Wikipedia talk:WikiProject Chemistry

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WikiProject Chemistry (Rated Project-class)
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Discussion of the WikiProject Chemistry - Please add your comment and discussion here. Older discussions are archived.


This discussion page is about the Chemistry project itself, for detailed, in-depth discussions about specific topics, you'd be best served at the talk page of the specific subject, e.g., Chemicals, Chemical infoboxes, etc. There is also an image request page which might be of interest to you.


Image issues in captodative effect[edit]

This article has been submitted to DYK and I have been asked to look at it, which I am doing (obviously). I realize there are some issues, I haven't made changes yet, but I would like to ask for a couple of specific pieces of help:

  1. The article includes the image File:General Reaction Scheme.png, which has the following issues:
    • the name is not descriptive, but that can only be addressed by a COMMONS admin, I think
    • the aryl-sulfur bond angle is off, as is the positioning of the radical dots. The '+' could stand being bigger, too... maybe it would be easier to redraw it, and also make either both R's red or neither. In the context of the article, I am not sure why the R is highlighted or why the nitrile is a CN in the starting material but with bonds shown in the product.
  2. There are two images near the end of the article, File:Solvent Affinity effects of substituents.jpg and File:Polar effect.jpg, each also needs a new name. However, looking at them in the article, they look to me to be scanned from somewhere in which case there is a copyvio issue here. Each could easily be redrawn.
  3. File:Resonance contributors of 2-(dimethylamino)propanenitrile.jpg should probably be "Resonance contributors of 2-(dimethylamino)propanenitrile radical" and could use some improvements in drawing, charges in circles, clearer radical dots, etc.
  4. None of these are SVG's, which would be better, obviously.

To address a couple of obvious questions, the editors who updated the article are students working on a now-finished class project, so are likely not returning (neither has edited since November 12). And, my access to structure drawing software won't be back until next year, so I can't do the drawing. Input from the students (@DgsinUM, Genger14:), the course-related editors (@ChemLibrarian, UMChemProfessor:), their online ambassador (@Graeme Bartlett:) and the DYK reviewer (@Yoninah:) are welcome, obviously. EdChem (talk) 00:22, 17 December 2013 (UTC)

The topic defines itself as an effect involving radicals and a stability that presumably makes certain structures easier to access (if an intermediate, then lower-energy barrier so a faster reaction). But many of the reactions discussed in the "Uses in synthesis" section (Friedel–Crafts and Diels–Alder) are not generally considered to be radical mechanisms and the given reactants are full-octet and in the ground state. Either the topic is mis-defined (too narrow scope) or there is a major part of the logical progression missing. DMacks (talk) 03:00, 17 December 2013 (UTC)
I agree... I am planning to expand the intro because the effect can be seen in radicals but also in Diels-Alder and other cases where there is a synergistic interplay between an electron-donating and electron-withdrawing group. I took a while to figure out whether the last section was irrelevant or the topic drawn as a single case of a wider phenomenon, and concluded it was the latter. The peer reviews on the talk page somehow managed to miss this flaw. EdChem (talk) 07:41, 17 December 2013 (UTC)

Just clarifying, regarding the two diagrams that I speculate might be scanned and copied, I am wondering if anyone recognises or has a suggestion regarding the source. @EdJohnston: I note that you mention on the DYK nomination page that you have some of the sources as PDFs, can you see if the diagrams I mentioned above might be borrowed? EdChem (talk) 07:41, 17 December 2013 (UTC)

I was able to check all the but the last two images for copyvio and left a note at Talk:Captodative effect#Sources for the figures. The two images that were called out above as looking to be 'scanned from somewhere', File:Solvent Affinity effects of substituents.jpg and File:Polar effect.jpg, are definitely in the clear. It seems to be possible to change the names of Commons files if there is a good reason. Someone could do the move and say 'Per enwiki DYK review'.
@EdChem: In your point #1 you mentioned a need to improve the two diagrams in 'Substituent effect on reaction rates'. The material to back those images comes from our article's Reference 4, Osamu Ito et al (1988). I can provide the PDF of Ito's paper to anyone who will send me an email. If we are going to redraw diagrams somebody should fix the misspelling in 'Friedel Cfraft' in the last image.
@DMacks: The use of captodative terminology in connection with Friedel-Crafts and Diels-Alder appears to come from the cited sources. See one of the abstracts here. The word captodative is in the paper title, though I don't see where the radicals come in. We must be using a wider sense of captodative that is not just for radicals. So EdChem's point about the 'wider phenomenon' must apply. EdJohnston (talk) 22:38, 23 December 2013 (UTC)
@EdJohnston: electron-rich dienes do not generally undergo Diels-Alder reactions readily. It turns out the captodative olefins are much better dienophiles, attributed to a transition state close to the diradical and similarly stabilised. I have added to the article to make the points being made clearer. EdChem (talk) 14:52, 8 January 2014 (UTC)

Thanks for the comments and suggestions. I will contact the students personally to see if they are willing to make some of these changes. UMChemProfessor (talk) 17:53, 22 January 2014 (UTC)

Royal Society of Chemistry Event[edit]

On 28 March 2014 the Royal Society of Chemistry and Wikimedia UK are holding an event in London aimed at giving members of the RSC an introduction to editing Wikipedia and spending some time creating or improving articles related to chemistry. Details are at wmuk:Royal Society of Chemistry 2014 Event.

This is a heads-up for WikiProject Chemistry that some activity may take place in mainspace (although I will encourage new editors to use their sandboxes to start off). It is also an invitation to suggest topics that you feel that members of RSC could usefully contribute to; and an invitation to join us online 14:00–16:00 by collaboratively editing (an IRC channel will be available, possibly conferencing via Mumble or Skype).

It would be encouraging to have members of WikiProject Chemistry get involved; building relationships with the Royal Society of Chemistry would be valuable for all. Cheers --RexxS (talk) 22:13, 19 December 2013 (UTC)

This is a much-needed initiative. Where will the meeting take place?
For some years now I have been trying to bring WP chemistry articles up to a professional standard - see my home page for details. However, it will be hard to justify the expense of a trip to London for this event. P.S. I retired from the RSC many,many years ago! Petergans (talk) 10:17, 23 December 2013 (UTC)
For this initial event, the RSC are selecting 20 members to be trained in person at Burlington House, London, and I'm going to be concentrating on making sure that they can edit with a minimum degree of competence. So I've simply suggested that interested Wikipedians might like to join us remotely during the afternoon, either via an IRC channel or by editing articles with us. I think your Wikipedia skills will be well beyond what I am targeting for the event, but we'd love to see you get involved remotely on the 14:00–16:00 session if you are able - do check for more info as it becomes available. If this event goes well, I'm keen to see similar sessions take place throughout the UK, so perhaps we can keep in touch and create an event near you? Cheers --RexxS (talk) 19:01, 23 December 2013 (UTC)
I won't be anywhere near UK, but can almost certainly join online via IRC, etc. DMacks (talk) 19:17, 23 December 2013 (UTC)
I just checked freenode, the #wmuk-rsc connect channel does not appear to exist:( DMacks (talk) 14:34, 28 March 2014 (UTC)
  • I expect (... well, hope) to be in work that day, but I'm happy to help outside of working hours should at be of any benefit. You might also want to try contacting User_talk:Andeggs, they're not particularly active, but they are affiliated with the Royal Society. I believe they have a Wikimedian-in-Residence, perhaps you could combine resources? Project Osprey (talk) 00:43, 4 January 2014 (UTC)

European Commission number[edit]

What shall we do with this edit/information? --Leyo 01:22, 5 January 2014

Nobody? --Leyo 21:23, 9 January 2014

AfC submission[edit]

Another one for you guys. Regards, FoCuSandLeArN (talk) 14:56, 12 January 2014 (UTC)

A good topic for an article! I added some comments. A question for WP:CHEM, the related structural classes "helicene" and "acene"" are at the singular pagename whereas this is proposed at the plural "phenacenes". What's the naming MOS? DMacks (talk) 19:44, 12 January 2014 (UTC)
According to WP:SINGULAR, article titles should generally be singular, unless the dominant usage is plural, e.g., statistics. --Mark viking (talk) 20:06, 12 January 2014 (UTC)
More relevantly, Wikipedia:Naming conventions (chemistry)#Organic functional groups and related compound classes says singular. DMacks (talk) 05:05, 13 January 2014 (UTC)
I appreciate your input! Here's one more. Cheers, FoCuSandLeArN (talk) 21:23, 12 January 2014 (UTC)
Commented. Might want to ask at Wikipedia:WikiProject Mathematics or something as well. DMacks (talk) 10:27, 20 January 2014 (UTC)
For metachirality? Or do you mean the Esbjerg one? FoCuSandLeArN (talk) 18:42, 23 January 2014 (UTC)
Metachirality. Although it describes an application to chemistry, the idea of symmetry is broader than that (spatial transformations/relationships), at least two of its refs are specifically to math literature (although used to support some chemistry). DMacks (talk) 18:19, 24 January 2014 (UTC)
And yet one more. FoCuSandLeArN (talk) 00:09, 17 January 2014 (UTC)
Commented. DMacks (talk) 10:27, 20 January 2014 (UTC)

Proposal to split octanol[edit]

I propose that we split octanol. The area is topical because of 4-Methylcyclohexanemethanol, which is an octanol isomer. Most organic and pharma people are interested mainly in 1-octanol. The biosynthetic world is mainly into the 1-isomer too, I think. The commercially most important octanol is 2-ethylhexanol. The split would generate self-standing 1-octanol and an article "octanols". I have already started tidying links that are specific to 1-octanol vs any old octanol. The change would involve shifting certain information from octanol to 1-octanol, which is now a redirect. Please leave concerns here. --Smokefoot (talk) 18:25, 16 January 2014 (UTC)

The idea seems reasonable to me. Small quibble, though... 4-methylcyclohexylmethanol is an isomer of octanal (C8H16O), not of octanol (C8H18O). EdChem (talk) 22:22, 16 January 2014 (UTC)
Oh, that is a good point about the isomers. Yikes. --Smokefoot (talk) 23:15, 16 January 2014 (UTC)
Splitting and organizing the octanols that way sounds good to me too. (And I wouldn't worry too much about the strict definition of isomers - cyclohexanol is often referred to as a hexanol, for example, even though it's not exactly a constitutional isomer.) -- Ed (Edgar181) 23:52, 16 January 2014 (UTC)
I would worry about the "strict" definition of isomer if I was "you" or else your just going to have to go and fix it later. (talk) 05:46, 17 January 2014 (UTC)
And how is this remark helpful, dear Both the strict definition and the common use should be mentioned, we are writing an encyclopedia here. --Dirk Beetstra T C 07:39, 17 January 2014 (UTC)
I am saying that MCHM etc should not be put in the category of isomers of 1-octanol etc, as I think Edgar is suggesting. Do you disagree? (talk) 10:36, 17 January 2014 (UTC)
Well, I can't read that in any form in Edgar's remark. --Dirk Beetstra T C 10:43, 17 January 2014 (UTC)
Ok, on closer inspection he seams to be consoling Smokefoot (sorry Edgar181). What exactly do you think again? (talk) 10:52, 17 January 2014 (UTC)
Sorry if I wasn't clear. I just meant that it's perfectly reasonable to mention MCHM in a discussion of octanols, even though it is not, strictly speaking, an isomer. Just like cyclohexanol is mentioned at hexanol, but not included in the list of isomers there. -- Ed (Edgar181) 00:56, 18 January 2014 (UTC)
Yes when discussing physical/chemical properties of related compounds (that are not isomers)(I am not sure what the proper word is). As long as some people don't get the wrong idea. I think I think this is what Beetstra thinks. (talk) 01:20, 18 January 2014 (UTC)

Article-title of a "name" reaction[edit]

Would like help deciding whether to use the generic structure/reactivity type of name vs the name reaction for the article title: Talk:Nitroaldol reaction#Primary name of this topic. I don't see anything in CHEM MOS about this issue. DMacks (talk) 10:04, 20 January 2014 (UTC)

My advice would be to enter the two names into a literature seach engine and see which gives the most hits.Project Osprey (talk) 10:47, 20 January 2014 (UTC)
I would say that we need a bit of guidance from a MOS here, just as we do with chemical names. The first one DMacks mentions is sometimes difficult to name, whereas the second one is often 'easier'. Finding 'counts' for the first may also be difficult as the terms may be slightly different throughout. I would say that if the name of the name reaction is independently sourceable to one of the more respectable name-reaction-compendiums/glossaries, the article should be there, and all possible redirects pointing to that article. If the name is not there yet, leave it and try to use the reactivity-type name. Thoughts? --Dirk Beetstra T C 03:59, 21 January 2014 (UTC)

Nathaniel Thomas Lupton, State Chemist of Alabama and early Professor of Chemistry in the US[edit]

Hello. I would greatly appreciate it if some of you wanted to expand the page of Nathaniel Thomas Lupton, State Chemist of Alabama after the American Civil War and early Professor of Chemistry in the US. Please do add a reference/citation for everything you add. Thank you.Zigzig20s (talk) 20:51, 20 January 2014 (UTC)

New article, potential conflict of interest[edit]

Dear Wikichemists,

As an active editor of Wikipedia chemistry articles until recently (my PhD is taking up most of my time these days), I've been asked by some academics in my department to help them create a WP article about their outreach activities. Having seen numerous CoI cases discussed on this page, I am wary of creating articles so close to me. Having said that, the draft I have been given is pretty factual and lacking in hyperbole, with references to peer-reviewed science education journals and government websites, and it is easy to verify independently that my department is a world leader in science outreach.

What's the best way to proceed? As I see, the options are (1) don't create the article to be sure of avoiding CoI; (2) get input from others while drafting (i.e. what I'm doing now); (3) edit the draft carefully for neutrality, then publish and hope any CoI is edited out by others; or (4) start a related but more general article instead.

Ben (talk) 19:07, 21 January 2014 (UTC)

(5) throw it in the general direction of Wikipedia:Articles for Creation? (create it there, notify us here of the page, but let primarily non-chemists have a look at the case? Your CoI does not seem very strong (not more than a couple of beers and a pat on your shoulder?), and you are frank and open about it, but it is best to have it independently looked at before it ends up in mainspace. --Dirk Beetstra T C 20:05, 21 January 2014 (UTC)
(maybe also declare your CoI at the AfC, you don't want to throw away your chances to become an Arbitrator one day .. ;-) .. good luck with the thesis, 'send' us a copy). --Dirk Beetstra T C 20:07, 21 January 2014 (UTC)
Thanks for declaring your potential COI. One avenue not mentioned is to create the article at AfC and solicit for AfC comments from independent editors here at WP Chem. As an experienced editor, you don't need the hand-holding of course, but it is a common mechanism for uninvolved editors check neutrality and notability of articles with COI issues before releasing to mainspace. Soliciting for comments here will hopefully speed things along. --Mark viking (talk) 20:10, 21 January 2014 (UTC)

Thanks for the tips, guys. Will do AfC as you suggest. Ben (talk) 22:36, 21 January 2014 (UTC)

The draft is at Wikipedia talk:Articles for creation/Bristol ChemLabS for now. I will finish editing and formatting it later, so you can look now or wait until it's a bit more readable. I'll post a note here when it's ready. Ben (talk) 14:45, 27 January 2014 (UTC)
The article is now formatted and ready for any comments you may have. Cheers, Ben (talk) 10:16, 30 January 2014 (UTC)

Wikipedia:Help desk#Checking for copyright problems in hidden edits[edit]

Dear chemistry experts: Could someone here please check the two articles being discussed at the above Help Desk thread and give an opinion as to whether the mainspace article can be merged with the Afc article and the result moved to mainspace? Thanks. —Anne Delong (talk) 20:26, 22 January 2014 (UTC)

Wikipedia talk:Articles for creation/flow miniplant[edit]

Dear chemists - Is this old abandoned Afc draft a notable topic, and should the article be preserved? —Anne Delong (talk) 23:04, 24 January 2014 (UTC)


I came across the term complex in article Gintonin but could find no obvious place to point it. Complex is a disambiguation page which lists several specific types of complex, none of which seem to fit the bill, but there is no single article that explains in more general terms what a complex is in a chemical sense. From a layman's perspective I think that this term, or probably Complex (chemistry) needs an article of its own. --Derek Andrews (talk) 12:34, 27 January 2014 (UTC)

Closest I could find is indeed Multiprotein complex (though here not multiprotein, but protein and 'small molecule' complex). The use of the word 'Complex' is complex throughout chemistry - an inorganic chemists will look at it from another side than a biologist (and the same for ligand, which is almost swapped around in meaning). You may want to attract some people from the biochemistry or pharmacology-corners of Wikipedia here as well, they may be more capable in this corner of chemistry. --Dirk Beetstra T C 12:44, 27 January 2014 (UTC)

AfC submission[edit]

Another one coming your way. Thanks, FoCuSandLeArN (talk) 20:49, 27 January 2014 (UTC)

I thought you might be interested in this biography. FoCuSandLeArN (talk) 13:25, 4 February 2014 (UTC)
And this one. FoCuSandLeArN (talk) 21:40, 12 February 2014 (UTC)

Merge proposal: Organofluorine compound into Organofluorine chemistry[edit]

A merger that is probably non-controversial: Organofluorine compound into Organofluorine chemistry (or the reverse). The discussion is here. --Smokefoot (talk) 17:44, 2 February 2014 (UTC)

Archived some threads[edit]

I've archived some inactive threads to subsections which were notifications about discussions that have since been closed. — Cirt (talk) 18:52, 5 February 2014 (UTC)

Wikipedia talk:Articles for creation/Diarylide Yellow[edit]

Dear chemists: This old abandoned Afc submission is about to be deleted as a stale draft. Is this a notable topic (and is it a chemistry topic) and should the article be saved? —Anne Delong (talk) 00:48, 8 February 2014 (UTC)

Rescued: Diarylide pigment. Thanks for identifying these articles. This is an good one. --Smokefoot (talk) 04:56, 8 February 2014 (UTC)
I thought it might be! That's one more off my list. Thanks! —Anne Delong (talk) 05:48, 8 February 2014 (UTC)

Red rot[edit]

red rot is the leaching of zinc from brass via acidic reaction. This content was split to red rot (brass) which was deleted for copyright problems. We have an article called red rot (leather) which is misplaced if there's no brass article. Can someone create an article on brass redrot, and then rebuild the disambiguation page? there was a wood redrot noted previously for the third article. -- (talk) 19:54, 9 February 2014 (UTC)


Is ferrocyanide dangerous if used on my face in eye makeup? — Preceding unsigned comment added by Julievp (talkcontribs) 15:02, 10 February 2014 (UTC)

Dear wikipedians,

The article on the bergius process states that 97% of the coal feedstock can be converted to usable petrolium. Is this by weight or volume?

Is the figure for consumed hydrogen correct? (talk) 19:01, 13 February 2014 (UTC)Keith

IUPAC vs Common Usage[edit]

Dear Chemistry WikiProject, Is there any sort of consensus as far as what to do in instances where an IUPAC convention directly contradicts common (scientific) usage? This issue seems to come up often, especially in regard to molecular weight and polydispersity related articles. Thanks. (+)H3N-Protein\Chemist-CO2(-) 17:12, 14 February 2014 (UTC)

The consensus is to go with common usage over IUPAC. Often articles mention IUPAC, especially if it seems to be gaining some acceptance. Often we just ignore IUPAC. The common usage vs IUPAC thing is a source of frustration to nonchemistry editors who often seem to think that chemists should follow these rules more assiduously, as you can see in a long conversation higher up on this page.--Smokefoot (talk) 19:15, 14 February 2014 (UTC)
Ok. Thanks. (+)H3N-Protein\Chemist-CO2(-) 16:40, 5 March 2014 (UTC)
It seems like a large number of people (mostly IP's) editing on behalf of IUPAC have decided to retcon most polymer related articles to label terms commonly used by current researchers and instrument manufacturers as "depreciated", "retired" etc. Dealing with this by myself is starting to get a bit tiresome, and it looks like the polymer wikiproject is mostly inactive. Any suggestions?(+)H3N-Protein\Chemist-CO2(-) 01:59, 9 April 2014 (UTC)
If there are questionable cases, then list them on this page. Start a new section at the bottom of this talk page. --Smokefoot (talk) 02:20, 9 April 2014 (UTC)

Low field NMR merger[edit]

I've posted this over at over at Wikiproject Physics and it was recommended I loop in Chemistry as well: there's a Start-class article at Earth's field NMR and stubs at Low field NMR and Zero field NMR. I'd like to take a crack at improving the coverage of this subject, and I think the best thing to do to start with is to merge all three articles together into the Low field NMR article, as Earth's field and Zero Field are both special cases of Low field NMR. I proposed the merger on the Zero Field NMR page about 2 years ago and have had no response, so I'm thinking I might go ahead and undertake the merge and redirect the other two. Any objections or suggestions? 0x0077BE [talk/contrib] 07:13, 17 February 2014 (UTC)

Thermal depolymerization & Hydrothermal liquefaction[edit]

AFAICT, Thermal depolymerization is a less-used synonym for Hydrothermal liquefaction. I left a note at Talk:Hydrothermal liquefaction#Merge. --Chriswaterguy talk 04:02, 18 February 2014 (UTC)

Popular pages tool update[edit]

As of January, the popular pages tool has moved from the Toolserver to Wikimedia Tool Labs. The code has changed significantly from the Toolserver version, but users should notice few differences. Please take a moment to look over your project's list for any anomalies, such as pages that you expect to see that are missing or pages that seem to have more views than expected. Note that unlike other tools, this tool aggregates all views from redirects, which means it will typically have higher numbers. (For January 2014 specifically, 35 hours of data is missing from the WMF data, which was approximated from other dates. For most articles, this should yield a more accurate number. However, a few articles, like ones featured on the Main Page, may be off).

Web tools, to replace the ones at tools:~alexz/pop, will become available over the next few weeks at toollabs:popularpages. All of the historical data (back to July 2009 for some projects) has been copied over. The tool to view historical data is currently partially available (assessment data and a few projects may not be available at the moment). The tool to add new projects to the bot's list is also available now (editing the configuration of current projects coming soon). Unlike the previous tool, all changes will be effective immediately. OAuth is used to authenticate users, allowing only regular users to make changes to prevent abuse. A visible history of configuration additions and changes is coming soon. Once tools become fully available, their toolserver versions will redirect to Labs.

If you have any questions, want to report any bugs, or there are any features you would like to see that aren't currently available on the Toolserver tools, see the updated FAQ or contact me on my talk page. Mr.Z-bot (talk) (for Mr.Z-man) 04:58, 23 February 2014 (UTC)

Article: Carbonite (ion)[edit]

I'm not that pro, but the reaction equation seems highly suspicious. Could anyone please check whether the recent contents (in particular this section) be hoax? Thank you.

If I post this at the wrong place for discussion, please move it to the proper place. --- SzMithrandir (talk) 04:14, 24 February 2014 (UTC)
I've removed the offending section. I'm not sure what "exposure to oxcidising [sic] leads to a breakdown in the melectural [sic] structure" was supposed to mean, and since it was unsourced I had no way of untangling it. The equation didn't have arrows, so I don't know if the equals sign was supposed to be a double bond or what. Maybe the editor who added it will come up with a source eventually and we'll be able to figure out what he means by metamorphicity/metamorphia. 0x0077BE [talk/contrib] 04:48, 24 February 2014 (UTC)
Judging from the contribution histories of the IP and the registered account, and the latter’s Talk page, I doubt any source exists. (I’ll refrain from further comment.) I observe that the subsection has already been restored once after being reverted.—Odysseus1479 08:00, 24 February 2014 (UTC)

:) OK. we'll see. -- SzMithrandir (talk) 06:32, 24 February 2014 (UTC)

Is it bad that you get to a stage, that when you look at a page and the first section is a discussion on its various systematic names followed later by a section on the amphotericity; and you think: I know who's been editing this. On a somewhat related note, this is a carbenoid right? (it's not just me being groggy in the morning?) because the page doesn't make that statement anywhere, but it does say its an ion. Project Osprey (talk) 10:13, 24 February 2014 (UTC)

I note that the article includes this:

The carbon centre in carbonite can bond with electron-donating molecules by reacting:
CO22− + R: → RCO22−
Because of the capture of the nucleophile (R:), carbonite has acidic character.

Am I the only one that doubts this? An uncharged "R" would necessarily be a radical, and a lone pair attack from a nucleophile on an anion like CO22− is not chemically reasonable. Carbonite cannot be a B-L acid (obviously) and would not be a Lewis acid if its structure is [:C(=O)-O:]2− with complete octets on all three atoms. To me, much more likely is:

CO22− + E+ → E-CO2still

Thoughts? EdChem (talk) 10:49, 24 February 2014 (UTC)

  • I believe the issue of amphotericity has previously been raised with regard to Methylene_(compound); it gained little traction there either. I'm sure most would agree that radicals are neither acidic nor basic nor both-at-once; they have their own behaviour. With that in mind I think the content should be re-written from the standpoint of normal radical chemistry. Trying to push the definition of basicity into into brave new territory is likely going to confuse everyone. Project Osprey (talk) 18:39, 24 February 2014 (UTC)
Since the article's foundations are shakey, why dont we condense it and turn it into a redirect to dihydroxymethylidene (aka dihydroxylcarbene), its conjugate acid? --Smokefoot (talk) 12:52, 24 February 2014 (UTC)
A reasonable argument. The pages do use the same references. Project Osprey (talk) 18:39, 24 February 2014 (UTC)
Excellent idea! And prune away the lewis acidity its just PPlain weird. A more PPlausible speculation would have been Lewis base behaviour like the isoelectronic nitrite ion. Axiosaurus (talk) 18:35, 25 February 2014 (UTC)

I would suggest the article on the carbonite ion / dihydroxymethylidene be deleted entirely.


1. The three references cited do not mention in their abstracts (all I can access) anything but alkali metal/carbon dioxide complexes observed in the gas phase. Assigning charges to the components (i.g. CO22+) and thus declare them to be ions is plain nonsense without demonstrating that these components will move in opposite directions once an electric field is applied. Quite the opposite, bond angles are quoted of around 130 degrees, and that the molecule forms a ring. With these statements, claims of ions are counterindicated, and all that may be claimed is a dipole: the molecule can orient in an electric field, but not move! For comparison, consider CH3Cl. Is that made of ions even if called methylchloride?

2. There is no mention of hydrogen in the compounds observed. To derive from the observations reported that HO-C-OH exists is jumping the guns. Provide the experimental evidence first, please!

3. If we assume that HO-C-OH should exist, then the bonding angle O-C-O must be 180 degrees, otherwise it would immediate isomerise into formic acid via rotation of the OH groups. 180 degrees bonding angle implies the presence of two pi and one sigma bond on the carbon as in acetylene, they may be stiff enough to hold at a very low temperature, but at gas-phase temperatures? Please, show me that an en-ol reaction does not take place, creating again formic acid!

4. And radicals? I have never heard of a two-electron radical! My training in chemistry has emphasised that a radical is a compound with a single (unpaired) electron. It is so reactive that median life-expectancy for it is in the order of milli- or microseconds. Two unpaired electrons would constitute a highly exited compound, which would near-instantaneously combine into an electron pair, with the opposing spins that pair formation implies.

Get rid of Dihydroxymethylidene asap! Or cite sources that do claim they have observed it!

W-o-f-o-w (talk) 12:27, 18 March 2014 (UTC)

AfC submission[edit]

Wikipedia talk:Articles for creation/Hantz reactions. FoCuSandLeArN (talk) 20:16, 25 February 2014 (UTC)

Help a new user on an article[edit]

I haven't a clue where to begin helping on Octene-3-yl acetate. I don't even think that is the correct name. Bgwhite (talk) 06:43, 26 February 2014 (UTC)

It's not the best name for it 1-Octen-3-yl acetate would be better, but I don't believe you can have page names which start with numbers. It's a terpene ester present in lavender oil, although at quite a low concentration (0.65% according to our page). It seems to have good commercial availability, with applications in perfumery; google indicates it has an 'Earthy, Fresh, Green, Herbal/ Herbaceous' smell. So it's a real thing with real uses, however it is rather niche. I'm wondering if the others feel its sufficiently notable to warrant a page? Project Osprey (talk) 10:10, 26 February 2014 (UTC)
I've done some tidying and moved the page to 1-octen-3-yl acetate. EdChem (talk) 11:33, 26 February 2014 (UTC)

The page was created by Gmongell who also created a page on 3-isobutyl-2-methoxypyrazine (current version) and also the page on lavandulyl acetate. According to his user page, Guy is a doctoral student at Case Western and has made a total of 19 edits, so he could be a good contributor for chemistry content but is very much a new editor (even though he registered in 2010). I think there are two approaches needed, one on the articles and one on supporting a new chemist. EdChem (talk) 10:41, 26 February 2014 (UTC)


Dear chemistry experts: While reading over this old Afc submission: Wikipedia talk:Articles for creation/Schumacher Process which was declined for lack of independent sources, I came across this related article: Tribromosilane . Its one source is to a now unused domain name which had been used by company founded by Mr. Schumacher. Is this a notable chemical name? Some of the the search engine results give it an alternate name Silicobromoform. Is one of these names a trade name? Should the dead link be removed since it was not an independent source in the first place? —Anne Delong (talk) 11:32, 27 February 2014 (UTC)

I think Silicobromoform is likely an older naming convention, not a trade name. I don't hear much about silanes, but the modern name would be tribromosilane. I'm guessing silicobromoform is using the same naming convention that would call trichloromethane chloroform, as silicotribromoform is just chloroform with all the non-hydrogen atoms shifted down one place in the periodic table. I'll leave it to others to determine notability as I'm not too familiar with notability guidelines for chemical compounds. The fact that it's even got a common name like silicobromoform makes me think it's more likely than not to be notable. 0x0077BE [talk/contrib] 15:56, 27 February 2014 (UTC)
It seems that Boghog has been improving it. Thanks to you both. —Anne Delong (talk) 23:21, 5 March 2014 (UTC)

Total free access to Royal Society History of Science journals for 2 days on March 4th and 5th[edit]

As Wikipedian in Residence at the Royal Society, the National Academy for the sciences of the UK, I am pleased to say that the two Royal Society History of Science journals will be fully accessible for free for 2 days on March 4th and 5th. This is in conjunction with the Women in Science Edit-a-thon on 4 March, slightly in advance of International Women's Day, on Saturday March 8th. The event is fully booked, but online participation is very welcome, and suggestions for articles relevant to the theme of "Women in Science" that need work, and topics that need coverage.

The journals will have full and free online access to all from 1am (GMT/UTC) on 4th March 2014 until 11pm (GMT/UTC) on 5th March 2014. Normally they are only free online for issues between 1 and 10 years old. They are:

The RS position is a "pilot" excercise, running between January and early July 2014. Please let me know on my talk page or the project page if you want to get involved or have suggestions. There will be further public events, as well as many for the RS's diverse audiences in the scientific community; these will be advertised first to the RS's emailing lists and Twitter feeds.

I am keen to get feedback on my personal Conflict of Interest statement for the position, and want to work out a general one for Royal Society staff in consultation with the community. Wiki at Royal Society John (talk) 12:17, 28 February 2014 (UTC)


See Wikipedia_talk:Chemical_infobox#Improved_temperature_options_in_Chembox. -DePiep (talk) 00:22, 5 March 2014 (UTC)

Most active WikiProject Chemistry members[edit]

Dear WikiProject Chemistry,

who are the most active editors here?--Kopiersperre (talk) 23:02, 5 March 2014 (UTC)

Adding meso isomers to isomerism image[edit]


The following image is used a couple of important pages (Isomer, Stereochemistry, etc) and also seems to have been edited by a few different people; so I thought I'd best mention things here before I did anything. I think the image should be edited to include mention of meso compounds. I'm thinking of a box linked to both 'enantiomer' and 'diastereomer'. Comments anyone? Project Osprey (talk) 23:19, 9 March 2014 (UTC)

A suggestion worth considering. I fear that including this detail it would complicate the chart to make a specialized point. Alternative possibility is to create a new chart that deals with the particular situation of meso vs d/l to be used in that special case. My two cents. --Smokefoot (talk) 00:06, 10 March 2014 (UTC)


Silly question, but I seem to see it at times. Are any of these wrong?

  • X (a compound) is eliminated into Y (product) and Z (the leaving group) —it’s the most common form even though it sounds formulaic.
  • Z is eliminated from X —fairly common, makes sense. but correct?
  • X eliminates Z
  • Z eliminates from X

The latter two are very uncommon, but seen occasionally. --Squidonius (talk) 04:22, 12 March 2014 (UTC)

Gel point of #2 diesel[edit]

Would someone please check Gel point (petroleum). An edit in November 2011 by someone who made no other edits added "For #2 diesel this is usually around 17.5F", and that was later cleaned up to use {{convert}}. A new edit has changed it to 45 °F (and broke the convert template). I would revert 45 as it seems absurdly high, but I have no idea what "#2 diesel" is, let alone whether 17.5 °F is correct. A quick look around does not provide information that I can readily interpret. Johnuniq (talk) 06:09, 12 March 2014 (UTC)

experienced editors needed at Energetically modified cement[edit]

The article appears to be pretty much an advertisement to me, but I have little knowledge in the field and so invite any one with background knowledge to come take a look. Thanks! -- TRPoD aka The Red Pen of Doom 07:49, 18 March 2014 (UTC)

AfC submission - 17/03[edit]

Wikipedia talk:Articles for creation/Aluminium diethyl phosphinate. FoCuSandLeArN (talk) 13:12, 18 March 2014 (UTC)

I see you've offered some comments on this draft's talk page. As far as AfC's concerned, it looks as if it's ready for acceptance and post-mainspace edits. Could you confirm this? There's no use in making it linger at AfC when knowledgeable editors could be editing it as we speak. Thanks! FoCuSandLeArN (talk) 19:39, 31 March 2014 (UTC)

Silicon and hydrofluoric acid[edit]

Silicon is apparently not attacked by HF due to the formation of a surface layer of SiO2. If that is so, why does HF readily attack glass: SiO2 + 4HF → SiF4 + 2H2O? Sandbh (talk) 00:57, 22 March 2014 (UTC)

Wikipedia talk:Articles for creation/Hantz reactions[edit]

Hi everyone. This article at the dreaded Articles for Creation project is awaiting review. It hasn't had much attention, which I think is due to the fact it's really written for specialists of this subject. I hope someone from here can come by and review it. Thank you! SarahStierch (talk) 16:57, 23 March 2014 (UTC)

Total free access to Royal Society History of Science journals for 2 days on March 25th and 26th !!![edit]

As Wikipedian in Residence at the Royal Society, the National Academy for the sciences of the UK, I am again pleased to say that the two Royal Society History of Science journals will be fully accessible for free for 2 days on March 25th and 26th. This is in conjunction with the Diversity in Science Edit-a-thon on 25 March. The event is held by the Royal Society and there are currently a couple of places available, as well as online participation which is very welcome, as are suggestions for articles relevant to the theme of "Diversity in Science" that need work, and topics that need coverage.

The journals will have full and free online access to all from 1am (GMT/UTC) on 25th March 2014 until 11pm (GMT/UTC) on 26th March 2014. Normally they are only free online for issues between 1 and 10 years old. They are:

The RS position is a "pilot" excercise, running between January and early July 2014. Please let me know on my talk page or the project page if you want to get involved or have suggestions. There will be further public events in May, as well as many for the RS's diverse audiences in the scientific community; these will be advertised first to the RS's emailing lists and Twitter feeds. Wiki at Royal Society John (talk) 17:33, 24 March 2014 (UTC)

AfC submission - 24/03[edit]

Wikipedia talk:Articles for creation/Warren S. Warren. Notable academic? FoCuSandLeArN (talk) 23:00, 24 March 2014 (UTC)

He's certainly well-known within the NMR community, not that that means anything. I think he's notable at the very least because of #5 of WP:PROF, i.e. he holds a named chair at Duke. 0x0077BE [talk/contrib] 22:25, 1 April 2014 (UTC)

Wikipedia talk:Articles for creation/Miguel de la Guardia[edit]

Dear chemistry experts: This old Afc submission will soon be deleted as a stale draft. Is this a notable professor, and should the article be kept and improved instead? —Anne Delong (talk) 01:53, 4 April 2014 (UTC)

Wikipedia talk:Articles for creation/Salt-water batteries[edit]

Dear chemists: This Afc submission was declined because there is another article in mainspace, Salt battery. Should salt-water batteries have a separate article, and if not, is there content that should be transferred to the mainspace article from this draft? —Anne Delong (talk) 02:47, 15 April 2014 (UTC)

Don't have time to look deeply now, but I think the pre-existing item Anne means is Salt battery, which is a redirect to Molten salt battery. On their face, salt-water vs melted salt are different things. DMacks (talk) 03:18, 15 April 2014 (UTC)
Sorry, yes, I dropped a letter. For salt batter I would have notified the Food and Drink guys! I thought the two topics looked different, but I'm no chemist. I have postponed the deletion of the draft for six months. Is it properly referenced for mainspace, or does it need improvement?
From the content, it seems like they are describing a simple Galvanic cell or Electrochemical cell that uses salt water as its salt bridge. Maybe we can set up a redirect for Salt water battery to Galvanic cell or Electrochemical cell (I'm not sure which is more appropriate) if that's a common search term. 0x0077BE [talk/contrib] 14:55, 15 April 2014 (UTC)