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Stub sorting by Plasmic Physics

Today I noticed this request posted to Plasmic Physics' talkpage. The answer from Plasmic Physics is 'Deciding which ones are incorrect is your responsibility.', to which I replied 'No, deciding which ones were correct was your responsibility, Plasmic Physics.'

Communesin B

However, I had a look through his latest contributions, and there are over 100 stub-sortings going on in those edits. They contain edits like this one, where the {{organic-compound-stub}} is replaced by a single {{cycloalkene-stub}} (stub class proposed by Plasmic Physics about a week ago - see Wikipedia:WikiProject_Stub_sorting/Proposals/2014/January, there is a new proposal of today as well). Not only are these edits damaging Wikipedia (see below), they are sometimes plainly wrong (Communesin B has aromatic rings, not a cycloalkene ring - see IUPAC)

Plasmic Physics obviously does not understand how damaging classifying an organic compound into a strict subclass (he only adds it, even wrongly, to cycloalkene, it is, of course, also an alkene (or a diene), an amide, an amine, an epoxide, a spiro compound (and the already noted aromatic compound)). Note that it would be equally damaging to actually add this compound to all the stub-classes the compound 'would belong to', which here would be at least 6 (which becomes a silly list of stub-templates), and which would undoubtedly be subject to discussion (is it an alkene-stub or a diene-stub), and in any case it is utterly counterproductive to building this encyclopedia (the properties are not determined by the amide functionality alone, it is a combination of all functionalities - having it in amide-stub alone is then not helping).

Can I have some help in undoing this damage (although I think that Plasmic Physics should undo it himself), check if there is earlier damage that also needs reverting (I only looked at his last 100 edits, reverted a good number out of the last 50), and can we discuss how we prevent further damage to Wikipedia. Thanks. --Dirk Beetstra ^{T C} 07:21, 11 January 2014 (UTC)

The stub category is empty again - everything reverted. Not a single compound in there that was categorised as a cycloalkene was solely a cycloalkene (if at all) - about 150 totally unhelpful edits. --Dirk Beetstra ^{T C} 11:50, 11 January 2014 (UTC)

Firstly, I was told that multiple stub templates are perfectly acceptable. Calling stub classification 'damaging' is an overreaction. When classifying, the Kekule (canonical) structures were considered in preference. Plasmic Physics (talk) 12:02, 11 January 2014 (UTC)

2-Carbomethoxytropinone is a cycloalkene, according to this edit by Plasmic Physics

@Plasmic Physics: I have looked through some of the pages you changed the stub category and Beetsrta reverted, and I am yet to find one where I agree with you. Aromatic compounds (like these: cytochrophin-4 cysteinyldopa cyphenothrin 4-caffeoyl-1,5-quinide cicloprolol benfluralin asulam anipamil (2S,3S,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid and 2CBFly-NBOMe) are not cycloalkenes, and if you don't understand why then I suggest you are unqualified to do this type of categorising. Worse, Cases like 2-carbomethoxytropinone, illustrated at right contain no C=C bond in a ring, even in a formal Kekule sense - unless you want to argue about tautomerisation. The compound is a tertiary amine, an ester, a ketone, and a β-ketoester, so making an "organic compound" stub makes sense to me... if I had to use a single category, I would choose "ester" in line with IUPAC naming of the ester functionality as its principal functional group. I don't understand why you went on this re-classifying spree, Plasmic Physics, but I for one consider it disruptive and ask that you do not continue without consensus. EdChem (talk) 13:07, 11 January 2014 (UTC)

@EdChem: I have managed to find one where the edit refers to a cycloalkene, but even then the stub classification is unnecessary. Testem (talk) 10:59, 13 January 2014 (UTC)

The '2-Carbomethoxytropinone' article says that "A β-keto ester, 2-carbomethoxytropinone exists in equilibrium with its keto–enol tautomer." Therefore describing it as a cycloalkane is justified. Plasmic Physics (talk) 21:46, 11 January 2014 (UTC)

That is true even for common compounds like hydroxyethene and 2-hydroxypropene. Yet another reason why naming compounds is sometimes tricky, and need a proper reference (which often does not exist). (And no, you don't have consensus here to go around and tag all systematic names that you can find now). --Dirk Beetstra ^{T C} 04:32, 12 January 2014 (UTC)

Don't take it there, the tagging has nothing to do with this. Plasmic Physics (talk) 01:56, 13 January 2014 (UTC)

In fact, you are right. However, you did use that interpretation, you took it there, as you did for benzene/cycloalkene. --Dirk Beetstra ^{T C} 04:44, 13 January 2014 (UTC)

(edit conflict)Multiple, for some yes (I would say if they involve different wikiprojects ..), but here we get sometimes 10 for one compound, all related to one project. Yes, that is damaging the process of improving these articles, someone who is a specialist in esters will not find the article now, because it is in the cycloalkene-stub-category, so the only solution is to add all possible functional groups to it at once (this is not a go-ahead to do that solution from now on!). Moreover, as I pointed out, some of those 10 are debatable - does it in the class of alkenes, dienes or α-β-unsaturated amides (the latter stub category would need upmerging as it likely will often not have enough members). And if you insist that benzene is a cycloalkene while following IUPAC ... then maybe it is time to stop you from everything chemical compound classification (which is including naming and categorisation) related. (after EC) Classification as EdChem suggests as an ester ignores all the other functional groups in the molecule, and it is not only the ester that gives it its properties, that one is just the one with the 'highest ranking' in the IUPAC naming system. --Dirk Beetstra ^{T C} 13:30, 11 January 2014 (UTC)

Just to clarify, Dirk, I am not advocating or suggesting categorising by IUPAC PFGs (though at least it would be systematic, unlike Plasmic's approach), I prefer the general organic stub classification without specifying one of several functionalities. I hope you would agree that 2-carbomethoxytropinone is not a cycloalkanethis was a typo, I meant cycloalkene, though. EdChem (talk) 13:43, 11 January 2014 (UTC)

I know you're not, EdChem - but just to point out that I would disagree with that approach as well. Eh, based on IUPAC, it is an cycloalkAne (the naming is based on the skeleton of a bicyclooctAne, specifically the bicyclo[3.2.1]octane, even a 8-aza-bicyclo[3.2.1]octane .. note that the IUPAC rules here do not classify this compound as an amine as you did suggest, this is an aza-alkane (sigh .. do we see where this and the IUPAC-related discussion about alkenes above is getting us!)!), not a cycloalkEne as Plasmic Physics seems to suggest. --Dirk Beetstra ^{T C} 13:50, 11 January 2014 (UTC)

Yes, it is a cycloalkane, it's a typo - I meant cycloalkene - which I have now corrected. EdChem (talk) 13:58, 11 January 2014 (UTC)

I have never added 10 stub templates to one article, you're using unrealistic hyperbolism to demonstrate your point. I'll clarify, I was told that multiple stub templates (within the same project) are perfectly acceptable. Moreover, we do not have stub templates for every functional group, so what you propose will occur, regarding that point, cannot be realized in the foreseeable future. I did not say that I was following IUPAC when classifying benzene as a cycloalkane, I noted above that for the sake of simplicity, I considered only the Kekule forms. Plasmic Physics (talk) 21:46, 11 January 2014 (UTC)

Well, you were on your way, you suggested the {{cycloalkene-stub}}. And this is not a hyperbole, this is a logical result - if you start this, then that is the end-result, it is actually what, for consistency sake, you should have done - make sure it is in ALL the stub categories, and as I argued, as long as it is not you are damaging Wikipedia (well, also when it is in all those stub categories). Also note that we do have stub templates for some functional groups already (even for the ones mentioned above) which you did not add - no, you singled out cycloalkene. And no, you are obvious not following IUPAC, or any other authority/convention for that matter, when you say that benzene is a cycloalkene (for the sake of simplicity, Communesin B is also an alkane, which brings the total number of stub-possibilities to 9, and I did not consider yet the enol forms that may exist in the compound ...). --Dirk Beetstra ^{T C} 04:32, 12 January 2014 (UTC)

Auto spell corrector keeps miscorrecting me - as I type 'cycloalkene', I'm corrected to 'cycloalkane'. To determine whether it is truly damaging or not, would require the more experienced opinions from admins participant to WikiProject stub sorting. I was taught that even though benzene is an aromatic compound, it is useful to consider it as a cyclotriene, in a similar way to Lewis diagrams versus MO diagrams. Plasmic Physics (talk) 01:56, 13 January 2014 (UTC)

• Out of interest, why do we use 2 different systems for organising stub articles? We overwhelmingly use the {{WikiProject Chemistry}} tag on talk pages to handle page ranking (and so we can track activity via toolserver). Using the categories system seems a little mad, {{Organic-compound-stub}} currently contains 1119 pages, I can't imagine anyone is going to search through all that trying to find something specific. Project Osprey (talk) 12:05, 11 January 2014 (UTC)

I don't think that people search the category, I hope they mainly stumble on the tag at the page, or at best pick a random stub from the category (which is another reason why I think that splitting it is damaging).

2 systems - I think we follow Wikipedia's general system for stub-tagging (and I think that that is important in the stub-stage of an article to be noted on the page itself), while afterward the talk-page tag is tracking further (it is only double in the stub-stage). --Dirk Beetstra ^{T C} 13:30, 11 January 2014 (UTC)

Sanctioning

• A WP:COMPETENCE-based sanction would seem long overdue. Andy Dingley (talk) 13:24, 11 January 2014 (UTC)

I support that proposal, reluctantly (because he wants to help). --Smokefoot (talk) 18:57, 11 January 2014 (UTC)

I am not aware of other incidents involving this user, but this incident is a clear demonstration of incompetence and an inability to work well with other editors. At the very least, why not use {{aromatic-compound-stub}}?Testem (talk) 11:05, 13 January 2014 (UTC)

On what grounds? Plasmic Physics (talk) 21:58, 11 January 2014 (UTC)

1. You don't appear to understand the difference between an aromatic compound and a cycloalkene.
2. You classified 2-carbomethoxytropinone as a cycloalkene, not as a mistake but as a deliberate choice which you have defended apparently without realising that keto-enol tautomers exist in equilibrium for every aldehyde and ketone with a protonated α-carbon.
3. More than a hundred incorrect and / or inappropriate recategorisations of stubs are at issue here, and you have yet to acknowledge that you might be wrong, although I acknowledge and appreciate that you have not continued with them.

Do you really not see why some fellow editors have doubts about your competence matching your enthusiasm? Did you consider asking for input about recategorising stubs, recognising that it might be controversial? EdChem (talk) 00:28, 12 January 2014 (UTC)

I understand perfectly well, the difference between 'aromatic' and 'cycloalkene'. I also knew about general keto-enol equilibria, what is wrong with that classification? Whether the recategorisations are incorrect and/or inappropriate is a matter of perspective. I could not possibly have foreseen your negative reaction. I did not consider it worthy of appealing to consensus for that reason, and in addition, I see stub categorisation as a trivial maintenance issue not concerning the general audience. Plasmic Physics (talk) 01:56, 13 January 2014 (UTC)

Perspective or otherwise, everyone here disagrees with you and your attitude surrounding the matter means that unnecessary extra time is being wasted dealing with it. Testem (talk) 11:05, 13 January 2014 (UTC)

See 1, 2--122.109.114.21 (talk) 02:56, 13 January 2014 (UTC)

"I understand perfectly well, the difference between 'aromatic' and 'cycloalkene'." Then you know that they are not the same, in fact. "Whether the recategorisations are incorrect and/or inappropriate is a matter of perspective." No, it's not subjective or questionable whether an aromatic is an alkene, both in fact and even in your own statement recognizing that. DMacks (talk) 02:30, 13 January 2014 (UTC)

Yes, I know they are not the same in every respect. The issue is not whether an aromatic is exactly an alkene, the issue is whether the Kekule form can be handled as a cycloalkene, as is done elsewhere outside of Wikipedia; and that is not the only issue that has been raised. Plasmic Physics (talk) 03:13, 13 January 2014 (UTC)

Where else are kekule forms considered as cycloalkenes? Testem (talk) 11:05, 13 January 2014 (UTC)

There is no such thing as a Kekule form. A Kekule structure (not a form) is an artifact in valence bond theory. It does not exist. It is quite different from the keto and enol forms of a ketone, which are chemical entities in equilibrium. An aromatic compound is not an alkene in any respect. I suggest that you leave stub sorting of chemicals to someone who understands chemistry. --Bduke (Discussion) 04:06, 13 January 2014 (UTC)

Whether or not benzene is a cycloalkene, the logical extension of what Plasmic Physics suggests is that this compound, at the least, should be in {{aromatic-compound-stub}} (where Plasmic Physics did not put it, but I hope that Plasmic Physics understands that it should be), and in, as Plasmic Physics suggests, in {{cycloalkene-stub}} (whether or not correctly). So Plasmic Physics suggests, plainly, that a chemical compound stub should be categorised in ALL applicable stub groups for each single functional group (and even, implied functional groups - a ketone with an &alpha-CH hence is besides a {{ketone-stub}}, also an {{alkene-stub}} and an {{alcohol-stub}}. And that is what Plasmic Physics does not seem to have consensus for. --Dirk Beetstra ^{T C} 04:44, 13 January 2014 (UTC)

Hey now, that is your plain suggestion to spam articles with every applicable stub template. Plasmic Physics (talk) 23:28, 14 January 2014 (UTC)

No, that is what I suggest that should not be done. --Dirk Beetstra ^{T C} 03:51, 15 January 2014 (UTC)

Then we agree? Plasmic Physics (talk) 10:11, 16 January 2014 (UTC)

Agree, on what? That we should only put selected stub-templates for cases which surpass the 60 article limit? No, we do not agree on that either, obviously. --Dirk Beetstra ^{T C} 10:25, 16 January 2014 (UTC)

By "Kekule form", I am referring to the structural formula. I know that it does not exist, that is what I explained above when comparing Lewis diagrams with MO diagrams. Although, MO diagrams themselves do not represent reality exactly either. I also know that it is different from chemical equilibria, though I can't see how you made that connection. Plasmic Physics (talk) 23:28, 14 January 2014 (UTC)

Raak wys. 122.109.114.21 (talk) 00:41, 15 January 2014 (UTC)

What are implying? Being 'smart' never afforded anyone anything good. Plasmic Physics (talk) 10:11, 16 January 2014 (UTC)

The problem is that I disagree with the split of the main stub-category over what in the end may very well be hundreds of categories for a mere 1200 pages, where certain pages, if it is carried to its logical end, carry over 10 different stub categories for each of the individual functional groups. That is what I vehemently oppose (even if the stub-sorting WikiProject suggests that it is fine to have more than one stub-category relating to one WikiProject per stub). --Dirk Beetstra ^{T C} 04:44, 13 January 2014 (UTC)

That can't happen, as there is a requirement for new stub categories, of a minimum of 60 candidates. It was the Chemistry Project that made the suggestion to which you refer. Plasmic Physics (talk) 23:28, 14 January 2014 (UTC)

Exactly. So we end up with 'you're an alkene stub, but I am sorry, even though you are an ester stub, there are less than 60 esters so we are not going to call you an ester stub, and I don't care if that confuses the hell out of our editors (and possibly readers). It is that wonderful problem with WP:SMALLCAT - one can devise a perfectly consistent 'larger scheme' of categories, where each final category has exactly one item in it (and unlikely to grow much beyond that). And you can't delete those small categories, because they are part of the larger scheme. But is it helpful to have things so fine grained? No. WP:SMALLCAT should read that the larger scheme should, on average, have a reasonable number of members, otherwise the larger scheme is invalid. But that is another rant.

I wonder, if you fish out all the aromatic compounds and others which you tagged whether you end up with 60 cycloalkenes anyway.

Can you point me to that suggestion? I wonder about the context of it. --Dirk Beetstra ^{T C} 03:51, 15 January 2014 (UTC)

Finding the suggestion can't easily be done, it is on one of the hundreds of stub articles' talk pages. Plasmic Physics (talk) 10:11, 16 January 2014 (UTC)

'.. [O]n one of the hundreds of stub articles' talk pages'? I though this was discussed on the stub sorting wikiproject talk page. This is a very local 'consensus' (if any, I still need to see it in its context). --Dirk Beetstra ^{T C} 10:25, 16 January 2014 (UTC)

4-Methylcyclohexanemethanol

Interesting factoid - this article was visited >4300x yesterday. A lot of it was spilled in a U.S. river earlier this week, and this spill has basically shut down the water supplies for tens of thousands of people. From the chemistry perspective, I still cannot imagine why any company would make this stuff intentionally. Maybe its just a cheaply available side product. Fortunately, the compound is probably pretty benign as things go - not that I want it in my drinking water.--Smokefoot (talk) 18:57, 11 January 2014 (UTC)

21000 hits yesterday. We're still looking for detailed info on water solubility, which is of importance in solving this spill. The other main problem is that the spill was probably not pure compound but a mix.--Smokefoot (talk) 16:27, 12 January 2014 (UTC)

Can't find a thing. I'll try scifinder in the morning. BTW, here are the CAS No's for cis isomer (3937-48-2) and trans isomer (3937-49-3). I've checked them out too, but there's virtually no data on their properties either. Project Osprey (talk) 18:02, 12 January 2014 (UTC)

Scifinder also pulls a blank, although it does give a predicted value of 7.7 g/L. I've added some refs for other properties but they're kind of old, revert if you're unhappy with them. Project Osprey (talk) 10:15, 13 January 2014 (UTC)

I just wanted to note that using predicted chemical properties is generally not a good idea (I realize they haven't been added to the article in this case, but they have been added to other articles.) Most algorithms for making these predictions are notoriously inconsistent in their correlation with experimental data, and different ways of making these predictions rarely agree with each other. -- Ed (Edgar181) 23:57, 16 January 2014 (UTC)

Proposal to split octanol

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.122.111.244.144 (talk) 05:46, 17 January 2014 (UTC)

And how is this remark helpful, dear 122.111.244.144. 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? 122.111.244.144 (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? 122.111.244.144 (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. 122.111.244.144 (talk) 01:20, 18 January 2014 (UTC)

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

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)

Article-title of a "name" reaction

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)

Image issues in captodative effect

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 and Genger14:), the course-related editors (@ChemLibrarian and 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)

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

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)

AfC submission

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)

Wikipedia talk:Articles for creation/flow miniplant

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)

Complex

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)

New article, potential conflict of interest

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)

Merge proposal: Organofluorine compound into Organofluorine chemistry

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

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

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

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. -- 70.24.244.161 (talk) 19:54, 9 February 2014 (UTC)

Ferrocyanide

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

AfC submission

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)

Bergius process question

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?

118.209.161.155 (talk) 19:01, 13 February 2014 (UTC)Keith

Low field NMR merger

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

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

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)

AfC submission

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

Help a new user on an article

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)

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

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:

• Notes and Records: the Royal Society journal of the history of science
• Biographical Memoirs of the Fellows of the Royal Society

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)

Improved_temperature_options_in_Chembox

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

Most active WikiProject Chemistry members

Dear WikiProject Chemistry,

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

Tribromosilane

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)

Adding meso isomers to isomerism image

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)

Terminology

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

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

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)

Article: Carbonite (ion)

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-CO₂⁻still

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.

Reasons:

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)

Silicon and hydrofluoric acid

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

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 !!!

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:

• Notes and Records: the Royal Society journal of the history of science
• Biographical Memoirs of the Fellows of the Royal Society

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)

Royal Society of Chemistry Event

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 https://wiki.wikimedia.org.uk/wiki/Royal_Society_of_Chemistry_2014_Event 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)

AfC submission - 17/03

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)

• Wikipedia talk:Articles for creation/Surface Hopping. FoCuSandLeArN (talk) 18:45, 18 March 2014 (UTC)

AfC submission - 24/03

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

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)

IUPAC vs Common Usage

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)

Wikipedia talk:Articles for creation/Aegis

Dear chemistry experts: Is this a notable chemistry topic? Should the Afc submisssion be kept and improved, or deleted as a stale draft? —Anne Delong (talk) 03:21, 20 April 2014 (UTC)

Invitation to User Study

Would you be interested in participating in a user study? We are a team at University of Washington studying methods for finding collaborators within a Wikipedia community. We are looking for volunteers to evaluate a new visualization tool. All you need to do is to prepare for your laptop/desktop, web camera, and speaker for video communication with Google Hangout. We will provide you with a Amazon gift card in appreciation of your time and participation. For more information about this study, please visit our wiki page (http://meta.wikimedia.org/wiki/Research:Finding_a_Collaborator). If you would like to participate in our user study, please send me a message at Wkmaster (talk) 17:31, 25 April 2014 (UTC).

Invitation to User Study

Please refer to the previous message. Thank you. Wkmaster (talk) 17:39, 25 April 2014 (UTC)

Royal Society journals - subscription offer for one year

I'm delighted to say that the Royal Society, the UK’s National Academy for science, is offering 24 Wikipedians free access for one year to its prestigious range of scientific journals. Please note that much of the content of these journals is already freely available online, the details varying slightly between the journals – see the Royal Society Publishing webpages. For the purposes of this offer the Royal Society's journals are divided into 3 groups: Biological sciences, Physical sciences and history of science. For full details and signing-up, please see the applications page. Initial applications will close on 25 May 2014, but later applications will go on the waiting list. Wiki at Royal Society John (talk) 03:02, 29 April 2014 (UTC)

Fischer Indole Synthesis

I am writing this to inform you about an error regarding the Buchwald Modification to the Fischer indole synthesis. The initial hydrazone cross coupling occurs between benzophenone hydrazone and an aryl bromide, not the correspondig enolizable hydrazone. The installation of the latter hydrazone occurs as a result of hydrolysis of the benzophenone hydrazone followed by the condensation of the enolizable ketone to ultimately cyclize to form the desired indole. In this way, benzophenone acts as a protecting group for the isolation and handling of the cross coupled intermediate.

Thanks,

Chris Gabriel University of California, Santa Barbara — Preceding unsigned comment added by ChrisMGabriel (talk • contribs) 13:38, 4 May 2014 (UTC)

Wikipedia talk:Articles for creation/Salt-water batteries

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)

DMacks and 0x0077BE, is there any useful content in the draft that should be moved to one or the other of these articles? —Anne Delong (talk) 01:24, 20 April 2014 (UTC)

I don't think there's anything salvageable, and the specific title seems an unlikely search-phrase. The only novel claim is the "Water Salinity Difference" item in the "Future of Salt-Water Batteries" section, but it's fairly preliminary primary research (interesting and novel, but doesn't yet appear to be noticed by other reliable sources). DMacks (talk) 17:51, 25 April 2014 (UTC)

i'm not sure where to start on how confused it is 24.3.8.179 (talk) 03:05, 25 April 2014 (UTC)

I agree. There is a lot of weird stuff there, as well as some kernel of topic already covered elsewhere. DMacks (talk) 17:57, 25 April 2014 (UTC)

Okay, it has faded away... —Anne Delong (talk) 01:46, 12 May 2014 (UTC)

Other names as redirects

Is there a way that "other names" in the Chemboxes could automatically be made into redirects to the same topic? --Smokefoot (talk) 16:20, 19 April 2014 (UTC)

I don't understand this. Could you give a specific example or two? DMacks (talk) 16:43, 30 April 2014 (UTC)

Well in the Chembox, there is typically a list of other names for a compound. Like here:

Lithopone

Names
Other names Barium zinc sulfate sulfide, Enamel White, Pigment white 5, CI Pigment white 5, Barium zinc sulfate, Barium zinc sulfide, Lithopone B301, ZNS 28-30%, Lithopone 28-30%, LithoponeB311, Zinc sulfide, Barium sulfate Mixture, Pigment White 5 (77115), Becton White, Charlton White, Zincolith
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It would be very nice if "Becton White" automatically became a redirect to "lithopone" by virtue of being in the "other names" section. Does this make sense? --Smokefoot (talk) 17:10, 30 April 2014 (UTC)

So when someone added "Becton White" to that list, Becton White→Lithopone would be automatically created? Interesting! If it's listed, then searching should already find it (as text) even without having an actual article (-redirect) at that name. But it would help for other articles that have links to the alt names. Seems a little ripe for abuse IMO (might want to have a delay to allow antivandals to revert any bad entries). And many of the entries in the example here don't seem like worthwhile links (different concentrations, or adjectives added to chemical names). Maybe a bot could collect them and list the non-existing ones for manual triage? DMacks (talk) 17:21, 30 April 2014 (UTC)

It will never be automatically, like fixing double redirects (automatically) is turned of. But the template could check if the page exist. Christian75 (talk) 08:08, 22 May 2014 (UTC)

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Adikhajuria (talk) 11:33, 25 May 2014 (UTC)

Extraction of carbon dioxide from seawater

Dear chemistry experts: After watching this video I looked to see what Wikipedia had to say on this topic, and couldn't find anything. There are plenty of news, journal, and other reports about this (THESE, for example). Is there already information somewhere on Wikipedia about this topic, and, if not, would it be appropriate to start an article about it? —Anne Delong (talk) 14:38, 12 May 2014 (UTC)

Have a look at Carbon dioxide removal, and Carbon sequestration. I suggest adding to one of those articles. Plasmic Physics (talk) 23:23, 12 May 2014 (UTC)

Those articles are concerned with long term storage of carbon as a method of mitigating climate change. The topic I am suggesting is the opposite; retrieving it as a first step in the on-site creation of synthetic fuel. Examples could be providing fuel on a remote island, or synthesizing fuel on an aircraft carrier. —Anne Delong (talk) 10:15, 13 May 2014 (UTC)

In that case, try Synthetic fuel. See this link, it is not about fuel from seawater, but it is related. Plasmic Physics (talk) 11:56, 13 May 2014 (UTC)

• Bit complex this. For the most part CO₂ exists in seawater as a range of dissolved carbonates. The partial electrolysis of water gives H₂ and H⁺ (and some O₂ no doubt). The H⁺ liberates the CO₂ and I'm guessing that goes into a reverse water gas shift to give you some CO. CO and H₂ then feed into a Fischer–Tropsch process to produce fuel. None of these steps is novel but joining them all together without the result being hugely inefficient is quite an achievement. Project Osprey (talk) 20:26, 14 May 2014 (UTC)

• I agree, and this is what caught my interest, since the references seem to indicate that this could be done at a cost that was not too prohibitive. I thought someone at this project might like to write it up. Dim memories of my high school chemistry classes in the '60's have left me unprepared to do it myself. —Anne Delong (talk) 04:00, 25 May 2014 (UTC)

Will also look into it Anne. Good to "see" you as always. Le Prof Leprof 7272 (talk) 06:12, 1 June 2014 (UTC)

Nondescript name vis-a-vis steeochemistry, yet stereodefined structures in box, etc.

General and specific questions here—how to fix the morass of conflicting information about compound identity and structure at this site, [1]. Expert replies requested (knowledgeable about clear stereo/structure issues, but also about Wiki standards for stereo-nondescript names, and structures that should appear). Le Prof Leprof 7272 (talk) 02:46, 2 June 2014 (UTC)

Opening discussion on future course of Natural Product article, [2]

PLEASE SEE THIS LINK [3], REGARDING AN ATTEMPT TO RESTART PRODUCTIVE WORK ON THE "NATURAL PRODUCT" [4] ARTICLE. THANK YOU. LE PROF. Leprof 7272 (talk) 07:41, 2 June 2014 (UTC)

Wrong category name?

Please express your opinion here. --Daniele Pugliesi (talk) 02:23, 9 June 2014 (UTC)

Wikipedia talk:Articles for creation/Indium-mediated allylations

Hello, chemists - one more of those abandoned AfC submissions. Is this a notable chemistry topic? Should the page be kept and improved instead of being deleted as a stale draft? —Anne Delong (talk) 14:05, 8 June 2014 (UTC)

• already published as Indium-mediated allylation V8rik (talk) 20:12, 8 June 2014 (UTC)

• Thanks for finding that. Since both were written by the same single author, the draft wasn't needed, so I have deleted it. —Anne Delong (talk) 04:22, 11 June 2014 (UTC)

AfC submission - 10/06

Draft:Chemistry of Adhesive Tapes. FoCuSandLeArN (talk) 00:42, 11 June 2014 (UTC) There is NO "chemistry of adhesive tapes". There is chemistry of adhesives. And there is the fabrication of adhesive tapes, sort of an engineering thing. Otherwise we are going to get a whole series of articles on "Chemistry of [your topic here]. The article should have been integrated into adhesive tape and pressure-sensitive adhesives. Anne, can you induce those blendings, because the two enhanced articles would be stronger than these three self-standing things. A problem (and a strength, in some cases) with Wikipedia is that anyone can create an article, it is more challenging to integrate. --Smokefoot (talk) 12:06, 12 June 2014 (UTC)

Schoolwork review needed

A class project has recently added a lot of content to preservative. I have found it to be riddled with errors and biases. I have started cleaning up and correcting some of it, but if other chemists could take a look at it, that would be helpful. ChemNerd (talk) 11:39, 14 June 2014 (UTC)

Fluorescein atropisomerism ?

question with no respons on fr:Discussion_Projet:Chimie#atropoisomérie_de_la_fluorescéine_?
I see this image with mark of atropisomerism on Fluorescein isothiocyanate and I found only this abstract which seems to proove the fluorescein atropisomerism. I search for other refs to put a section stereochemistry on the articles like Fluorescein and derivated (eosins, rhodamines, etc.) but for the moment I don't find anyone= HELP ! --Titou (talk) 12:14, 3 June 2014 (UTC)

Its been used for fluorescence anisotropy binding studies - so yes, it must have restricted rotation. That's quite a complex example though, I'll see if I can find something a bit more general.Project Osprey (talk) 13:40, 3 June 2014 (UTC)

• Actually, strike that, this is more complex than it first looked... it has restricted rotation, but not atropisomerism. The benzene can't rotate, but that doesn't matter because the hydroxy-xanthenone can rapidly tautomerise. It also seems to have a lactone form (cas: 3326-32-7), I've added an image of the corresponding fluorescein to give you an idea, but I can't find an authoritative source on how easy it is to switch between isomers. Project Osprey (talk) 15:42, 3 June 2014 (UTC)

Various conditions make certain fluoresceins more or less stable one way or another (substituents on the rings, intramolecular H-bonding, etc.), and altering the conditions can trigger a switch. See for example: doi:10.1039/C1OB05387F, PMID 17471452, doi:10.1021/ja01404a016, doi:10.1016/S0927-7757(99)00313-1. I don't know the kinetics of the switch, or especially whether there is rapid equilibrium with just a possibly strongly favored direction vs a fairly stable state that can be caused to make a non-reversing/one-way-reaction change to the other. DMacks (talk) 17:55, 3 June 2014 (UTC)

Okay. So it's may be only the Fluorescein isothiocyanate which have atropoisomer like the molecule in the abstract? or we must modify the picture which would be wrong --Titou (talk) 13:02, 6 June 2014 (UTC)

I think that all of these fluroecein derivatives can show atropisomerism if they have the lactone that can be opened by keto-enol tautomerism as it is the ring-opened forms that are atropisomers. --The chemistds (talk) 13:09, 6 June 2014 (UTC)

All good discussion, but someone might mention to the posting editor, @Titou, that none of this matters to WP if a good secondary source on the matter cannot be found. The ACS abstract presented in no way can be considered a suitable source to make such a claim here. Or have I missed a link-out to a good source, here? (There is evidence that Applied Biosystems had IP in this, beginning in the early 2000s, likely through acquisition, but I have no wish to fuel a conversation that cannot come to productive fruition.) Bottom line, not even the beginnings of a "proove" here — simply not ready for prime time. Cheers. Le Prof Leprof 7272 (talk) 05:54, 9 June 2014 (UTC)

Okay, then corrects, please, this picture since the mark of atropoisomerism have no source and it seems out of question to discuss if there isn't good secondary sources ! --Titou (talk) 13:11, 15 June 2014 (UTC)

Alkylimino-de-oxo-bisubstitution

The article alkylimino-de-oxo-bisubstitution was originated by a respected editor, but this title is IMHO just too awkward. Many of us have lots of experience with imines and Schiff bases, but, I have never ever heard of the mouthful alkylimino-de-oxo-bisubstitution. Almost sounds like a joke. So I am wondering if this material might be better blended into imine. Since there is occasionally resistance to mergers, alternative ideas are welcome. BTW, if anyone knows the difference between "imine" and "Schiff base", please leave a note here! --Smokefoot (talk) 16:20, 19 April 2014 (UTC)

I could support merging to imine (and/or hemiaminal). It might be the technically correct name based on systematic rules for the reversible N/O substitution, but I don't think there's sufficient content specific to this reaction or notability of it itself, rather only in its application to carbonyl/hemiaminal/imine interconversions. The content in the article beyond the mechanism is interesting (the geometry of the aziridine, the color-changing upon thiol cyclization), but seems cherry-picked. OTOH, that latter one could go into the imine article, as there are no S-attack reactions in the "reactions of" section, and maybe also as an Baldwin's rules example. DMacks (talk) 04:20, 29 April 2014 (UTC)

for once I agree with IUPAC , the name originates with them and was then adopted by March and that is how I learned of it. A Joke? Poor Jerry March. Every organic chemistry textbook has this reaction type so notability ensured. Why not an alternative name. Organic Mechanisms: Reactions, Methodology, and Biological Applications / Xiaoping Sun suggests "nucleophilic addition of amines to ketones and aldehydes". A lot of pages exist in wikipedia with a name like that. Further: we have a lot of pages on functional groups and we have a lot of chemical reaction pages that link between them. it makes sense to keep it that way. The aziridine case seems relevant. The scope example is exactly what it is: an example. Details can be demoted to notes. I do not understand the cherry picking comment. V8rik (talk) 19:37, 17 June 2014 (UTC)

We are involved in an experimental science: walk down your hallway and ask your friendly organic chemist to name or describe the condensation of an amine and a carbonyl to give an imine. Seems pretty unlikely that you'll this response "Oh, you mean the alkylimino-de-oxo-bisubstitution!" For that reason, it seemed reasonable to contemplate putting this content into an article that would come up in searches. As a service to readers vs obedience to IUPAC. So my thought is nothing to do with owning an article or anti- or pro merger thoughts, it is solely about helping readers who want info on imine condensations. We run this reaction often, and I have yet to hear this term. But maybe I need to ask around. Not a big deal. --Smokefoot (talk) 23:10, 17 June 2014 (UTC)

• let me restate my enthusiastic support for a name change. I have already made one suggestion. Anyone else? V8rik (talk) 15:31, 18 June 2014 (UTC)