:54, 11 May 2021 (UTC)

Gallium(III) sulfate

I have a question why you said there was no evidence. There was plenty of references and there were chemical companies offering it. Isn't this evidence. There is even a document from the University of Michigan. Thank you. Keresluna (talk) 19:43, 11 May 2021 (UTC)

I even found an article describing a successful preparation of Gallium(III) sulfate. Hoping to hear back. Keresluna (talk) 19:55, 11 May 2021 (UTC)

@Keresluna: If you want a good source on inorganic compounds, look for a published crystal structure. If you cannot find a crystal structure, then stay away from a compound because you might not have enough experience to know what is real and what is not real. Companies will say many things, but their websites are not reliable sources. Patents also can be very unreliable. So be careful and skeptical. Titanium(IV) acetate sounds good, but no one has ever made it. Ditto for gallium sulfate as far as I can see.

You seeem to be looking for compounds that have not been described in Wikipedia, but doing that takes serious experience.

If you have some questions, feel free to ask me or other regular editors in Chemistry-Wiki for help. --Smokefoot (talk) 20:29, 11 May 2021 (UTC)

Thanks, though this compound looks good for my experience. Another question: if a source shows a X-ray diffraction pattern is it reliable? Keresluna (talk) 20:52, 11 May 2021 (UTC)

X-ray crystal structure. Most things, pure, mixtures, garbage, etc - give a pattern, but it is the single crystal X-ray crystallography analysis that leads to a 3-dimensional structure.

I searched Chem Abstracts for Ga2(SO4)3: almost nothing. At that stage I realized that you are guessing compounds that should exist based on oxidation states. That approach is admirable and leads to useful thinking, but that approach is also tricky. --Smokefoot (talk) 21:03, 11 May 2021 (UTC)

Another red flag: just Google "gallium sulfate". What do you see? Journal articles? No. Textbook sections? No. Companies trying to sell you stuff? Yes. --Smokefoot (talk) 21:11, 11 May 2021 (UTC)

Thanks for the support. I really appreciate it. I am very sorry if I am just making a mess. Thank you again! Keresluna (talk) 21:13, 11 May 2021 (UTC)

Well maybe you can learn something. For example titanium tetraacetate is likely to eliminate acetic anhydride and various Ti oxo acetate clusters.

My advice - get a great textbook, and use that as a tool to contribute to Wiki-Chem. My favorite is "Chemistry of the Elements" by Greenwood and Earnshaw. Its about 25 years old, but still very useful. The advantage of using a big, famous textbook is that your contributions are more likely to be notable. Notability is a big, big problem for new editors. Not only is gallium sulfate not real, it is not really notable.--Smokefoot (talk) 21:42, 11 May 2021 (UTC)

Moving Compounds of aluminium to Aluminum compounds help

I am trying to move the page Compounds of aluminium to Aluminum compounds because the result of Requested move 5 May 2021 was move. All of the other links are solved but I need help on the aluminum one. Thank you. Keresluna (talk) 18:50, 12 May 2021 (UTC)

Fluorine cycle

This page is fairly new page and I thought it might interest you, as you've had a few battles over fluoride pages in the past. --Project Osprey (talk) 14:43, 10 August 2021 (UTC)

Thank you very much. I missed it. I am semi-vigilant about some forms of antifluoridation, but this article seems sane. There are some folk that associate fluoridation with Nazis, mind control, and all sorts of nutty ideas or innuendos. BTW, a belated thank you for revising polyurethane. Cheers, --Smokefoot (talk) 23:13, 10 August 2021 (UTC)

Limiting things like that to mere facts can be difficult. Polyurethane is still far from resolved, but some sections are a real undertaking and its rare that I have a free day to dedicate to them. Hopefully I'll get there eventually. --Project Osprey (talk) 00:04, 11 August 2021 (UTC)

2-Ethylhexanoic acid

I wanted to know, if possible, in detail, why the method of obtaining the acid was considered wrong, saying that butyraldehyde is used, being the butyraldehyde is the first product of the aldol condensation of ethanol, subsequent hydrogenation. Basquyati (talk) 22:15, 7 September 2021 (UTC)

Thank you very much for taking the time to check. The edits can seem brutal or dismissive because some editors like me are covering a lot of articles and we dont explain things well. Butyraldehyde is produced by hydroformylation on scale. It is not made from acetaldehyde. That reaction is reasonable, but it is "insignificant" in a commercial sense. I dont know why that is the case. Hydroformylation is highly efficient is presumably part of the reason. My general feeling is that (see [[Guerbet reaction| (see Guerbet chem looks good on paper but is messy. A very good review is doi=10.1002/14356007.a10_137. Feel free to ask further. Another issue with your edit, as I recall, was that it is not backed by refs. With best wishes, --Smokefoot (talk) 02:40, 8 September 2021 (UTC)--Smokefoot (talk) 02:40, 8 September 2021 (UTC)

Hydroquinone and your revert.

Hi,

Please join the discussion I started.

PS. According to this source the "come off it" is an informal phrasal verb, "used to disagree with somebody rudely". Was it your intention? 85.193.252.19 (talk) 21:50, 7 October 2021 (UTC)

Your only argument was "come off it", and you ignored my invitation to join the discussion, so I restored my version. 85.193.252.19 (talk) 15:29, 11 October 2021 (UTC)

Featured article review for Shoe polish

I have nominated Shoe polish for a featured article review here. Please join the discussion on whether this article meets featured article criteria. Articles are typically reviewed for two weeks. If substantial concerns are not addressed during the review period, the article will be moved to the Featured Article Removal Candidates list for a further period, where editors may declare "Keep" or "Delist" the article's featured status. The instructions for the review process are here. Hog Farm _Talk 18:52, 16 October 2021 (UTC)

A spooky barnstar for you!

		The Surreal Barnstar
		I don't know what sixth sense or magical energy you were tapping into, but out of everyone here you're the only one able to state truthfully that you opposed the administratorship of an Icewhiz sock. Surreal hardly contains it. Sending love, fellow human. Folly Mox (talk) 02:19, 20 October 2021 (UTC)

thank you for the star. It's a little spooky. Actually, I didnt know that the editor in question was a sockpuppet, but I did catch some flak for commenting that the candidate was not a very assiduous content creator. Best wishes, --Smokefoot (talk) 01:50, 21 October 2021 (UTC)

The Barnstar of Diligence

		The Barnstar of Diligence
		"In recognition of a combination of extraordinary scrutiny, precision and community service." ☆ Bri (talk) 22:43, 20 October 2021 (UTC)

Sometimes it's good to be alone and unafraid. ☆ Bri (talk) 22:44, 20 October 2021 (UTC)

Thank you very much for the recognition and for taking time to contact me.--Smokefoot (talk) 01:47, 21 October 2021 (UTC)

"BaMnO3" listed at Redirects for discussion

A discussion is taking place to address the redirect BaMnO3. The discussion will occur at Wikipedia:Redirects for discussion/Log/2021 November 4#BaMnO3 until a consensus is reached, and anyone, including you, is welcome to contribute to the discussion. ~~~~
User:1234qwer1234qwer4 (talk) 15:53, 4 November 2021 (UTC)

Confusion about TACH ligand

Hi Smokefoot,

While looking at hexahydro-1,3,5-triazine, which is target of the TACH redirect, I see TACH defined as a triazacyclohexane structure (nitrogen instead of carbon as part of the ring). But that article links to cis,cis-1,3,5-triaminocyclohexane, which identifies itself as TACH. In that case, it's triaminocyclohexane structure (nitrogen substituents attached to the ring). I don't know either of these ligands myself. Is there really a widespread ambiguous usage in the literature? If so, we should try to note in those two articles whatever the situation is, and adjust the redirect to point to a disambiguation page if necessary. DMacks (talk) 13:53, 5 November 2021 (UTC)

@DMacks: Good eye. Probably like you, by Googling, I found the acronym applied to both the trazacyclohexane:

• Inorg Chem. 2010 Feb 15;49(4):1283-5. doi: 10.1021/ic902114p. "Triazacyclohexane (tach) complexes of high-valent rhenium: syntheses of [(R(3)tach)ReO(3)](+) (R = -CH(3), -CH(2)C(6)H(5)) and its substitution reactions")

and the cis,cis-1,3,5-triaminocyclohexane:

• Inorg Chem. 2013 Apr 15;52(8):4517-27. doi: 10.1021/ic302819j. "cis-1,3,5-Triaminocyclohexane as a facially capping ligand for ruthenium(II)" PMID: 23517123 DOI: 10.1021/ic302819j.

So you're right and I guess we modify the tach to be a mini disambiguation page. We have a slightly related issue with triphos, which should probably be split and handled similarly.--Smokefoot (talk) 14:28, 5 November 2021 (UTC)

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Carbonyl C-O distance

Hi Smokefoot,

Hope you're well!

I saw this edit you made to Carbonyl_group#Structure, saying the C=O distance in COCl₂ is 1.66 Å. Are you sure that's right? Phosgene#Structure_and_basic_properties says 1.18 Å, while Greenwood & Earnshaw give it as 1.166 Å, i.e. 1.17 Å. They also provide a comparison with carbonyl fluoride (1.174 Å) and carbonyl bromide (1.13 Å).

Ben (talk) 09:47, 14 December 2021 (UTC)

"MoS4" listed at Redirects for discussion

An editor has identified a potential problem with the redirect MoS4 and has thus listed it for discussion. This discussion will occur at Wikipedia:Redirects for discussion/Log/2021 December 27#MoS4 until a consensus is reached, and anyone, including you, is welcome to contribute to the discussion. ~~~~
User:1234qwer1234qwer4 (talk) 20:42, 27 December 2021 (UTC)

COI in edits about bioenergetics

I want to ask your advice about a recent edit by Klaus Schmidt-Rohr here on Fatty acid, and multiple edits by the same person on related pages such as Fatty acid metabolism, Mitochondrion and Cellular respiration that refer many times to the same self-citation. They seem to be clear cases of WP:SELFWP:SELFCITE and reliance on primary research, and I could be bold and simply revert on that basis, warn the editor as you have done previously on their talk page, and invite discussion on the Fatty acid talk page. To make things more complicated, these edits also appear dubious to me, or at least they provide a boldly non-mainstream description of bioenergetics, as they claim "Fundamental Corrections" to long-held understanding. This "correction" appears oversimplified: it seems to ignore the high H content in alkane chains of fatty acids as being important to the high energy/mass ratio they provide through oxidation. But I feel that I'm too much of a non-chemist and WP newbie to be so bold as to revert and discuss the technical and editorial aspects in detail. I'd be glad of you or DMacks or other experienced editors would evaluate and address these edits as you think appropriate, or offer your advice on how to proceed. –MadeOfAtoms (talk) 21:50, 27 December 2021 (UTC)

References

Titanium Featured article review

I have nominated Titanium for a featured article review here. Please join the discussion on whether this article meets featured article criteria. Articles are typically reviewed for two weeks. If substantial concerns are not addressed during the review period, the article will be moved to the Featured Article Removal Candidates list for a further period, where editors may declare "Keep" or "Delist" the article's featured status. The instructions for the review process are here. SandyGeorgia (Talk) 20:49, 11 January 2022 (UTC)

Merger of Alkane stereochemistry into Conformational isomerism

Hi, there has been a recent objection to the merger of Alkane stereochemistry into Conformational isomerism so I was wondering if you would be willing to rejoin the discussion again since the consensus was made a year ago but I want to ensure that this current objection is heard by the original participants of the discussion before I merge and remove this from the backlog. Thanks! -Karthanitesh (talk) 00:59, 19 January 2022 (UTC)

New message from GreaterPonce665

 You are invited to join the discussion at Talk:4-Nitroaniline. GreaterPonce665 ^(TALK) 20:06, 31 January 2022 (UTC)

"Conjugation (biochemistry)" listed at Redirects for discussion

An editor has identified a potential problem with the redirect Conjugation (biochemistry) and has thus listed it for discussion. This discussion will occur at Wikipedia:Redirects for discussion/Log/2022 March 3#Conjugation (biochemistry) until a consensus is reached, and anyone, including you, is welcome to contribute to the discussion. Happy Editing--IAmChaos 01:08, 3 March 2022 (UTC)

List of colleges and universities in the United States by endowment

Please cease arbitrarily (and seemingly randomly) reordering the table on this page. Whether or not a table is sortable, information should no be sorted randomly by default. These edits are not constructive and will be reverted. Filetime (talk) 00:29, 4 March 2022 (UTC)

Fluoride

Hi Smokefoot. I'm completely disinterested in whether fluoride batteries should be in the Fluoride article. But if you are going to remove the details could you make sure to not cause cite errors. You've twice removed not just details of the batteries, but also part of the preceding cite. Thanks LCU ActivelyDisinterested ∆transmission∆ °co-ords° 14:42, 7 March 2022 (UTC)

Apologies for my sloppiness. Won't happen again. Thank you for the careful editing. --Smokefoot (talk) 16:06, 7 March 2022 (UTC)

Polar effects

Nice spot on polar effect. Electron-donating group and Electron withdrawing group (and numerous variant spelling thereof) both link to that page - but they really shouldn't because it's just awful. I briefly thought about repointing them to electronic effect but that is also bad. What in your option would be the correct name for a page about these? --Project Osprey (talk) 16:51, 16 June 2022 (UTC)

Category:Diene complexes has been nominated for merging

Category:Diene complexes has been nominated for merging. A discussion is taking place to decide whether this proposal complies with the categorization guidelines. If you would like to participate in the discussion, you are invited to add your comments at the category's entry on the categories for discussion page. Thank you. –LaundryPizza03 (dc̄) 19:53, 23 June 2022 (UTC)

Novolaks

Hi Smokefoot. You started the article Novolak in 2019. Novolaks are included in the phenol-formaldehyde article. Both articles contain similar information. What is the purpose of a separate Novolak article? Sandcherry (talk) 04:18, 12 July 2022 (UTC)

Drawing

Hi Smokefoot, I used one of your drawings for an article in deWP, and an eagle-eyed reader complained now that you created a four-bond oxygen atom in the lower left corner, maybe you can change that when you get a chance. Thank you. Cheers! --Mister Pommeroy (talk) 15:11, 11 August 2022 (UTC)

@Mister Pommeroy:Thank you! I redrew the whole thing (tedious!) and hopefully error-free.--Smokefoot (talk) 16:54, 11 August 2022 (UTC)

Thanks for the quick (but hopefully not too tedious :-)) support! --Mister Pommeroy (talk) 17:47, 11 August 2022 (UTC)

Biology

Hi Smokefoot. I've added back the IPCC sites to biology as they are required by referencing. At some point someone added short forms refs that require these cites to the Biosphere section, but forgot to added the cites themselves. If you wish to split the Biosphere bisection from the article please do, but the cites need to remain until that is done. -- LCU ActivelyDisinterested ∆transmissions∆ °co-ords° 11:59, 12 August 2022 (UTC)

Your expertise needed

Hello, Smokefoot. You don't know me, but I stumbled on some edits by Herravondure, who I also don't know, involving "de-orphaning" articles. I know nothing about that process, but discovered that you and another editor educated Herravondure on May 2 about those types of edits. But I can see that since then, there have been many edit summaries showing "Successfully de-orphaned!", not to mention the hundreds done prior to your inquiries on the editior's talk page. I just wanted to see if you could review some of Herravondure's de-orphaning edits to determine if they're being done as you instructed. I thought I should let you know in order to prevent an ongoing problem. Thanks much. Stoarm (talk) 13:51, 14 August 2022 (UTC)

Back in May, User:Herravondure did not contribute in ways that I would recommend, but in recent months that editor has desisted from mainstream chemistry and applications of chemistry, which are my focus. Wikipedia is so sprawling that I avoid chasing problem editors.

It is my observation that Wikipedia is populated by a lot of seemingly compulsive editors, some of whom may be children, who contribute all sorts of esoteric content because it satisfies some urge even when they really have nothing to contribute. So long as such contributions are super esoteric (i.e., dont matter), such content could go unchecked for years. In any case, you are welcome to take up the User:Herravondure predicament with other editors. Cheers, --Smokefoot (talk) 14:27, 14 August 2022 (UTC)

Makes sense. In any case, thanks for the great work I see you're doing for this project. Wikipedia needs a lot more editors like you. By the way, the circumstances surrounding the Surreal Barnstar you received this past October made me chuckle. Well done. Stoarm (talk) 14:46, 14 August 2022 (UTC)

Selenosulfide vs Thioselenide

Hello, you've recently created selenosulfide but we also have thioselenide which seems to be the same thing by another name. Project Osprey (talk) 12:55, 18 August 2022 (UTC)

Yikes! I will deal with this oversight. Thank you, --Smokefoot (talk) 12:57, 18 August 2022 (UTC)

Xylan Wikipedia page

Hello, I am new to Wikipedia. I recently completed a PhD on xylan chemistry and made some edits to the Wikipedia page. I am not sure why you removed the references I added. Can you let me know so I can keep it in mind for next time I edit an article? Thanks, Amanda Xylhail (talk) 19:06, 15 September 2022 (UTC)

@Xylhail: Hi Amanda: Having a PhD in Chem is convenient for contributing to Wikipedia Chem. Also important are knowledge of guidelines (see WP:NOT, WP:COI (dont cite your pals) and WP:SECONDARY (cite general sources) And most important is perspective, which is not conferred with the PhD.

So consider this: 26396 publications discuss xylan. Should we aim to cite all of them? Or, maybe we should focus on the 13,733 papers that have appeared in the preceding decade. That comes to about what? 3-4 papers EACH DAY. Is that what you recommend? Suddenly it becomes apparent that one's precious paper is afloat an ocean of other precious, super-insightful papers. So, excusing my tone, you can now appreciate the situation here. Bottom line, cite books and major reviews. And if you are indeed smart, contribute to topics slightly outside of your thesis work. Thanks for asking.--Smokefoot (talk) 20:43, 15 September 2022 (UTC)

Protection of page P-Anisidine to prevent Wikipedia:Vandalism

Smokefoot, hello!

Could you protect page P-Anisidine to prevent vandalism?

85.109.136.232 (talk) 14:54, 27 September 2022 (UTC)

Please talk to your parents or your teacher before editing on topics where you are unfamiliar. --Smokefoot (talk) 15:28, 27 September 2022 (UTC)

That IP is having a bit of a time-out (but I also protected that page to prevent ongoing disruption there--thanks to them for calling attention to the problem there. DMacks (talk) 18:52, 27 September 2022 (UTC)

Diborane smell

For better logic and clarity should not the diborane description:

It is a toxic, colorless, and pyrophoric gas with a repulsively sweet odor.

be changed to:

It is a toxic, colorless, and pyrophoric gas whose combustion products have a repulsively sweet odor.

I see that details of the combustion products are farther down the page. I should not make the change, because my chemistry knowledge is poor wondering if there is some accepted convention for this omission. Years ago I did "dispose" of 1 cc of diborane with a bb-gun, and the explosion turned heads from hundreds of feet away. I was not downwind. Jslipscomb (talk) 17:00, 27 September 2022 (UTC)

Well useful comment, accepted with much gratitude. And a wonderful story. Lucky you. The actual species perceived by smell is an old but obscure debate. Do we smell the molecule or the molecule after it has partially or fully hydrolyzed or oxidized or both (plus the smell of the other oxidation/hydrolysis products). So the convention is usually (I dont really know for sure): we just report what people say (and in the case of diborane, that they dont retest your experiment). The other practical matter is that we cant report personal observations as fact. Cheers, --Smokefoot (talk) 17:53, 27 September 2022 (UTC)

Thank you sir. Story of the blast (mixed with 5 cc pentaborane, which takes a second to burn so flamethrower) at Air Rifle. Yes, in some ways my high school years were cool. Jslipscomb (talk) 01:53, 28 September 2022 (UTC)