User talk:~K

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Welcome to the Wikipedia

I noticed you were new, and wanted to share some links I thought useful:

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Sam Spade Apply now, exciting opportunities available at Spade & Archer! 15:05, 14 Apr 2005 (UTC)

Reaction scheme template, Chemistry Wikiproject

Hi,

I'm Martin Walker, another chemist posting on Wikipedia, and I've been following your contributions- they are very much appreciated! I notice that you have been writing a lot of reaction pages, and you have posted a "posting template" on your user page. This brings two things to mind:

1. I have around 40-50 images of reactions which are currently NOT posted anywhere except the compound pages- the zinc chloride page for example has lots! I have refrained from posting these to a general "reactions" location simply because if we have 200 chem reactions and each has 3 examples (not unlikely 2 or even 1 year(s) from now) these simple categories will be swamped. I have the Commons reactions category bookmarked, but although this has only been going a short while it is already very slow to load. Do we need to create "articles" within this category to group things together, or should we start subcategories- acid-base, redox, etc? This relates to the categories vs. article debate on Commons. I suspect that this category may become almost unusable as a resource by the end of the year (unless I'm missing something, which I often do!). What do you think we should do? Once we can resolve this, I'll try and upload my rxn schemes for general use.

1. Can we recruit you into Wikipedia:WikiProject_Chemistry, and possibly also Wikipedia:WikiProject_Chemicals? There has been a resurgence of interest in these, and the chemicals project (which writes pages on compounds) has been particularly active, with some of the activity associated with getting Hydrochloric acid onto the main page earlier this week. I suspect you probably have ideas on how to write good reaction pages by now- do you think we should have some standard guidelines? Should we have a new Wikiproject devoted just to reactions? Join us and let us know what you think!

Thanks, Walkerma 16:09, 29 Apr 2005 (UTC)

Hello. Thank you for taking an interest in my work here. You've said much, and I have just as many questions. My current plan is to expand the number and scope of the pages on organic reagents, organic reactions, and pharmaceutical drugs. I feel relatively new to Wikipedia, so I really don't understand your second question. What is the difference between what I plan on doing and joining the WikiProject_Chemistry? What does it mean to join the project? What would be expected of me? I apologize for the lack of understanding in this area, but don't let my newbie-ness frighten you. I'm interested in joining, I just don't know what that means.

As for your first question, I agree with you in that the 'chemical reactions' and 'chemical structures' pages are becoming to large to handle. I would favor creating sub-categories because it preserves the heirarchical nature and gives the ability to generate further sub-categories. If you can set up some sub-categories, I'll help you move the images around.

Personally, I look forward to when I can use the Wikipedia as a reference for advanced organic synthesis and drug design. I realize the Wikipedia may never reach that level, but I'm hopeful it will (and maybe even in my lifetime).~K 05:15, 30 Apr 2005 (UTC)

I am still a bit of a newbie myself- you just taught me that useful way of linking from the Commons using "w"! Regarding the categories, I have created some new sub categories in the Commons. I did this by uploading a file with a non-existent category link in it, then I clicked on the red link to write a brief header. My files are scans and don't look as pretty as yours, but they serve to start the cats off. I have made three initial subcats- organic, inorganic and organometallic. I didn't do any biochem cats because it's not my area. Then within organic I created two subcats- functional group interconversions and C-C bond formations; we could consider other ways to split it, but at least it's a start.

Regarding the Wikiproject, this provides a way of coordinating several people's work. A good example of a successful project is the elements project, which led to a standard, well-written page for every one of the significant chemical elements. Two (Helium and Titanium) even made featured article status. One person said "I'll write this" while someone else said "I'll write that", someone else donated the pictures, and within a few months they had an impressive set of pages. By comparison, the reaction pages and chemical compounds are rather random- but we plan to change that. We have a set of goals and lists, and we are working away at the lists- you can see how we are doing at Wikipedia:WikiProject_Chemicals/Organization. I recently added your triphenylphosphine contribution, I was about to start work on that when I noticed that you had beaten me to it! The idea is that if we can coordinate things then we don't duplicate each others work, and we end up with a balanced set of pages (that's what the idea of the goals was). We also try to finish things, not just leave things as stubs. Since the contributors can also shape what they work on, you should be able to keep on enjoying your contributions, but you can also see it as part of a bigger effort to raise up the chemistry pages to a higher level. The Chemicals wikiproject is more active right now, but I think once we have reached our goals people may well want to work on reactions, which I can see interest you. As I see it, you need a good infrastructure of compounds like aluminium chloride (surprisingly a rel. new page) before you can write a really good article on reactions like (say) Friedel-Crafts acylation. We would probably just ask you to pick a handful of compounds you like (from the list, or add your own) to write over the coming months.

I agree with your vision of Wikipedia for the long term- though many Wikipedians would probably shudder at the thought! The current emphasis is on making pages understandable for the non-expert; I'm in education so that is a natural emphasis for me, though I confess I get a bit technical sometimes. However I also think that a 14 year old accessing a page like Sonogashira coupling should not expect to have terms like liquid, temperature or even solvent explained, but these sorts of things should be explained in a basic page on (say) Redox reactions. In other words, I believe that in the dark corners of Wikipedia like dysprosium(III) chloride it's OK to be more technical, but when I was editing alcohol recently I tried to be more basic. I also try to "layer" my articles such as cobalt(II) chloride- you can get some good things out of it for your high school project, yet even someone more advanced like yourself would still find it useful. I think once there are a large number of pages of this type on reactions, compounds and chemical concepts, then chemists will naturally gravitate to using Wikipedia as a reference tool. I have no doubt that parallel things are happening in physics, psychology and many other fields, and good luck to them. Walkerma 20:01, 30 Apr 2005 (UTC)

PS: Sorry to make this even longer, but I would suggest you sign up for the Wikipedia:WikiProject_Chemicals and contribute to the 50 reagent pages. Pick a few and let us know which ones, on Wikipedia_talk:WikiProject_Chemicals. Cheers, Walkerma 20:24, 30 Apr 2005 (UTC)

Response to Tetramethylsilane and trimethylsilyl remark

See my response to your remark on "Tetramethylsilane and trimethylsilyl" at the bottom of my talk page. H Padleckas Talk 05:19, 2 Jun 2005 (UTC)

Format for references

Since you mentioned that you were (possibly) starting to work on a style guide for chemistry, I wanted to see your opinions on format. I notice that you recently switched the format of some references in Wittig reaction to ACS style- I don't have a problem with that, I wrote them in my "standard" style then noticed that the earlier ones were in another format. Which format do you think we should recommend, or should there be a couple of allowed systems, or is it "anything goes"? Personally I don't like the ACS system of YEAR, Vol, pages, but I have to admit that it is becoming standard- even Elsevier journals seem to be using it now. RSC has their own system, but it is similar to ACS. I personally prefer the system I was trained with of Vol, pages (YEAR), but this is less common than it used to be now that journals like Tetrahedron have switched to the American format. It is still common in books, for example the "Synthetic Methods" series from Thieme uses it- that's why I stuck with using it. I am also aware that a physicist or biologist submitting references will have their own style (see copper(I) oxide, for example)

I think we should probably have a recommended format in our guidelines- one that we agree on. I would suggest that the ACS Style Guide would be a great place to start when designing guidelines (notwithstanding my opinions on reference layout!). What do you think?

Cheers, Walkerma 17:58, 3 Jun 2005 (UTC)

I have to admit that I was "raised" on the ACS style, and am a little baised in its favor. I agree that we should have a recommended format for references. Wikipedia must already have a recommended format for references, but I must (shamefully) admit that I haven't looked into what it is.

When designing guidelines, I believe the best place to start is Wikipedia. (Just to retain the homogeneous look and feel across pages.) The next place to look is the ACS Style Guide. After that, I don't know.

I haven't begun work yet on the actual style guide. This weekend, my goal is to outline goals for this style guide and post them on the WikiProject Chemistry talk page. After a week of comments, maybe we can actually start writting the guide. The reason for posting in WikiProject Chemistry first is get a common understanding with folks, especially Wim van Dorst who seems against the idea.

~K 19:39, 3 Jun 2005 (UTC)

Chemical Formulae/Reaction Graphics

I noticed you created some chemical reaction graphics. You put on the description page it was made with ChemDraw and Gimp. Is there anything like this for Windows that can create neat graphics easily? At the moment i'm just using Fireworks to 'manually' create grpahics. Thanks. Borb 22:17, 16 Jun 2005 (UTC)

Hey Borb, I actually use ChemDraw and the GIMP on WinXP. If you do not have access to ChemDraw, then I suggest you download the free version of ISIS/Draw by MDL. Walkerma has had good success creating images with ISIS/Draw. I don't know how he does it, so you should probably ask him about the details.

If you just need a few images, and don't mind waiting a few days for me to draw them, just tell me which images you want and I'll deposit them in the WikiCommons.

~K 01:57, 18 Jun 2005 (UTC)

Thanks. I will give ISIS/Draw a try. I didn't realise chemdraw was a commercial product. I thought it was a plugin for gimp or something. On passing, please can you look at my comment at Category talk:Functional groups. I think I put it in the wrong place and no one will see it. I am trying to make wikipedia chemistry better at the moment but it needs a hell of a lot of work it seems. Anyway, thanks

Borb 18:35, 20 Jun 2005 (UTC)

Borb, A great way to help improve the quality of chemistry articles is to join WikiProject Chemistry and/or WikiProject Chemicals so we can all coordinate our activities. WikiProject Chemicals is VERY active right now, and I'm sure that you can get some great feedback quickly. ~K 15:48, 21 Jun 2005 (UTC)

Chemistry history

Hi ~K, I saw here how you deftly inserted some references to a compound to reflect its chemical history. What is your data source? Could I occasionally ask you for more references? Pharmacological history is quite poorly covered (in sildenafil, Nick Terrett is not mentioned, nor is UK-92,480 and Simon Campbell and David Roberts). Could we start with nimodipineJFW | T@lk 28 June 2005 20:30 (UTC)

Hello JFW, I don't remember exactly, but I do believe that these references (and the structure) were found in the Merck Index. I added a reference to sildenafil you might like. Regarding pharmacological history, my knowledge is very spotty. I'll contribute where I can. The pre-clinical history of drugs is closely guarded by pharmaceutical companies. They typically believe that revealing too much info can lead to me-too drugs. Some of it can be pieced together by reading the original research articles, but the interesting details are rarely included. Anyway, I'll bring the Merck Index home from work for the long weekend and I'll add some new info to articles.

By the way, the latest issue of Chemical and Engineering News has quite a lot of information on the 'Top 50' pharmaceuticals of the modern age. (About a page per drug.) This should help alot with some pharmacological background.

~K 29 June 2005 02:31 (UTC)

Thanks! How do I get hold of Chem Engin News? JFW | T@lk 29 June 2005 10:15 (UTC)

My local library has a subscription. Otherwise, check out a university chemistry library. The beginning of the article is here. ~K 29 June 2005 16:24 (UTC)

Great! The whole issue is available online! JFW | T@lk 30 June 2005 11:11 (UTC)

Category:Medicinal chemistry

Should the parent category not be biochemistry? Mel Etitis (Μελ Ετητης) 3 July 2005 20:46 (UTC)

Definitely not. Biochemistry and many other fields play a role in the design of new drugs, but organic chemistry plays the largest role with the synthesis of the new pharmaceuticals. Another way to put it: Medicinal chemists are in the Chemistry Deparment, not the Biology Department.

I don't mean to stir things up with my category edit. If there was a better way for me to change the category, please tell me as I still feel new here. ~K 4 July 2005 05:28 (UTC)

Leimgruber-Batcho indole synthesis

Hi K, Can you fix the second step in this scheme to show the hydrazine hydrate? Also I would recommend writing out the word Raney in full, someone less knowledgable might get the idea that radium was used! This reaction is an old friend, I worked on it in the lab then we did a pilot scale run (5 kg or so) in 1985 or so, my former employer used to manufacture DMFDMA. Please check my additional content for errors and feel free to make changes- I feel like you and I are good proofreaders of each others work! Cheers, Walkerma 00:31, 17 July 2005 (UTC)

Good points. I'll fix the image right now. Thanks for all the double-checking and help. I really appreciate it. ~K 01:15, 17 July 2005 (UTC)

Ethanol links

Removing a valid external URL link to a site that refute's Dr. Pimental's flawed analysis on the energy efficiency of ethanol appears that you have a political bias.

http://www.ncga.com/ethanol/debunking/index.htm

But you left the external link to a flawed analysis. Are you letting your bias show?

I apologize for not catching and deleting the Pimentel study link also. Ethanol is a discussion about the molecule. I move both links (and named them rather well I may say) to alcohol fuel where they belong.

If you want someone to take your edits seriously, and not immediately think they are linkspam, then you should register and get a user account. ~K 02:25, 26 July 2005 (UTC)

footnotes

Hi K

I noticed that you have modified the footnotes in the Tishchenko reaction, i suspect this is the official way to do this and i respect that but on my screen the 1's and 2's look miserably small and the references themselves are not numbered. is that just my screen or is there anyway around this?

PS I utterly dislike stubs and i could not help myself re-editing DABCO

Hello V8rik, I've used Firefox for so long, I've forgotten how different things can look in IE. I looked at the page in IE and you're right: The footnotes are painfully small. I can only suggest two things: 1) increase the font size (View->Text Size) or 2) get a different browser. I recommend Firefox, but any standards compliant browser will work well.

Regarding the footnotes themselves, they are just ways of hyperlinking the articles. There's a HUGE discussion going on at Wikipedia:Footnotes and the technique I've used was found on Wikipedia:Footnote3. Maybe you should ask there about better IE workarounds. (I just perused the talk page and found that Wikipedia_talk:Footnote3#Illegible is exactly what you're looking for because others are having the exact same problem.)

The reason for including the stub notice on DABCO was to have it listed in the stub listing. Also, when people see the stub notice they know that the subject is woefully incomplete, which I think is rather helpful to someone completely outside of that specific field. I would recommend putting it back to encourage others to contribute to the page.

Also, don't forget to sign your messages with the four tildes (~~~~)

I hope I was at least a little helpful. ~K 00:50, 1 August 2005 (UTC)

Wittig reaction

Hi K,

I have finished uploading my contribution to the Wittig page. Do you think it is complete now, or is there anything still missing? I'd appreciate it also if you can find the missing group from my latest reaction scheme! The only problem that seems to remain (that I can see!) is with printing- if you print the page from IE it's a mess, and if you do it from Firefox it's an absolute disaster (it crashed Firefox twice exiting from Print Preview). A lot of the problem of course is caused by the fact the Firefox can't handle images well, but do you know of anything we can do to improve things? I tried to make things more compact in the later part of the page, and I think it now looks great on screen (though if you disagree please edit) - but it's hard to get a neat printout. Thanks, Walkerma 05:31, 3 August 2005 (UTC)

You must have hid your error well, because I can't find any. :) I think the page looks very nice indeed. The page is definitely complete. However, there are more things we could add. (I like your opinion as to whether we should add them.) What I'm thinking of are reactions that form Wittig intermediates. For example, the reaction of an epoxide with a phosphine generates an alkene via the betaine. It's not a wittig reaction, but uses a very similar mechanism. I'm sure there are others, but they aren't coming to mind right now.

I'd never thought about the printing errors/problems until you mentioned it. I tried it out, and you're right: Print Preview and the final printed page are awful. I tried moving the images around the page, but that didn't fix anything. I searched the Wikipedia in case someone else has mentioned this problem before, but didn't find anything. I think this is a perfect question for the Wikipedia:Village pump (technical). ~K 15:48, 3 August 2005 (UTC)K,

Thanks for the suggestion of the Village pump, I have posted a comment there. As for the reactions you mention, these are definitely not the Wittig reaction and so IMHO they belong in a "see also" along with the HWE reaction etc. We can certainly Wikilink, but I think something like epoxide/R3P rxns should be on a separate page. Thanks again, Walkerma 16:26, 3 August 2005 (UTC)

Science pearls

Hello,

Since you contributed in the past to the publications’ lists, I thought that you might be interested in this new project. I’ll be glad if you will continue contributing. Thanks,APH 10:45, 11 September 2005 (UTC)

Hello APH, I will contribute, but since I don't have much WikiEnergy lately, I think that I will not join the project right now. ~K 16:26, 11 September 2005 (UTC)

I'll wait ;-) APH 07:42, 12 September 2005 (UTC)

MDL ISIS

Thanks for uploading the sildenafil image. I'm having trouble with MDL ISIS 2.5. Do you use it? It's not exporting! JFW | T@lk 17:10, 26 September 2005 (UTC)

You're welcome for the image. Unfortunately for you, I use ChemDraw to create TIFF files and The GIMP to convert the TIFF into a PNG file. This works REALLY well, because (for some reason) the TIFF image is quite large, leading to a nice looking, high-resolution, black and white PNG file. I have access to MDL ISIS-Draw 2.5 and find it much more difficult to use. But it does export to TIFF format, so maybe you should try that. Unfortunately, I can't help you beyond that. If your copy of ISIS-Draw is not exporting to TIFF, maybe you should reinstall it or get something different. I hope this helps. ~K 19:20, 26 September 2005 (UTC)

I hope you don't mind me butting in, I've been using Isis 2.4 for a while on Wikipedia, as I have used Isis for years in my work. This version can't export to TIFF, so I print it out on a laser printer, then scan it in at 600 dpi, then shrink it down in Irfan View to the right size, save it as PNG or GIF. You can see an example of what it looks like here. Walkerma 20:24, 26 September 2005 (UTC)

Walkerma, your comments are always welcome here. I'm even more impressed with the image now that I know you went through hell to get it on the Wikipedia. You should upgrade to ISIS-Draw 2.5, because you can export directly to TIFF. Just my two bits... ~K 03:20, 27 September 2005 (UTC)

RfA thanks

Thank-you for expressing your confidence in me at my recent Request for Adminship. The final result was 40/0/0, and my "superpowers" have now been activated. I look forward to helping out with the development of the encyclopedia. Physchim62 (talk • contribs)

Med chemist

it says you're a med chemist. would you mind if i asked what your chemistry background is? i'm curious about who contributes to wikipedia. good work, btw. Eugene Kwan 06:31, 16 December 2005 (UTC)

Hello Eugene, I got my PhD from an ivy league school and have been working at pharmaceutical companies for several years. I find industry very unaccepting when it comes to contributing to Wikipedia, so I prefer to remain anonymous. Of course, I enjoy contributing to the Wiki. Someday, I think the Wikipedia will become a world-class chemistry reference. Of course, to get there we will need a lot of contributors like yourself.

I see that you are studying with David Evans. That sounds very exciting. I presume that you are working on some enormous natural product with very difficult stereospecific transformations. Whatever it is, best of luck, and I hope your synthesis makes it into Classics in Total Synthesis III ~K 07:13, 16 December 2005 (UTC)

Thanks for the kind comments. I completely understand your desire for anonymity. Actually, I'm working on methodology for the intramolecular Michael addition reaction. But I may end up doing synthesis in the future. It's very exciting working here. I guess I couldn't leave the aldol page in that condition, what with working with Dave and all. Eugene Kwan 09:04, 17 December 2005 (UTC)

good work on the wittig reaction there. i find the whole thing very confusing... Eugene Kwan 03:57, 19 December 2005 (UTC)

ylide

Sorry about incorrectly changing the spelling of ylide to ylid. I had been reading Organic Chemistry by Clayden, Greeves, Warren and Wothers and it says ylid in there. However a quick check on google shows that almost everyone else uses ylide! Apologies Ollie 04:04, 29 December 2005 (UTC)

No problem. ~K 16:09, 29 December 2005 (UTC)

List of Chem books

Thanks for your comments on the list of chem books talk page. The more people we get to comment the more it covers the whole of chemistry and the more NPOV it can be. I'm not in Med Chem although I'm on the fringe doing some computational chemistry with a couple of guys in the Dept of Med Chem at Monash Uni. The book on Med Chem that you added - how does it differ from "Introduction to Medicinal Chemistry" by Alex Gringauz, Wiley-VCH 1997, which for obscure reasons I have on my shelf, or indeed any other book that covers Med Chem? Obviously you know more about Med Chem than I do. I'm happy to follow your opinion but I would like some reasons that suggest that we are being NPOV or at least not seriously POV. Best wishes, Bduke 03:04, 11 January 2006 (UTC)

I'm not familiar with the Gringauz book you mention. However, the Wermuth book I added is different from most other medicinal chemistry reference books. Most med chem books (Ex: Goodman and Gilman) devote a chapter to each major drug class/indication. (Diuretics, local anesthetics, general anesthetics, etc.) The Wermuth book does not discuss any drug classes, but instead discusses how to discover and develop a pharmaceutical drug. (Ex: structure-activity relationships, methods of finding leads, techniques for lead optimization, QSAR, COMFA, etc.) I believe the med chem student and professional would find this book immensely helpful. I hope this helps. ~K 03:23, 11 January 2006 (UTC)

References

It is quite neat, isn't it? You can find the description of the new trick at m:Cite.php. What that page doesn't tell you is that once you define a reference you can call it again using <ref name="foo" /> (a self closing tag). Hope this helps. Cheers! -- Rune Welsh | ταλκ 05:18, 26 January 2006 (UTC)

Thanks a ton. ~K 05:23, 26 January 2006 (UTC)

Raney nickel

I replied to your concern on the article's talk page already, so I'd appreciate if you had a look. Also I think it would have been nicer if you had commented on the talk page before removing the material. Thanks. -- Rune Welsh | ταλκ 20:02, 29 January 2006 (UTC)

Quite disruptive indeed you were, adding all those references and expanding the safety section. I don't think I'll be ready to forgive you just yet... :-) Thanks! -- Rune Welsh | ταλκ 16:06, 31 January 2006 (UTC)

Corey picture

Hi K,

I notice that your (very nice) Corey picture has a "copyright violation" tag on it: http://commons.wikimedia.org/wiki/Image:EliasJamesCorey.gif

Can you fix this, or will it have to be deleted?

Thanks, Walkerma 21:17, 30 March 2006 (UTC)

Oops. Thanks for bringing this to my attention. I guess I made an error and it will have to be deleted. I'll start looking for a free Corey photo. If you have one then please change the images. ~K 16:02, 31 March 2006 (UTC)

Backdraft

I reverted your edit on the article Backdraft. While it is arguable whether or not a backdraft is part of chemical reaction, it is innapropriate to remove a stub. If you feel the stub template is innacurate, please replace it with a better stub instead of simply removing it.--Oni Ookami Alfador^Talk|@ 07:10, 6 April 2006 (UTC)

O.K. I'll change it. ~K 14:49, 6 April 2006 (UTC)

Clotrimazole structure image

Hi there, a while ago you uploaded the image commons:Image:Clotrimazole structure.png to the Commons. Now, another user has uploaded an additional image commons:Image:Clotrimazol Synthesis.png showing the synthesis of this compound. If you have some time, could you modify the new image so that is in line with your image regarding drawing style? For example, the lines in the new image are much thinner than in your image, the typesetting of the letters is different and so on. Both images are used in the German article about Clotrimazole, so it would be nice if they would look uniform. Best Regards, --Uwe 10:23, 3 May 2006 (UTC)

Please read: Copyright notice SPAM on QSAR page?

Please read: discussion JKW 16:57, 6 May 2006 (UTC)

Grignards

The grignard article has been going too organic, what about reactions such as the formation of PhB(OH)2 and PhSnBu3. These are very important reactions in organometallic chemistry which dare I say might end up being used as reagents in organic chemistry. I think that a cat for carbon-heteroatom forming reactions is needed.Cadmium

Good idea. The article should have as many categories as is appropriate, and a carbon-heteroatom forming reactions category is also appropriate. ~K 21:08, 5 August 2006 (UTC)

Sadly I have no idea of how to create a new categorie, please tell me how it can be done.Cadmium

It's super easy. On the Grignard reaction page, just edit the article to include your new category. After you save the page, you will notice the category will be a red link. Click on that new red-link category and it will let you "edit" the category page. All you really need to do is include a pre-existing category that will serve as your new category's parent. Good luck. ~K 22:03, 5 August 2006 (UTC)

Thanks for fixing the link between categories.Cadmium 20:05, 7 August 2006 (UTC)

IG Farben building

Hi K, since you maintain the Featured article on the portal, you might be interested to know that IG Farben Building is an FA, it was obviously the HQ of IG Farben (and also Allied forces after WW2). So if you are running out of pure chemistry FAs, you might consider it. Of course, we could always get to work on making the Lavoisier article an FA.... Walkerma 21:29, 23 September 2006 (UTC)

I haven't considered going outside the domain of chemistry to find related articles. It's a good idea. ~K 00:06, 24 September 2006 (UTC)