Wikipedia talk:WikiProject Chemistry/Archive 3

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POV changes?

A user recently made a bunch of changes to Matrix-assisted laser desorption/ionization, Koichi Tanaka and Mass spectrometry - Special:Contributions&target=195.186.157.218 - that may be pushing a POV. I assunme the partipants in this WikiProject know something about chemistry, which is a lot more than I do. Please validate those changes. Josh Parris # 20:28, 1 November 2005 (UTC)

Diffs:
See:
I have changed m/q back to m/z, and wikified and reworded some passages. Mass spectrum should be improved. Cacycle 23:27, 1 November 2005 (UTC)

Letter in C&E News

In the latest issue of Chemical and Engineering News, there is a letter (page 6) with the title, "Taking a page from Wikipedia". It proposes that chemists should have a resource like Wikipedia, to provide peer review for feedback on synthetic procedures, including negative results. It might also provide a central place for review articles on important topics, allowing the review article to stay up-to-date. It sounds a very sensible yet visionary idea to me. The author (Matthew Stone, Oxford, England) calls on the ACS to "invest its prestige, experience, and resources to implement sucha Wikipedia-style updatable database.." Thoughts, anyone? Should we approach ACS as a WikiProject? Walkerma 16:55, 22 November 2005 (UTC)

I'd be interested to help out, even draft up a letter for that. However, in what capacity do we want to approach them? As a way to get a word out that Wikipedia would be most grateful if some experts in the field of chemistry would contribute to our articles? --HappyCamper 01:11, 23 November 2005 (UTC)
  • In my not so humble opinion, several experts in the field of chemistry are already contributing to our articles. Wim van Dorst 23:15, 23 November 2005 (UTC).

I was thinking that we might want to offer to help with the design of such as aystem, we have seen what works and what doesn't. We could possibly approach them directly rather than through the letters page- I am quite active in ACS and I dare say some others are too, so we have contacts. I am also interested to know reactions of people in this project to the letter, and what they think would work well as a Wiki. Walkerma 03:15, 23 November 2005 (UTC)

So, basically, we would be approaching them in the following way: "We're a group of Wikipedians who have been contributing to Wikipedia for a while and would like to share our expertise and experience with the chemistry community at large regarding the benefits of using Wiki-related technology for coordinating research projects..."? --HappyCamper 03:21, 23 November 2005 (UTC)

As you say, except that doesn't mention our chemistry focus. I think the fact that we already have a cohesive group of chemists with Wiki experience means we have something useful to offer, if they're interested. Chemistry has its own specific foibles and problems, only chemists fully appreciate that. Walkerma 04:01, 23 November 2005 (UTC)

Hm...well, what do you think should be the next step then? --HappyCamper 04:13, 23 November 2005 (UTC)

My guess is that at least the folks at C&E News liked the idea, and ACS is open to it. I'd like to get comments from several project members, once they have had a chance to read the original letter. If people are interested, I could contact people in ACS directly as a representative of the project, and present whatever people think is appropriate. I am hoping to present something on Wikipedia to the chemical information folks at an ACS conference, if that works out that may also be a good venue to raise the topic. Walkerma 04:20, 23 November 2005 (UTC)

I should say, if there are others (HappyCamper?) here who have better contacts at ACS than me I'd love for them to take the initiative on this. I only suggested that I could do it, assuming that others aren't interested/able (eg our many Europeans). Walkerma 04:25, 23 November 2005 (UTC)

Martin, I think your idea is excellent. I would like to help. To summarize for everyone else, Matthew Stone is suggesting a Wiki that offers the posting and editing of topics such as:
1) Peer-reviewed procedures
2) Up-to-date collaborative research reviews
3) Peer-reviewed techniques
Assuming these goals, I believe the Wikipedia is neither adequate nor appropriate. It is not adequate because such a chemistry-intensive wiki would have to have some sort of structure drawing/displaying software readily available. (If you haven't noticed, it's quite difficult to draw a structure or scheme in an article.) Wikipedia is not appropriate because it's an encyclopedia, not a reaction database.
However, Wikipedia is an excellent place for goal #2. That is something that we can work on right now, right here.
A good secondary goal for working with the ACS would be to encourage more chemists to become Wikipedians.
~K 05:46, 23 November 2005 (UTC)

Reading the overall idea, I understand that the proposal is to have an ACS Wiki website (similar to Wikipedia) for doing the things that the ACS does. And that is a good proposal. But I don't see the ACS (or any other chemicals society) as an organization contributing to Wikipedia. They may recommend to they chemists members to have a look at Wikipedia (notably these Chemistry and Chemicals WikiProjects) and suggest that they too contribute. Wim van Dorst 23:15, 23 November 2005 (UTC).

That's true. At least for me, I'll keep this in the back of my head and follow up with it whenever I get a chance to. --HappyCamper 13:39, 26 November 2005 (UTC)

New article

I have created article: Valency number. I am fairly suprised that noone has previously created it! Valence number re-directs to it. I have also added a link to this article on the Chemistry article under "See also". --Kilo-Lima 19:11, 30 November 2005 (UTC)

The explanation for this may be due to different usages in English, the normal term I have heard for this concept is the single word "valency," which already has an article. Can you check the valency article? If it means the same thing, then the two may need to be merged. I've learnt (the hard way!) that it is often good to check the alphabetical index of articles to see if someone has written an article with a similar (but not identical) name to the one I'm writing. Walkerma 20:09, 30 November 2005 (UTC)
I wish I had checked this page before doing major expansion and reconstruction to Kilo-Lima's Valence articles (chalk one up to learnin the hard way). While valency does mean the same subject as valence number, IUPAC regards valence number as the most correct term. Oxidative State refers to electronic configuration and spin as well as distribution, so while all elements have one valence value they can have multiple oxidative states (albeit not at the same time).Das Nerd 00:21, 1 December 2005 (UTC)
Thanks anyway, hopefully we can incorporate some of your input if we merge the articles. However, surely elements can have multiple valencies (or should I say valence numbers?)? For example can't carbon have a valence no. of 4 in carbon tetrachloride but 2 in dichlorocarbene? Do you have the IUPAC reference, it may guide us regarding a possible merge of the two articles, and it should be in the article anyway. Thanks Walkerma 04:48, 1 December 2005 (UTC)

The IUPAC reference is here, to valence! It does imply that an element can only have a single valence. IMHO such a terminological mess is worthy of a Wikipedia article! Physchim62 (talk) 10:49, 1 December 2005 (UTC)

I should say that we obviously need a merge here, with lots of redirects. I am currently in the same position with Standard electrode potential and various other articles which have appeared to give virtually the same information. Please feel free to discuss the merge here; if there are problems, I will use my superpowers as justified. Physchim62 (talk) 13:54, 2 December 2005 (UTC)
Yes. An admin will have to do it becuase WP needs it for copyright reasons; and it has a history. --Kilo-Lima 16:22, 27 December 2005 (UTC)

Aluminium amalgam

Please see Wikipedia:Articles_for_creation#Aluminium_Amalgam for an article request based on the German Wikipedia article. Can someone provide sources? Also, this appears to be machine translated, so I would appreciate a human translation of the material as well. Especially the last few lines, as I can't translate those myself. I can't seem to get the link between quicksilver and airplanes. - Mgm|(talk) 12:26, 14 December 2005 (UTC)

Nature peer review

As you may have already heard, the scientific journal Nature has peer reviewed 50 scientific articles for factual accuracy. (See Wikipedia:External_peer_review#Nature) Several of the articles were chemistry related such as Dmitry Mendeleev, Robert Burns Woodward and aldol reaction. Let's work put some effort into making these articles more factually correct. ~K 04:31, 15 December 2005 (UTC)

Let us also be grateful for the fact that Nature takes us seriously enough to do the study! But yes, an inaccurate encyclopedia is worse than useless... Physchim62 (talk) 15:45, 15 December 2005 (UTC)
FYI, The Nature website gives this story, which was reported by the BBC here. I will take a look at Mendeleev as I have a suitable book here. I have felt for a long time that aldol reaction was a bit embarrassing; it was much improved by V8rik though, see how it looked 9 months ago! Still needs a lot of work- the harvest is great, the workers are few... Ethanol had 5 errors, we need to look over that. Note that term "error" refers to "factual errors, omissions or misleading statements", I suspect that with the Aldol article there are important things missing. I agree with PC about exposure, though it's scary to think that your work might be scrutinised by one of the world's top science journals! Walkerma 16:34, 15 December 2005 (UTC)
Well, Martin, both you and I accept such scrutiny (though not of our wiki contributions) as one of the conditions for which we draw our real world salaries... We must respond to criticisms, where possible by improving our offer of information. I should mention that the Mendeleev article did not draw any criticism when shown to a group of French school inspectors (personal, non-controlled test, but ironic all the same!) Physchim62 (talk) 17:20, 15 December 2005 (UTC)
I can't work on Mendeleev after all, at least for now, though others are on it. Someone from the Evans group is beefing up the aldol page, I can't think of anyone more qualified on the asymmetric stuff except David Evans himself! Walkerma 05:19, 17 December 2005 (UTC)

Clock reactions

Does anyone feel motivated to write an overview of clock reactions? We have an iodine clock reaction and Old Nassau reaction article but no general article on clock reactions. - Nunh-huh 02:20, 18 December 2005 (UTC)

Referencing in chemistry articles

It seems that the polymer project is growing, and one question was asked there today for which I did not have much of an adequate answer. Could someone take a look and help out? Any help is very much appreciated! (See Wikipedia talk:WikiProject Polymers) --HappyCamper 01:20, 19 December 2005 (UTC)

Collaboration of the month?

As a preliminary to this, I propose a Collaboration of the Month (COTM) to bring some articles up to standard. I suggest a month, because I know the peer review for HCl and HOAc took about 6 weeks, we tend to be very picky! I think I would like to see us start on the main Chemistry article, then consider perhaps some other key general topics like organic chemistry or physical chemistry, but we can debate that. We can put these in our "goals" below, we don't need to have them in our COTM. Please leave comments and suggested topics below.

Comments on collaboration idea

I propose Chemistry for the first one. Walkerma 16:59, 14 November 2005 (UTC)

I believe that a COTM is an excellent idea. I am willing to write the WP:CHEM-COTM page to get us started. Unfortunately, nobody else has chimed in, so I hesitate to start the page for fear that nobody else is interested. If a few more people can comment here, then we can make a decision. ~K 20:05, 7 December 2005 (UTC)
I agree that this is also an excellent idea. What say everyone else? Jawz 08:40, 30 January 2006 (UTC)
I'd go for it. And I second Martin's proposal to nominate Chemistry as the first article we'd focus on. -- Rune Welsh | ταλκ 17:20, 1 February 2006 (UTC)

One compound of the month that is quite timely (and probably Googled often) is hydrogen. The current entry is good, but could be beefed up, esp the energy aspects. So I vote for a compound of the month being element #1.Smokefoot 17:58, 1 February 2006 (UTC)

The elements have traditionally been handled by Wikipedia:WikiProject Elements rather than here, so any work on an element has to be coordinated with them. That group contains a lot of physicists, too. There is a lot of stuff on energy uses such as Hydrogen economy and Hydrogen vehicle, but this is poorly integrated with the hydrogen article at present. Can I take it from this that you're interested in joining a COTW? Walkerma 20:51, 1 February 2006 (UTC)

Goals

Unlike at the chemicals project, the range of articles is much broader here. In my work with WP 1.0 I have noticed that many of the broader WikiProjects are almost inactive for this reason. However I think I would like to suggest we list 30 general topics (e.g., solution), 10 famous chemists (e.g. Robert Burns Woodward) and 10 important chemical reactions or processes (e.g., nucleophilic substitution) and 10 important industrial processes (e.g. Contact process). These goals are modest compared to WP Chemicals, but I expect progress to be slower. I would foresee us setting up a worklist just like the Chemicals worklist. What do others think of this?

Comments on goals idea

  • Even making a short list of lists of goals could be difficult! I would like to see
  • Functional groups
  • Common anions
  • Topics in chemical thermodynamics
  • Analytical methods
  • Fields of chemistry

and that's just for starters! Physchim62 [[User_talk:Physchim62|(talk)]] 09:50, 15 November 2005 (UTC)

UPDATE DECEMBER 5th 2005 I have uploaded some proposed goals and a worklist containing about 150 articles (it's really hard to be comprehensive and do fewer than that). Please leave comments below, and make edits to the worklist. I realise that the articles selected just my own personal choice, but I don't think any of my choices would be at all controversial. If you feel I have omitted something really important (I'm sure I have!) please make edits to the worklist. Of the articles I picked, all but about two articles have been started, and many of them are already at least B-class. However in my research for this I found that many articles on fundamental concepts are either poor or too brief. I think it's about time we set goals for the project to address this, rather than just drifting along. Walkerma 17:20, 5 December 2005 (UTC)

  • My personal interest is more in chemists and chemical history, so I did an initial assessment. It shows that there are twelve chemists all right, but we're missing out on the earlier ones (Middle Ages), and the recent one (20th/21st centuries). I'll try to think of improvements. Or shall we just add (twelve is arbitrary)? Wim van Dorst 21:17, 5 December 2005 (UTC).
  • After completing the whole timeline covering the last 1200 years of chemistry, I have reworded the goal, upping the number to 40 which gives a better coverage of that era. I'm a little low on the last 100 years, though. Any living chemists worthwhile? Wim van Dorst 22:09, 5 December 2005 (UTC).
A good place to start is Nobel Prize winners. ~K 01:02, 6 December 2005 (UTC)
Depending on where you draw the line between the 19th and 20th century, the 20th cent. list is 1-3 names short. E.J. Corey ?? (retrosynthetic analysis) Alfred Werner ?? (coordination theory)
Another opinion of mine is that the beginning of the list is heavily biased to alchemists who were famous as alchemists and mystics (Newton, Flamel) rather than practitioners who were influential on early chemical method (Andreas Libavius, Jan Baptist van Helmont, Agricola). Shimmin 13:24, 6 December 2005 (UTC)

I'm trying hard to keep quiet, on the basis that I've already had more than my fair share included, but I have to agree with Robert Shimmin on this. I don't think we should include alchemists (some I admit I've never heard of!) at the expense of some of the great chemists of the last 200 years. I also think Newton should be administered by the physicists, not by us. Let's exhaust our choices from Category:Nobel Prize in Chemistry winners and List of chemists before we turn elsewhere, I think you'll agree there are some big names missing. Walkerma 16:23, 6 December 2005 (UTC)

  • I added the recommended names (the 20th/21st century part is still short a few), and deleted Newton from the list. Last count up to 15 (well over onethird) where Chemistry Nobel prize winners. For numerical reasons we can't add ALL winners, so we'll have to make a choice there too. And wikilike you're of course invited to add them yourselves to the worklist if you feel like it. Wim van Dorst 23:54, 7 December 2005 (UTC).

A scheme for schemes

In present Wikipedia practice, the usual way to write a scheme or chemical equation, if the structures involved are complex enough that they do not easily reduce to text, is to upload the entire scheme or equation as a single image. This works, but it does not support much image reuse.

There are advantages to representing schemes as tables of images, where each structure gets its own image. Off the top of my head, some of these advantages are:

  • The scheme is somewhat editable
  • The images can be used in other schemes
  • By including a redirect on the image page, clicking on part of the scheme will link to the article for the compound clicked on
  • Each image in the scheme can have its own alt text, so hovering over part of the scheme could pop an explanatory note relevant to that location

In order to look good, however, the component images will have to be visually compatible with one another. This, combined with the usefulness of putting redirects on the image pages (noted above), which might be more annoying than useful if those images are used outside schemes, suggests that it would be good if the component images were somehow marked as being primarily intended for use in chemical diagrams, perhaps with some prefix in the filename; e.g., sch-acetic_acid.png chem-acetic_acid.png rgt-acetic_acid.png, or somesuch.

Also, in order for diverse editors to produce visually compatible images, there must exist some agreement on what the "standard" image appearance is. I think resizing will be inconvenient in this context; rather, it would be better to simply agree on matters like standard bond length, line thickness, symbol font. etc.

E.g.:

Benzene Hydrogen
Cyclohexane Oxygen

Cyclohexanol
File:Test-plus.png
Cyclohexanone

Adipic acid HNO3

Shimmin 13:27, 25 November 2005 (UTC)

Hey, I really like this! I've always thought it was a shame we couldn't do links in schemes, now you've solved it! As you say, we need to agree on sizes & fonts. I have a system I like to use on ChemDraw for schemes, I will post it when I get home. I'd be interested in hearing K's comments too, he posts a lot of schemes. One question, does it tax the servers a lot to use this? Thanks for this great idea, Walkerma 02:54, 26 November 2005 (UTC)
There are no dynamic elements in this, so the wikicode only has be rendered once. On a per-page basis, this ought to be no more taxing than any other page that contains several images, and the images themselves are only a few kb each. Shimmin 13:10, 26 November 2005 (UTC)
I like it too!!! :-) -- this just opens a host of possibilities...we can be a small set of reusable symbols and use them in reactions and in the articles themselves! --HappyCamper 02:57, 26 November 2005 (UTC)
Shimmin, I must congratulate you on a most ingenious way of portraying schemes. I like it and I don't. What I really should say is that my first impression was one of horror, but over the years I've learned never to go with my first impression. You missed one HUGE positive for using these tables: with enough pieces, you can write schemes without having to use a chemical drawing program like ChemDraw or ISISDraw. That, in itself, is huge. One question I get asked the most often is: How can I draw schemes like that? It's always the same answer: Get yourself a program to do it for you. However, with this system, one could write a simple scheme without a chemical drawing program. I think if we could make chemical drawing programs a thing of the past, Wikipedia would be a much nicer place.
The alt text is another huge plus, because additional useful information could be embedded in a page.
However, there are a number of problems we should think about:
1) It will not save us any time writing schemes for pages. Although images will be reused, to describe some new reaction or scheme or whatnot, we will likely have to upload at least one new structure. If we have to upload two structures or more, then this system is already taking longer to use.
2) The wikicode is rather complex. I realize that the schemes will typically be simpler than the above table, but I would be hard pressed to make a table more complex than that. And, yes, to become a world-class chemistry reference, we will be making more difficult schemes than that. (Please see Nicolaou Taxol total synthesis for an excellent example.)
3) Standardizing everyone's images will be a living nightmare. It can be done, but it will take lots of work.
3b) V8rik uses alot of color in his images. I do not, but am trying to use more. Color usage would also have to be standardized, which may do more harm than good.
This system is well designed for describing simple chemistry, like stuff encountered in sophomore organic chemistry. This system is not well designed for the complex schemes like total syntheses or reaction mechanisms.
One problems to consider is also a practical one: to make this system become useful, ALOT of structures must be uploaded. Short arrows, long arrows, left arrows, right arrows, toluene with the methyl up, toluene with the methyl down, probably every compound in WPChemical's worklist, etc...
I propose that we use this system for a single page. Our own little experiment. Is it easy to code? Does it work within the Wikipedia? Does it look any better than the current page? Does it clarify any of the reactions? I propose Electrophilic aromatic substitution, because there will be lots of benzene image reuse, and the page need serious help. If it works for everyone, then we can discuss standardizing image specifications, and further steps needed.
~K 06:40, 26 November 2005 (UTC)
I completely agree with K's comments: let's do two or three trial runs to see how it works in practice. It would also be helpful if everyone could post the preferences (and the program) they are currently using for structures: we may well have problems of capatability between drawing programs...
I will be drawing some simple schemes for sodium amide this weekend, I will give it a go. Physchim62 (talk) 08:23, 26 November 2005 (UTC)

Here are my reflections on building the above example.

  • Breaking a scheme up into individual images was not really a pain. Once I had the scheme drawn in ChemDraw, I had to save each individual part of the scheme as a separate image file. This was only mildly tedious, and balanced by the fact that I did not have to spend time tweaking the positions of the pieces of the scheme to make everything line up nicely.
  • Resizing all these images would have been a pain, but I use IrfanView. IrfanView is free software that makes batch image manipulation relatively painless.
  • Individually uploading all these images to Wikipedia, and giving them redirects to the various compound pages, was a real pain. If I am going to do this on a regular basis, I will figure out how to automate it with wget.
  • Building the table was not a pain. For me, it was the easiest part of the process.

In conclusion, since any scheme of even moderate complexity will likely need a few "pieces" not already in the library, even when the library is well-developed, building complex schemes this way will always be more work than uploading them as a single image, and the question is whether that additional work is worth having links and alt-text for individual regions of the scheme. However, simple chemical equations (A + B -> C + D) will be very easy to embed once the library is well developed. Shimmin 12:53, 26 November 2005 (UTC)

For the record, the example images were made using default ChemDraw settings, except that TNR label text was done in Arial instead, then saved as PNG images and downsized to 33% of their original size with IrfanView. Shimmin 13:01, 26 November 2005 (UTC)
I don't have access to this software at the moment. Would something from Wikisophia be good? --HappyCamper 13:38, 26 November 2005 (UTC)
I meant to mention, if you don't have access to ChemDraw, you can go to www.mdli.com and download ISIS Draw for Windows for free. I wrote my PhD dissertation with an older version of it than this free version, and I still use Isis for most of my teaching, as I am more comfortable with it. For a typical example of an image drawn in Isis then scanned see this. You can see some discussion on Isis here and in the section following that. However we still need to spend a bit of time comparing formats and agreeing on standards. Though rather than creating our own settings, I wonder if we should standardise on one of the standard journal settings which are easily accessible in both Isis and ChemDraw. Walkerma 06:05, 3 December 2005 (UTC)

Should each scheme have a link to Structural formula to allow a lay reader to understand what the scheme means? CS Miller 16:08, 3 January 2006 (UTC)

BranchesofChemistry Template

Do people think that Green chemistry should be added to this? I think it probably should, as it isn't the same thing as Environmental chemistry, and there is a reasonable article for it. --Petros471 10:56, 20 December 2005 (UTC)

I'm just going to follow guidance Be bold and do it anyway, as no-one is immediately objecting. It can always be changed back... --Petros471 19:42, 21 December 2005 (UTC)

I added theoretical chemistry, which definitely should be listed. I was thinking about removing computational chemistry since it is considered (see chemistry and theoretical chemistry) as a sub-section of theoretical chemistry. If I don't here any complaints, I'll remove it.
By the way, I don't think Green chemistry should be listed, since it is not a true sub-section of chemistry, merely a way in which various chemical disciplines can be used for a certain purpose. Anyway I think this list could do with some trimming. But the question is how many subdisciplines do you want to show here? You could go a long way. The main chemistry article defines only a couple of main catagories...Analytical chemistry, Biochemistry, Inorganic chemistry,Organic chemistry, Physical chemistry, Theoretical chemistry. If you list these, you have all sub-fields incorporated.... Comments?--WijzeWillem 19:31, 12 February 2006 (UTC)

I think it's fine as is. ~K 19:36, 12 February 2006 (UTC)

Physical chemistry stub and featured article

I have recently added a physical chemistry stub template for articles which require it, will some will take a look at it?. Template:Physical-chemistry-stub; By the way, how featured article posted on Portal of Chemistry is decided? HappyApple 17:41, 25 December 2005 (UTC)

I'm not sure about the featured article...but I like the phys-chem stub. I think the new stub is very useful, although we probably need to dig around for more articles which should be tagged. --HappyCamper 17:45, 25 December 2005 (UTC)
So far, I have decided which featured article is posted on the Portal. The scheme is actually rather simple. I go alphabetically through the list of chemistry Featured Articles. Therefore, January's article will be titanium, and February's article will be alchemy. I hope this makes sense.
If you want we could come up with another mechanism, like posting Good articles or whatever you suggest. ~K 18:42, 25 December 2005 (UTC)
Finding articles to tag with the new stub tag is relatively easy: go through Category:Chemistry stubs (currently around 800 articles) and change the tags to something more specific. I will probably be doing this at the end of January, if no-one else gets there first! Physchim62 (talk) 17:04, 27 December 2005 (UTC)
Since it got favourable responses I just added the new template to the main project page, to encourage people to use it. Thanks for creating this, it's definitely needed. Walkerma 05:15, 31 December 2005 (UTC)
I think we need something for transition metals too... --HappyCamper 05:41, 31 December 2005 (UTC)
What do you mean exactly? Can the Inorganic-compound-stub not be used effectively? Walkerma 22:47, 2 January 2006 (UTC)
Ooops :-) forgot we had those! --HappyCamper 02:23, 3 January 2006 (UTC)

Wikisource MSDS

I have noticed a number of articles with links to WS pages that do not exist. Are these links that were broken with the WS lang switch or have they never existed? --BirgitteSB 21:34, 2 January 2006 (UTC)

These are from the old-style chembox, now obsolete. No one who used that infobox is still active in the project, but I suspect they planned to have separate MSDS pages here on Wikipedia, something we now consider to be a waste of our time. I don't know of any that were ever written. The new chembox links to a data page which (if written, many aren't yet) includes a list of external links to commercial MSDS sheets. If you can let us know the pages that you found, we can make sure we update their chemboxes to eliminate the problem. Walkerma 22:44, 2 January 2006 (UTC)
Here are the one I found doing a search for "WikiSource MSDS"
These have now all been fixed. Physchim62 (talk) 14:23, 20 January 2006 (UTC)

Just out curiosity does the chembox you use now list the CFR49 acceptable name? I have always had difficulty find aplace to cross-reference the name required by OSHA against the DOT name for shipping. --Birgitte§β ʈ Talk 02:24, 3 January 2006 (UTC)

To answer your question, no, we don't as yet list any approved names (apart from INNs for drugs). I agree that this would be useful (although certain other editors are slightly worried about possible legal implications). If this gets off the ground, it would be tucked away on the data page for each compound, in a Regulatory information section: such a section could also include other info which doesn't usually appear in the chemboxes for lack of space: PELs, TVAs etc etc and their equivalents in other English speaking countries. Remember as well that Wikipedia uses Aluminium as its preferred spelling, while the US DoT insists on aluminum... Physchim62 (talk) 14:57, 6 January 2006 (UTC)
I understand the difficulties with that. Perhaps in the future we will have the CFR 49 on Wikisource (or at least the relevant tables) and you will be able to link to such information.--Birgitte§β ʈ Talk 15:14, 6 January 2006 (UTC)
29 CFR 1910.1000 seems like more of a priority to me (it's actually on my to-do list). However, an article on transportation regulations in the US would be very welcome on 'pedia (I'm a Brit based in France, so I have no day-to-day experience of the subject). Physchim62 (talk) 15:24, 6 January 2006 (UTC)
Be happy about that; USDOT doesn't seem to mind having thier own system completely uncomforming with anything else, even other US regulating bodies. They finally switched POISON to TOXIC which took too long since we share a border with a French speaking region. But I think it would be great to have 49 CFR 172.101 and some the appendices on Wikisource because of the ability to link back to actual chemical names and categories because CFR 49 uses alot of indiscriminate names. When you get your project up and going please send me note because I would like to see how you set up the table as I have no idea how to even begin something like that.--Birgitte§β ʈ Talk 20:18, 6 January 2006 (UTC)

List of publications in chemistry

I have taken an initiative on this page, which I think has some problems and needs opinions from a wider group of chemists. Please see what I have written on Talk:List of publications in chemistry. Bduke 23:08, 2 January 2006 (UTC)

Wikipedia talk:Stable versions#Certification gang

would you like to create certified articles in chemistry? -- Zondor 03:21, 5 January 2006 (UTC)

Group 3

This is spawned by an innocent edit of uranium and by the discussion that followed at User talk:Nrcprm2026#Group numbers. Since its early beginning, Wikipedia:WikiProject Elements uses (and mostly kept) the systematic data from http://www.webelements.com/ for its "Group, Period, Block" entries in the infoboxes of the chemical element articles.

WebElements.com omits the group numbers for the lanthanides and actinides. It is supported by the ungrouped elements page. On the other hand, that article gives no reference and might be a self-running soap bubble based on the circular reasoning that we never included group numbers.

It seems just as reasonable to assume lanthanides and actinides altogether are an inset of group 3 (and thus part thereof), below scandium and yttrium. There's the occasional edit to the infoboxes in this regard. What bugs me, trifle that it is, this basic definition affects the consistency of quite a number of articles.

The definition at periodic table group as a "vertical column in the periodic table" is not at all clear, and the discussion at talk:periodic table about whether or not Lu and Lr are placed into group 3 would not make sense if they'd be group 3 in any case. The group 3 element article puts them all in group 3 but other than that is no help either and it lost me at "All of these elements are classed in Group 3 because their outer electron shells hold three electrons."

So, the question is what the heck is group 3 anyway? Is this a matter of convention without clear definition (like what's part of the lanthanides), and one might find references either way if one digs deep enough? None of the above comes close to being a definite, authoritative reference. Could a real chemist set this straight please? Femto 18:09, 13 January 2006 (UTC)

I, too, would very much like to know whether some or all of the f-block elements are considered part of group 3, and if so, which. I have promised to check the IUPAC Red Book soon, but that may take a week. --James S. 22:28, 13 January 2006 (UTC)
I've checked the Red Book (IR-3.6) for you, and it doesn't seem to give much help. The current definitions are inconsistent, as they admit themselves, as to whether the lanthanoids start at lanthanum or cerium: this is the result of a compromise, as can be seen in the definition of transition element. IUPAC never went near the question as to how they numbered the "groups" in the f-block, although they did institute a new numbering for the other groups which has now been largely accepted. My advice would be that elements between cerium and ytterbium and between thorium and nobelium have no accepted group number. The situation is more difficult for lanthanium, lutetium, actinium and lawrencium, but the current Wikipedia practice of placing La and Ac in group 3 is widely followed in published periodic tables. Hope this helps! Physchim62 (talk) 16:55, 14 January 2006 (UTC)
Very much. So they can tackle the spelling of aluminium, but they chicken out on the basic definitions? :) See further Wikipedia talk:WikiProject Elements#Group number convention. Hope I got it all right. Femto 19:52, 14 January 2006 (UTC)
I note that Group 3 element currently lists lanthanides and actinides as members, should this be updated? Or should we just say "some authorities also include the following as members of group 3, but IUPAC has not yet made an official ruling." Walkerma 15:29, 17 January 2006 (UTC)
For the time being, it should suffice to make the page more neutral and less definite. The exact nature of the example becomes secondary then. (The latest addition has only muddled it further I'm afraid. First there's "elements in group 3 (IUPAC style):", then "it seems that IUPAC does not include the Lanthanides and the Actinides in group 3". That's not neutral, that's confusing.) See also the talk that followed at WikiProjectElements about my opinions on the need for more coordination of these pages and the strict separation between neutral descriptions and defining coherent examples. Femto 17:18, 17 January 2006 (UTC)
If I might might venture my opinion, IUPAC haven't bothered to give a precise definition here because there isn't a precise and useful definition to be had! The concept of verticle groups, whilst provided a marvellous way to label several elements together and compare trends in the properties in *some* cases (eg alkali metals, noble gases, halogens...), isn't that much use for the f-block. Already in the d-block, horizontal trends begin to be important, and by the f-block, horizontal trends are key. People doing comparative chemistry on actinides and lanthanides look horizontal, not in vertical groups. There are certainly very few useful vertical comparisons to be made between the bulk of the actinide sequence, and scadium and yttrium. Defining a 'Group 3' largely makes most sense in terms of electronic configuration, in which case you can make the best case for Group 3 being a d-block group of Sc, Y, Lu, Lr, and have the lanthanides and actinides as f-block footnotes. You can also compare this scheme to a Group 3 of Sc, Y, Ln, Ac - although Ln and Ac do have more behaviour involving partially-filled f-orbitals, so this is second best. --feline1 16:59, 19 January 2006 (UTC)
Wikipedia should not follow http://www.webelements.com in terms of the layout of the table because the webelements table is misleading. IUPAC is definite about Lu being a lanthanoid and Lr an actinoid (see the second to last page here: http://goldbook.iupac.org/reports/provisional/abstract04/RB-prs310804/Chap3-3.04.html). The webelements administrator wrote last summer: "We could certainly argue that my WebElements home page (and a lot of books) is a bit loose in that I have labelled the first row of the f-block as lanthanoid without making it clear that Lu is one as well. I'll find a way to clarify that..." but they haven't done so yet. See the lengthy (and sometimes very silly) discussion here: http://forums.webelements.info/viewtopic.php?t=2334&postdays=0&postorder=asc&start=0. I think an encyclopedia should represent conventions the best way it can without making stuff up, so I was surprised by the ungrouped elements article, since I've never heard this term before. Flying Jazz 00:57, 21 January 2006 (UTC)

Please check out the changes at the group 3 element article and the replacement of the "ungrouped elements" article with the group number of lanthanides and actinides article. Nobody is an "authority figure" about this kind of stuff because it's a little arbitrary and a matter of opinion, but that's OK and kind of cool too. Flying Jazz 16:16, 21 January 2006 (UTC)

Analytical chemistry stub template

I have just made an Analytical chemistry stub template, i belive there are many articles should require it, what does wikichemists and community thinks about it?.HappyApple 22:22, 14 January 2006 (UTC)

Looks good. ~K 22:32, 14 January 2006 (UTC)
Yep, nice. Put it on the Wikiproject page, and start using it. Wim van Dorst 23:26, 14 January 2006 (UTC).
Ditto. Great. Use it. Bduke 23:30, 14 January 2006 (UTC)

Identification

Can anyone tell me what compound this is?

File:OrganicChemistry.gif

Thanks 68.63.88.28 03:40, 16 January 2006 (UTC)

It's a disaccharide of some kind, i.e. something related to sucrose (sugar). However several of the OH groups seem to be axial (if I'm seeing it right), which rules out any of the common disaccharides since these all contain at least one glucose component. Walkerma 04:45, 16 January 2006 (UTC)
The one to the right is glucose (α-D-glucopyranose). The one to the left is a furanose, but I haven't identified it yet (unclear image). --Eddi (Talk) 02:00, 21 January 2006 (UTC)

Equilibrium arrows

There are a lot of articles in Wikipedia, where authors insert a math equation and use the equivalent of a resonance arrow for an equilibrium arrow. Is there anyway in the math equation to use a more proper arrow? Should pictures be inserted instead?

Try \overrightarrow{\leftarrow}, e.g:
<math>Na^+ + Cl^- \overrightarrow{\leftarrow} NaCl</math> produces
I would rather use "harpoons" than arrows, but after experimenting with math formats for half an hour, I doubt they are workable. --James S. 18:51, 24 January 2006 (UTC)

Actually there are little-known Unicode symbols for equilibrium arrows ⇌ (&#8652;) and ⇋ (&#8651;). I would recommend the 8652 one for most things. I retrieved these from the archive. These symbols work with normal text in our standard equations, see ammonium thioglycolate for an example. Personally I think the Math font looks ugly! Walkerma 21:37, 24 January 2006 (UTC)

Uh-oh, walkerma, I just switched ammonium thioglycolate to the ugly kind, as you call them. Using the 8652, I only see ? on my Camino browser, which is able to decode the math method described by James S. Smokefoot

Sulfuric acid manufacture

There is an article about it, Contact process, and there is an incomprehensible summary at Sulfuric_acid#Manufacture. I suggest that the summary be deleted or the articles merged. --Dfeuer 01:46, 25 January 2006 (UTC)

Would the best solution be to delete Sulfuric_acid#Manufacture or rather replace the whole of that section with the full content of Contact process and then redirect Contact process to go to Sulfuric_acid? I suggest we wait a week to see if people object to this or prefer another option. --Bduke 01:59, 25 January 2006 (UTC)
  • Go ahead, be bold, and do the improvement. That's what wiki is about. Wim van Dorst 21:45, 25 January 2006 (UTC).
This is a standard problem we find in all commodity chemicals. I would suggest the following guidelines:
    • If the process is a very important one, it deserves a separate page to give full details of the process.
    • The product(s) made by that process should have a brief outline of the process in the product page, under #Manufacture.
Some examples:
If our encyclopedia is to be complete, we need both descriptions for all major processes and all major products. Those major products all need a short description of their manufacture. I would argue that as the worlds's no.1 commodity chemical, the sulfuric acid article needs a summary of the Contact process. As the world's largest volume process, the Contact process needs a thorough article on it. If we merge or delete, then we need to do the same to acetic acid, sodium carbonate, ammonia, sodium hydroxide, and so on. Do you think acetic acid would have become an FA without a description of how it is made? Shouldn't sulfuric acid be written to the same standard?
The summary at Sulfuric_acid#Manufacture is described as "incomprehensible." It seems to me to be a very straightforward description of the process. However if you find it incomprehensible, then please rewrite it so that it becomes comprehensible, while keeping it very concise. Don't just delete it, that makes it even less comprehensible! Meanwhile I think the Contact process article needs expanding so as to give the necessary level of detail, it's only at "start" level right now. It needs to include a section on the energy efficiency aspect (the economics of the process are totally dependent on recovering the "waste" energy from the exotherm). It should discuss the main alternative ways of reacting the SO3, you can either react it with 97% H2SO4 to make 99%, or you can make oleum then dilute that with water. It should discuss different catalysts, history/technological developments, etc. Enough for a 10 page article, I'd say! Walkerma 22:54, 25 January 2006 (UTC)

I bow to your greater knowledge. I was certainly not going to be bold as instructed and do what I suggested. As I said I was waiting a week for others to comment. I think we have the comments. You are right. --Bduke 23:00, 25 January 2006 (UTC)

I agree with Martin, Wikipedia is NOT a paper encyclopedia, there is room for both the summary and the main article. These sections are actually quite difficult to write, so all help and/or comments are welcome! Physchim62 (talk) 08:54, 26 January 2006 (UTC)

Rhodium(III) chloride, iridium(III) chloride

Minor rant 1: no one who works with rhodium or iridium uses the terms we have for article titles : Rhodium(III) chloride. In the lab and in the classroom we say "rhodium trichloride". the same applies for other tm halides. Minor rant 2: the article on rhodium(III) chloride, at least before I worked on it, perpetuates the misconception that hydrates and anhydrous metal halide are simply differ by nuance or some sort of chemically insignificant inconvenience. Hydrates and anhydrous compounds are different chemicals, period. Thus, the Rhodium(III) chloride article was tricky because the previous draft stated that "RhCl3" is useful in coordination chemistry, whereas coordination and organomettallic chemists of course only use the hydrate. The anhydrous stuff is useless. I propose that the Rhodium(III) chloride article be relabeled "Rhodium trichloride", because that is the stuff practioners use. I dont know how to relabel an entire article yet.Smokefoot 22:24, 29 January 2006 (UTC)

We have typically used the Stock name of type "Metal(III) halide" for compounds like this, that's why the page was named that way. I did a quick Google search: "Rhodium(III) chloride" (in quotes) got 1710 hits and "Rhodium trichloride" got only 500. Even if we allow for the fact that some of the 1710 are complexes, I don't think it's fair to say that rhodium(III) chloride is an "unconventional name" for the compound. On the English Wikipedia we have people from Australia, England, Canada, the US, the Netherlands, and many other places, and so it is often hard to say that a certain name is never used - different countries often have different traditions, like aluminum vs aluminium. Here in the US, as far as I know all chemical catalogues (except sometimes GFS) typically use the Stock name, even in silly cases like PCl3! There is also the spoken vs the written word; in our lab we always speak about our Dy(OTf)3 catalyst as "dysprosium triflate" yet in many published articles it is referred to as "dysprosium(III) trifluoromethanesulfonate." The Stock notation is ugly when spoken, but very clear when written. Likewise no one I know would refer to n-propanol as propan-1-ol in the lab!
Be aware also that the article name isn't so critical. If you click on a link to rhodium trichloride you'll see there is a redirect to the rhodium(III) chloride page. If you click on the rhodium trichloride link at the top of that page, you can take a look at how redirects are done.
That all said, I can accept that rhodium trichloride is the usual name used outside the catalogues. Of course "those who work with Rh/Ir" aren't the only judges here - we need a name clear to all users - but here both names are fine IMHO. I would like to get PC's opinion on this - he has publications using Rh and Ir complexes, and he is usually no fan of the Stock name. If he's OK with it, we'll change the names over, I don't have strong feelings, as long as the redirects are in place.
One thing I'm concerned about, though, is deleting or commenting out parts of the content, if that content is valid and could be considered reasonable - especially in a case like this article, where it needs more content! If you're simply holding the text in a comment while you move it around, that's fine. For any article on a metal halide, I consider the most important complexes to be the hydrates and those of the halide. I had put in a section about the chloride complexes and their redox chemistry, taken from Greenwood & Earnshaw; there is now no mention of oxidation to Rh(IV) or even of the chloride complexes. In addition, I see that the organic section has also been removed as "esoteric." It may be esoteric to an inorganic chemist, but after the Wilkinson catalyst section it is the most interesting thing to an organic chemist such as myself (and to Swan & Black, who saw fit to describe these reactions in detail in their very concise book). In summary, it is considered "bad form" to remove serious content without discussing it first. If information is wrong and unsupported by references it's another matter. If it is valid and backed up by relevant references (as all of this was), then you need to have a very good reason to remove it, usually backed up with evidence. I had spent several hours researching material to help bring the article to A-class, I do not want to see it removed without discussion.
Wikipedia depends on a variety of editors to provide a variety of viewpoints on a topic. I really appreciate the input from an inorganic chemist who has the familiarity with the complexes prepared from RhCl3, I think this has really enhanced the article. Clarifying the differences between the anhydrous and hydrate is also important. However I don't like to see my input (the "organic chemist's view") removed. If this is just temporary while you reorganise the article, that's fine. If there is a sentence I wrote you really object to, let's discuss it and fix it. As an organic chemist writing about an inorganic compound, I realise my knowledge of crystal field theory is very hazy and I may get things wrong from time to time, but the alternative viewpoint I bring is (I think) valuable to the article. Walkerma 05:03, 30 January 2006 (UTC)

Walkerma: Sorry about the putting things in comments. I am going to revert them back after I can figure this article out more. I just want to look up some things. The dimerization of ethylene and the O2-Rh-py thing is interesting. And Rh(IV) too. The organic applications are huge obviously. Apologies if I went overboard, its just that even hopping between the sandbox and the preview I can only get so far and I ran out of time. Comments and perspectives on who looks for what in terms of rhodium chloride are welcome. Actually, I am not absolutely, absolutely sure that anhydrous RhCl3 is useless, but I have heard horror stories of students who order 100g of this stuff and it does nothing. The monographs are a little vague. Also on the exact speciation of RhCl3 in water. I will insert these same comments on the rhodium(III) chloride discussion page.Smokefoot 16:20, 30 January 2006 (UTC)

That's fine then, I was just worried you were going to remove it all! That's why I do major edits offline in MS Word. I also uncovered this earlier discussion on RhCl3, including my embarrassing blunders (yes, I know I over-use the 18 e- rule also!), PC is very familiar with this compound too so he can probably provide refs and insights. I'm pretty sure you're right, even I know that Rh(III) is kinetically inert (I wrote the CrCl3 page, and that is similar). As for students who order 100g, I'd like to meet the PI who's let their student order over $10,000 worth of stuff in error! Walkerma 17:34, 30 January 2006 (UTC)
A guy in the last research group I was used some anhydrous RhCl3 to prepare bi-metallic nanoclusters. I never heard if he got any results, though. He certainly didn't order more than 1g. -- Rune Welsh | ταλκ 20:22, 30 January 2006 (UTC)

Just supporting Martin here: removal of content on a substantial page (Chem A-Class isn't just any page) warrant some good discussion first, e.g., in the talk page of WP:Chem (Chemicals, not Chemistry). Wim van Dorst 21:30, 30 January 2006 (UTC).

Okay: about removing content, or hiding it in temporary comment. I am going to uncomment that stuff soon. Help me with this factoid(?) that I hid from sight temporarily: "Oxidation of aqueous ethanolic solution of pyridine (py) and RhCl3 by air affords blue paramagnetic [Cl(py)4Rh-O2Rh(py)4Cl]5+." Just because I've never seen this thing, doesnt mean that it's not worth mentioning in a thumbnail sketch of RhCl chem. So I looked it up on SciFinder, one hit (Dalton Trans 1973 by Gillard) speculating based on polarography on this molecule. Then I looked at the most recent Rh-O2 paper: Rhodium-Mediated Formation of Peroxides from Dioxygen: Isolation of Hydroperoxo, Silylperoxo, and Methylperoxo Intermediates** Angew. Chem. Int. Ed. 2005, 44, 6947 –6951. Not mentioned. I will keep looking. BTW, I would welcome any references to Rh(III)-Cl-H2O things in soln.Smokefoot 23:27, 30 January 2006 (UTC)

Photochemistry

Hi, everyone. I'm starting to spearhead the development of the Photochemistry article. And from stuff that I am thinking about covering, it is going to be huge :S (might have to split off into other articles too! :D) So far, I've been copying stuff from wikipedia -- light, optics, specialized articles into the photochemistry article. Everyone is welcome to pitch in or let me know how I'm doing, or give me suggestions. I am a busy university student so this will be a slow work in progress. Most of the information at the top is a place holder until the main article is done. Jawz 06:50, 31 January 2006 (UTC)

Wikipedia talk at ACS Atlanta

For those of you who may be attending the American Chemical Society national meeting in Atlanta, I would like to encourage you to attend my talk, "Wikipedia: Social revolution or information disaster?" It takes place at 10:35 am on Sunday, 26th March, as part of the Chemical Information Division's session on "Social Software." I'd appreciate any thoughts & suggestions you may have. I plan to present an NPOV (of course!), showing the pros and cons of Wikipedia, focussing on its use and value as a chemistry resource. Many of the attendees for the talk are likely to be science librarians, though there will be many chemists too. Come and ask some thought-provoking questions! Walkerma 22:55, 10 January 2006 (UTC)

I won't be able to get to the meeting. (I'm very jealous of you.) Could you post your slides somewhere either before or after the meeting, so we can have a peek? ~K 03:27, 11 January 2006 (UTC)
Please show off my recently un-stubified Chemist article. --James S. 22:25, 13 January 2006 (UTC)
(Now with added Erlenmeyer flasks!) --James S. 02:15, 18 January 2006 (UTC)

Talk:Cyclohexanone illustrates one of the problems which any chemical information resource has to cope with! Talk:Cyanide has had a recent debate illustrating the difficulties of using even web-available, peer-reviewed sources; Folic acid is almost entirely based around a single (US Federal Govt) source. Will that do you for ideas for this weekend? ;) Physchim62 (talk) 16:36, 14 January 2006 (UTC)

Thank you for all the suggestions! There are of course so many things to talk about. Thanks also for the major expansion of the chemist article; we will need to make sure that it is distinct from the chemistry article. Are any of you going to be there to heckle, or maybe to meet up with me? Cheers, Walkerma 17:19, 18 January 2006 (UTC)

Project template

This user is a participant in WikiProject Chemistry.

is is userbox that is a specific use of Template:Participant. It shows a link to "participant" that calls [[Category:Participants in WikiProject Chemistry]]. This category does not exist. Do we want it to? If so how do we do it? Or do we want a different userbox that indicates participation in this project? Bduke 10:17, 19 January 2006 (UTC)

I just clicked on the redlink and saved the category with a link back to the project article. Anyone can add {{participant|Chemistry}} to their userpage. --James S. 18:12, 24 January 2006 (UTC)
Checking recently, I see that [[Category:Participants in WikiProject Chemistry]] has nobody in it, except this talk page and I have just fixed that by "nowiking" the Cat above. On reflection I do not think we want that category and I have seen some move against categories for Wikipedians. I suggest we have a userbox like the one above but without the Category being added by the template automatically. --Bduke 06:01, 7 February 2006 (UTC)
No, I did not fix it. Displaying the box of course adds this page to the category. --Bduke 06:03, 7 February 2006 (UTC)

Electrochemistry article

I have been tireless working in Electrochemistry article, for over a couple of weeks. I have added substancial information regarding the history of electrochemistry and a summary of what is involved, most of the article has reference in Brown LeMay Bursten General Chemistry book and Chang Raymond too, thus i attempted to do an introductory article showing a general view of the whole aspects (or most of them) studied on electrochemistry. I would like to know what do other wikichemists think about it?.HappyApple 07:45, 30 January 2006 (UTC)

Very nice. A little style stuff and grammar here and there, but I like it. I really do. Jawz 08:36, 30 January 2006 (UTC)
That's great! I for one really appreciate all the work that went into it. It's also one of the "proposed goals" articles for WP:Chemistry. Thanks a lot! Walkerma 05:50, 1 February 2006 (UTC)

3D models of molecules

Ferrocene
Ferrocene
Biotin
Biotin

Hi, I have started to create 3D-models of about 200 molecules, which I could upload to Wikipedia. As an example of what could be done with it, see the infobox at Caffeine. I have no experience editing articles on chemistry, so your thoughts are welcome. Is this a good idea? Mstroeck 23:56, 30 January 2006 (UTC)

  • Space filled models I think are a great addition to the line-drawn molecules! Kudos! (Can we make the background all one color?) Jawz 02:16, 31 January 2006 (UTC)
    • I've done a few tests so far, but haven't really created many pictures, so yes, we can change anything we want :-) I'd also like to have some feedback on the colors for the atoms. I posted a request for feedback over at the WikiProject Chemicals talk page, where somebody remarked that, for example, carbon atoms should be black. The software I use automatically colors them green, but it's no problem to recolor them. I'd like to have some feedback from people who are actually chemists, which I'm not. And yes, we can have the background in one color. I've noticed myself that having a gradient is actually not very appealing. BTW, eventually, I'm going to animate these atoms, so we'll have spinning 3D-represantations. If anybody could point me to Mac OS X software that creates animated GIFs out of AVI files, I'd really appreciate it. Alternatively, I'll be happy with a simple animated gif tool, as well. Mstroeck 03:14, 31 January 2006 (UTC)
      • It escapes me at the moment (maybe someone can alert my attention), but I can't remember if there is or is not a international standard on molecular modeling regarding atom color. If there isn't, it probably would be a good idea to have a discussion about what we want to color everything :) Jawz 03:47, 31 January 2006 (UTC)
        • While I'm wating for more feedback, I have created some new models according to suggestions, have a look at caffeine again and tell me what you think. Mstroeck 16:25, 31 January 2006 (UTC)
          • Caffeine looks nice. And thank you for following the color convention. Some suggestions from an inorganic enthusiast: Flat molecules, or "flattish" molecules need drawings less than 3-d things. Ferrocene could use help. And as other suggested, both space filling and regular would be nice. Molybdenum hexacarbonyl is another. Butyl lithium is shown as 1-lithiobutane, vs the cubane structure. The structure of Cu2(OAc)4 is nonintuitive and common to several metal diacetates. Others might include various metal clusters. Smokefoot 02:05, 1 February 2006 (UTC)
          • Beautiful :) Jawz 02:28, 1 February 2006 (UTC)
            • See images. Feel free to add them to their articles, if you think they are correct and look good. Mstroeck 03:42, 1 February 2006 (UTC)
Nice job! BTW, Smokefoot, did you mean Chromium(II) acetate? (Good choice IMHO) Walkerma 04:50, 1 February 2006 (UTC) Well, as far as I recall, Cu(II), Cr(II), Mo(II), Rh(II), Ru(II.5 and II) acetates look fairly similar (Chinese lantern structure is how we describe them), varying mainly in their M--M distances and axial ligation. But maybe I need to recheck. I am hoping to get convince a student to write up "quadruple bonding", and they'll deal with this. But regardless, the pics of FeCp2 (to the right on my browser) are lovely indeed and Mstroeck has made a "master stroke" (IMHO, also). Hopefully someone can insert this art. Smokefoot 05:05, 1 February 2006 (UTC)
I've learned the ways of Mstroeck! I don't have as much experience as him (his images of the eight allotropes of carbon are beautiful) but I'll be happy to make 3D models of any compounds you guys want doing. I've started on some amino acids.
Ben

Idiot at work?

For some reason this person keeps revising the oxidizing agent site. This is a minor site, but I am trying to figure out what this dude is trying to get at, check out the following things that keep creeping into this article: “An oxidizing agent is a acid that oxidizes another substance” an ACID? “This reduction process means that the other substance forms an ionic bond between the two molecules” And what is this state supposed to mean, I see words but no meaning. Am I being hypersensitive? Smokefoot 01:21, 31 January 2006 (UTC)

  • I wonder if this is the same dude from my chemistry class. Last week he and the professor had a heated debate, during lecture time, about acids and bases being reducing or oxidizing agents. In short: Yes, they do "some" (yes, quotes...) form of oxidation/reduction based on the transfer of protons and electrons BUT THEY ARE NOT oxidizing or reducing agents! The transfer of protons and electrons can very easily be reversed. In classical redox reactions, some electrical potential difference/energy must be input to drive the reaction backwards. I hope this helps. Jawz 02:14, 31 January 2006 (UTC)
Thankfully in chemistry we have less controversy to worry about than (say) in politics, although we did have someone trying to claim that Aldol reaction had a POV problem recently! However we do get schoolkids who have taken a chem class or two and think they know it all: "A little knowledge is a dangerous thing." Thankfully we have enough PhD chemists around here that we can usually deal with the problems, usually with a dozen refs to back it up! And let's remember too, we all get things wrong. One of my favourites from when I joined Wikipedia is here. Welcome to Wikipedia...! Walkerma 17:34, 31 January 2006 (UTC)
POV on Aldols rxn? That must've been interesting. Yes, I will remember that everyone makes mistakes -- You will probably get to talk to me again once and a great while. I have gotten a few things wrong recently in my endeavour to try and help the wikiproject. Thanks for your words Jawz 02:31, 1 February 2006 (UTC)
I was doing a little research through my analytical textbook the other night, and came across something (no more than a few sentences) that discusses this. If you want the reference I can provide it; it said something to the effect that acids/bases can participate in redox, but it is not a true redox it is a "conjugate redox" -- and that vocabulary isn't used. Very much. at all. So, maybe that makes more sense for those who were slightly confused? (like me? :) ) Jawz 02:36, 2 February 2006 (UTC)

Well nitric acid is definitely an oxidising agent, and hypophosphorous acid is a reducing agent... Many substances are stronger oxidising agents in acidic solution, due to the Nernst equation, but this is not really the point. Redox reactions are about electron transfer, acid-base reactions are (to a fairly good approximation) about proton transfer. Physchim62 (talk) 23:40, 2 February 2006 (UTC)


Transition metals

I tried some clean-up on this (clearly important) article, but it needs help. Any takers? Olin

Can I also ask for help? Olin has made many significant revisions. There are two main changes:
  1. Taking a side on the question of what transition metal means, preferring the functional to the traditional definition.
  2. Replacing scandium with cadmium as the second debatable member of the transition metals (the first being zinc).
These may well be correct, I'm just flabbergasted that the second in particular wasn't picked up before if so! Andrewa 08:49, 3 February 2006 (UTC)

I hope I didn't cause a ruckus here, but scandium didn't make sense according to the IUPAC definition, and I did look around a little in some books--I will look some more today. Olin

(Later) I looked in Cotton & Wilkinson--a classic advanced inorganic book for graduate school; it clarifies the situation. I'll make the changes later today or this weekend, and cite them. Olin

OK--it's fixed. It turns out mercury is excluded, too. I trust the reference--it's used a lot in graduate inorganic courses and it has separate chapters on transition metals and group 12. Thanks for all of your patience. Olin


Well I am not sure that splitting hairs about what is an official TM or not is the tone we should send, we are a chemists, not lawyers IMHO. I looked at the site, it's quite nice and concise - those that worked on this should be congratulated. The oxidation state graph could be expanded if we want to mention zero- and negative oxidation state (Fe(CO)4]2- etc), I think that the block-buster Tc drug is Tc(I). I also added the following comments to the section: "There are several common characteristic properties of transition elements:

  • They often form coloured compounds" I inserted "often" to acknowledge most M(CO)x's, most d6 hexacyanides, most Ag+, Pt(II) species.

"*They can have a variety of different oxidation states" -OK (but so can most elements? -see comment below about redox (esp 1e redox).

  • They are often good catalysts This phrase propagates the concept that catalysis is generic - virtually every known compound catalyzes some process. Protons are great catalysts - okay, I haven't figured out what pentane catalyzes yet, but you get my drift.

"*They are silvery-blue at room temperature (except copper and gold)" OK

  • They are solids at room temperature (except mercury)" OK

"*They form complexes, which is described by crystal field theory." Why say the latter sub-phrase? CFT is NOT a "characteristic property" of the TM's, it's a characteristic of how humans describe the electronic properties of TM complexes? Anyway, CFT is a nice starting point, but MO-LFT is probably more useful since it actually acknowledges bonds, vs. electrostatics. Other characteristics - TMs are virtually unique in undergoing easy (low potential) redox, and TMs are often magnetic (as are many lanthanides...).

Also given the interest in bio-inorganic, it would be neat to mention which are "essential" for life. Maybe another site discusses essential elements?Smokefoot 15:01, 3 February 2006 (UTC)

I'm not going to get takers for this outrageous idea, but can we define transition metal as a metallic element in the middle of the periodic table? The subtle differences in chemistry between the elements is what makes (IMHO) their study so interesting; we can describe the dispute on nomenclature without taking a normative stance. Physchim62 (talk) 20:40, 3 February 2006 (UTC)
See the talk above. Again, I do think there is a real definition, so I think making one up is a bad, bad idea. Olin
There are plenty of definitions, the problem is choosing which one to choose! Cotton & Wilkinson who say that mercury is not a transition metal, Greenwood & Earnshaw who say that zinc is a transition metal or the people at IUPAC who have never had to write a textbook? Physchim62 (talk) 21:08, 3 February 2006 (UTC)
This seems to me to be one of those wonderful opportunities for those in the physical sciences to really grapple with NPOV. There are several definitions, some more authoritative than others, none with consensus support. In a democracy, we'd simply ignore the minority views, thus attaining peace and justice (;-> but here, we aim for consensus and NPOV... whatever these might be. Andrewa 08:45, 4 February 2006 (UTC)
In defense of the current page and to clarify a bit what Physchim62's wrote above, Cotton and Wilkinson is consistent with the IUPAC definition--Zn, Cd and Hg all are d10 and do not make ions that have part-filled d subshells. And Greenwood and Earnshaw would be consistent with the first definition in the article. These two definitions are the only two. What makes the transition metals interesting is their properties BECAUSE OF the part filled subshells, and I think that's why there's the group 3-11 vs 3-12 conflict. Group 3-12 is "easy" visually since it is the d-blcok, but 3-11 is more consistent with interesting properties due to unfilled shells. I had screwed up in my last definition not discluding mercury because I was confused about mercury(I). But since it is Hg22+, it doesn't really count for an unfilled shell (my bad!). So the two defintions are really only two. Olin
Not to cause trouble, but I guess that lanthanum is not a lanthanide? Its chemistry does not involve partially filled f shell. Even Greenwood and Earnshaw struggle with this point. Despite my dislike of nomenclature discussions, it is worth hashing this out.Smokefoot 21:59, 4 February 2006 (UTC)
A web search does show that lanthanum is not always considered a lanthanide. Oh, bizzare. I'm not changing anything until I find a citeable source. Olin

Heterocycle/Heterocyclic compound

Can these two articles be merged, with a redirect from heterocycle to heterocyclic compound? I put a merge notice at the top of both. Olin

I have edited the merge tags to the specific mergeto and mergefrom tags to clarify what you want. This alters the article for discussion to Talk:heterocyclic compound, as it should be as the final main article, and it is actually where the discussion had actually started. It would be very obvious and easy to do. I suggest you just do it. I only noticed this when coming to write the section below. --Bduke 07:30, 6 February 2006 (UTC)

Check Lanthanide contraction article

Can someone check Lanthanide contraction? It needs expert attention. Wendell 03:08, 12 February 2006 (UTC)

All the stuff in the article are the consequenzes of the Lanthanide contraction not the Lanthanide contraction. I always thougt the Lanthanide contraction is that the Lanthanides decrease their ion radii while more and more electrons are added in the periodic table. This happens due to the fact that the electrons are added to a relative low shell and the increasing number of protons atract the new electrons. The effect is the Ion gets smaller with increasing core charge. The results of this are the things mentioned in the article.Stone 10:31, 13 February 2006 (UTC)
I tried to do something but the increase and decrease words I use to often. So somebody should have a look. The chemistry should be clear, but the language is my problem.Stone 09:06, 24 February 2006 (UTC)

Caesium Lithium Borate

What should we do about CsLiB6O10? --HappyCamper 02:09, 13 February 2006 (UTC)

The article contains no links and the very very very technical language makes it only useful for specialists. Non linear optics is very interesting but someone with knowledge should read this and add some links. Sorry, physical chemistry was never my favorite so I know only the basics.Stone 10:14, 13 February 2006 (UTC)

Phosphorous acid and phosphite

Would some expert look at phosphorous acid and phosphite and pass on advice here. The acid site is semi-lame, but want to hear advice before working on it. Probably chemical wikidedians have already debated and resolved the need for articles on the acids and their conjugate bases. On some talk page I saw a comment suggesting that we have an article on oxyanions, which would be one way to address the problem with HPO32- etcSmokefoot 18:31, 13 February 2006 (UTC)

Systematic names

Don't you think the article titles of some compounds should their systematic names according to the IUPAC regulations? For example, the 'formic acid' article should be titled 'methanoic acid', because that is its proper name. That's how they teach it in schools, and it is these names that are more internationally recognised.

Obviously it wouldn't be practical to title the 'insulin' article with its IUPAC systematic name, but where feasible, I think it should be done. snellios

Actually, I would only agree if there are links from the common names. Remember the audience for Wikipedia is the general public, who is much more likely to have heard of acetic acid rather than ethanoic acid. Olin 13:37, 16 February 2006 (UTC)
I would advocate that we choose the name which would be most educational for the reader. --HappyCamper 13:42, 16 February 2006 (UTC)
Yes, but I think it's more educational to point out that formic acid is the IUPAC preferred name for this compound :) Physchim62 (talk) 13:53, 16 February 2006 (UTC)
I have to agree with PC. If children are learning names like methanoic acid in schools, it's our job to try to teach them the correct names (see the IUPAC rules). Reinforcing this, when a particular name predominates in common usage, we prefer to use that name. A Google search gives 40 "formic acid" hits for every 1 "methanoic acid" hit. Walkerma 14:56, 16 February 2006 (UTC)
I agree on this one, IUPAC nomenclature should be preferred and used.HappyApple 03:57, 17 February 2006 (UTC)

atomic masses of Uuo (element 118) and Uus (element 117)

I asked this on their talk pages, but go not response. If the elements are undiscovered, how can they have atomic masses? Shouldn't they but just unknown until confirmed? Olin 13:42, 17 February 2006 (UTC)

The mass of protons, neutrons, mass defect and all that, are known, and there's no reason to believe such nuclei cannot exist. Nuclear properties such as stability can be deduced from systematic trends. There's only a narrow range of probable values, which ultimately even might give them a better uncertainty than for elements whose natural isotopic composition has been measured (I haven't checked that.)
They have to be somehow marked as uncertain values of course. Usually for elements of unknown composition the mass number of the most stable isotope is given in square brackets. It's not meant as a statement as to whether anything of it has been experimentally verified, which is all relative in any case. According to the data from Audi et al. for example, still as of 2003 all isotopic masses of lawrencium are at least partly derived from systematic trends. Femto 15:52, 17 February 2006 (UTC)
Fair enough, but they should definitely be marked as unknown. Furthermore, the Uuo page has two different masses, albeit one is from the retracted reaction. And don't they at least know then number of neutrons??? Olin 21:18, 17 February 2006 (UTC)
I changed them to give a precise mass for one specific isotope and include a "predicted" qualifier. Femto 15:01, 18 February 2006 (UTC)

Chemical Education

In working through creating articles on chemistry journals, I generated a redlink for chemical education. This surprised me and a search that found nothing surprised me more. Am I missing something? If not, do people have ideas about what might go into such an article. I'll then have a go at starting it. I think we need one. Of course, if someone else wants to go for it, then go for it. --Bduke 02:25, 18 February 2006 (UTC)

Wow, amazing! Last year I was surprised that there was no Category:Chemical education (there is now), but I didn't realise there was no article on the topic. You should definitely have a go at writing one, I'll try and help. Or maybe we should have it as a first Chemistry COTM? Walkerma 03:09, 18 February 2006 (UTC)
Yep, I found the Category after writing the above. There is an article Science education and one on Physics education so we definitely should have one. Looking at other COTMs it seems some have difficulty in finding articles and it does not mean much when they do. Is there a move towards a Chemistry COTM? I'll think about the article, but off to a Cider tasting very soon! --Bduke 03:42, 18 February 2006 (UTC)

I have created Chemistry education as a brief stub. Will add to it later, but please add to it now. Chemical education redirects there. It needs work, but I think it is already better thab Physics education. --Bduke 00:21, 20 February 2006 (UTC)

Comments on "amine" needed

I have recently added some sorts of data into the article amine. This is my first major edition to a chemistry article, and I am not sure that whether there is any misconceptions. May anyone see if there is any problems? Ray Leung 18:55, 19 February 2006 (UTC)

Nice contribution. I made stylistic edits. On a point of style, it is debatable if element names should be pluralized: "If two of the hydrogens" vs. "If two of the hydrogen atoms". Also, students tend to view water solubility as a black-white thing, but it is of course relative. Few molecular organic compounds can legitamately described as being insoluble in water (otherwise our pollution problems would be less severe). I dont know the official Wiki view on "alcanols", which you refer to, but I can report that few practicing chemists on this planet use the term. If you feel that my changes were too drastic, we can discuss this on the amine talk page.--Smokefoot 20:04, 19 February 2006 (UTC)

Wasn't "alkanol" an attempt by IUPAC to bring the nomenclature of functional groups inline with alkanes and such? I remember reading about it in some article on Chemistry education (along with cousins "alkanal" and "alkanone") but apparently didn't catch up, so I think it's not used anymore... -- Rune Welsh | ταλκ 20:47, 19 February 2006 (UTC)
    • It was used as a normal term in my university nearly two decades ago, and I still think many people in chemical industry a familiar with the term, especially in a chemical/theoretical context, like writing chemical reactions on the whiteboard. Ps this doesn't mean that we don't use the world alcohol, but that's more for the stuff in the Glenkinchie bottle. Wim van Dorst (Talk) 21:24, 19 February 2006 (UTC).
Ok I concede, maybe the alcanol is an industrial thing - not my world - I never see it in my work, although I would know what it is. What about my comment on plurals of elements?--Smokefoot 21:54, 19 February 2006 (UTC)
One comment: Sometimes R with a subscript number looks like multiple R groups (R2 as two R's). It's probably not worth changing all of your diagrams though. Olin 21:59, 19 February 2006 (UTC)
  • I have just edited the section "Reaction" and "Uses of amine & derivative". May any experts proofread it for me? Thanks a lot! Ray Leung 05:42, 20 February 2006 (UTC)

acid and bases pages

As a whole, there is a lot of redundancies on pages about acids and bases, and many of them need work. I did some on acid the other day. Some of the pages include the following: acid, base, strong acid, strong base, weak acid, weak base self-ionization of water, pH, acid dissociation constant, acid-base reaction theories, polyprotic acid, neutralization, Bronsted acid, Brønsted-Lowry, Lewis acid, Lewis base, buffer solution and Henderson-Hasselbalch equation.

I realize it's OK to have duplication, but some of it is annoying to me, at least. Ka is defined at least three different times, and pH is defined at least three times. The Ka's for a polyprotic acid (Ka1, Ka2, etc.) are defined at acid, but not under acid dissociation constant or polyprotic acid. The Arrhenius, Bronsted-Lowry, and Lewis definitions are given at acid and acid-base reaction theories (the latter has two additional defintions), as well as at Bronsted acid, Brønsted-Lowry, Lewis acid, Lewis base (where appropriate). Also, "acids and bases" redirects to pH whereas "acid-base" redirects to acid-base reaction theories. There's a category acids and a category acid-bases, most of which have nothing to do with each other.

I'm not sure how much time I'm going to have in the next few days, but any movement toward clean-up or suggestions for clean-up of these articles as a whole would be appreciated. In some ways, I think it'd be good to have one article with good linking (or some consolidation, at least), but I suspect that would be disfavored by wikichemists judging from previous discussions. Olin 01:53, 20 February 2006 (UTC)

  • A related problem exists for, say, hydrogen bromide and hydrobromic acid, where a discussion has commenced apparently on a merger. I guess this problem applies mainly for HF, HCl, HBr, and HI, but we encounter a related issue with the overlap of arsenic(III) oxide and arsenous acid. As noted by others, articles often exist for anions and their conjugate acids, which can lead to some duplication: cyanide, HCN, NaCN, and KCN.--Smokefoot 20:34, 26 February 2006 (UTC)

hydrogen bromide and hydrobromic acid This page need some native speaker! The platnum is the one I will fix. Links and the merge wit a redirect would be a good idea.Stone 20:52, 26 February 2006 (UTC)

Regarding merges on pages like hydrogen bromide and hydrobromic acid, I think we need to consider the importance of each form, and also how much difference there is. In the case if HBr and HI, I think they are both important enough to warrant separate pages, just like with HCl. There are many organic procedures using hydrobromic and hydriodic acids, for example. However when writing material for vanadium(V) oxide, I included some chemistry of "vanadic acid", because the latter is unlikely ever to have a separate page (though vanadate may end up with a page, rather than a redirect). Each case needs to be judged on its own merits. I think Olin's comments on acid/base pages in general are warranted - there is a lot of duplication, and cleanup is definitely needed. We probably need to keep separate pages for distinct topics like Lewis acid, though, with that nice article list/box to guide us. Walkerma 14:10, 27 February 2006 (UTC)

Oil (liquid)

I would like to invite interested wiki-chemists to help edit the article Oil (liquid) with their knowledge about this mysterious substance. While formatting the Oil disambiguation page, I noticed that an article describing oil in general seems to be missing (I do hope that I am wrong). I created a stub from interwiki sources, but help from experts is very welcome. -- Ravn 19:56, 26 February 2006 (UTC)

Maybe I am too prickly, but the article begins with the comment that an oil is a "chemical substance" - do substances exist that are not "chemical"? (does anything exist that is not chemical, but again maybe such views are excessively pedantic0. My own worry about oil is that the topic is, well, amorphous. Probably someone official has decreed that oil must have such-and-such a threshhold viscosity, end of story unless one aims to write about liquids of certain viscosities. --Smokefoot 20:20, 26 February 2006 (UTC)
An oil is usually hydrophobic as well (oil of vitriol is a notable exception). Seems enough there for a stub. Physchim62 (talk) 22:46, 26 February 2006 (UTC)

"Chemistry World" piece

FYI: This project gets a mention in the chemical press! Take a look at http://www.rsc.org/chemistryworld/News/2006/February/24020602.asp I apologise to folks for the "vandalism challenge", that was supposed to be an aside to the writer only - I hope that most chemists will be responsible enough not to take up the challenge! I was merely trying to indicate that most vandalism is well under control. By the way, I don't believe that Wikipedia will replace Chem Abs/Scifinder, though the article might read that way. But I do think Wikipedia will replace the Aldrich catalogue, the Merck Index, the "Rubber bible", the Chemists' Companion, and maybe even March and Greenwood/Earnshaw as one single source of general chem info and lead refs. I think it will stir up some discussion about Wikipedia as a source of chemical information, though, and we need to realise, the (chemical) world is watching what we do! Walkerma 17:17, 27 February 2006 (UTC)

This will help as long as some of them get up and contribute to the project. Most of the stuff in literature like synthesis and analytical data is ideal for wikipedia. For most of the world the terrible expensive journals are not availabel, and wikipedia information is free for everybody. Sometimes I which I could edit articles in the good journals like a article of wikipedia. But a NPOV tag to it, writte a comment that the synthesis does not work, or that the interpretation of the analytical data is wrong, or that the old articleis now substituted by a better one. But we can use all help we can get, and the vandales died out hundreds of years ago and with the few survived in the net we can handle.Stone 19:43, 27 February 2006 (UTC)
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