Wikipedia talk:WikiProject Chemicals/Archive 2014

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2-Carbomethoxytropinone

This article is currently at AFD: Wikipedia:Articles for deletion/2-Carbomethoxytropinone. If anyone would like to help out, the article and the AFD would benefit from the attention of additional chemists. -- Ed (Edgar181) 13:05, 2 January 2014 (UTC)

Nomenclature-based renaming

See Talk:NBOH-2C-CN where several articles are requested to be renamed using a different nomenclature -- 70.50.148.122 (talk) 03:34, 18 January 2014 (UTC)

Is an amalgam an alloy?

Amalgam (chemistry) defines itself as a "substance formed by the reaction of mercury with another metal" (links omitted, italics mine). It never says it is an alloy, but that term is used in one of the later sections and the alloy article gives amalgams as an example. There are scattered questions over years on the talkpage asking several related questions, getting at the concern that the article never really discusses the nature of this "reaction" or its resulting "substance". How is it other than just an alloy where one of the components is specifically mercury? DMacks (talk) 16:01, 24 January 2014 (UTC)

Greenwood and Earnshaw refers to amalgams as alloys. IUPAC does not define the term. Not that I know of any other alloy with NH₄⁺. BTW, the article suggests Hg-H bonds for the ammonium derivatives, which seems unlikely. There must be a book on amalgams, but searching turns up a lot of things on dentistry. --Smokefoot (talk) 23:44, 24 January 2014 (UTC)

FA articles not in the CHEM AQ overview?

I do not understand why not all qualities are in the quality overview. E.g. Category:FA-Class chemicals articles. -DePiep (talk) 15:10, 26 December 2013 (UTC)

It is something to do with Template:WikiProject Chemicals but I can't figure it out. Graeme Bartlett (talk) 10:31, 25 January 2014 (UTC)

Ammonium phosphate

This is rated as high importance but is a stub because the salt (NH₄)₃PO₄ is unstable. I suspect the importance stems from the use of ammonium phosphates in agriculure, but the fertilizer ammonium phosphates are diammonium phosphate and monoammonium phosphate which are both rated as low importance, the former is a "stub" and the latter a "start". There is also an ammonium phosphate (compounds) index page. Could we possibly change the importance rating on these compounds?Axiosaurus (talk) 14:05, 27 January 2014 (UTC)

I have changed it to low. I think you could have just gone in and changed it yourself rather than seeking a consensus. Perhaps we need more explicit rules on what is high, or medium importance, and a consensus for each article with "top". Graeme Bartlett (talk) 20:55, 27 January 2014 (UTC)

Also I changed MAP and DAP to mid. I think that any chemicals manufactured and sold in large quantities should be at least mid (if not high) importance. What do others think? Graeme Bartlett (talk) 21:03, 27 January 2014 (UTC)

The chemicals work list has stood the test of time quite well. I think any changes require a concensus, or at least flagging up to the wider community. Factors like commercial significance are part of the story but whilst some inorganics are significant in that regard, thousands or even millions of tons pa. , some are almost unknown to the general public. Axiosaurus (talk) 17:29, 28 January 2014 (UTC)

This thing on "(NH₄)₃PO₄ was sort of a chemical myth, so I converted an article that boasted of its import into one admitting that it is fragile and basically unimportant. In any case articles on "big boring salts" (BBS) often need attention. These BBSs include the alkali, alkaline earth, iron, and ammonium salts of sulfates, phosphates, nitrates, carbonates, hydroxides. These articles tend to collect all kinds of esoterica ("grandma's cleaning agent" type thing), which is not evil, but needs to be kept in check and described with some perspective. Petergans raised the point that many of these articles need some crystallography. I have tried to mention all of the hydrates for each of these materials. --Smokefoot (talk) 06:33, 28 January 2014 (UTC)

I am supporting what happened to ammonium phosphate. However Isn't the worklist historical? Some things out of scope do not make sense as they are major and important chemicals. But perhaps everything on that list should have importance at least mid. The worklist does not talk about importance ratings. The worklist only has 50 commodity chemicals, I think we can move on from that now! Graeme Bartlett (talk) 20:44, 29 January 2014 (UTC)

Resveratrol article

Like I stated at Wikipedia:WikiProject Pharmacology, "More eyes on the Resveratrol (edit | talk | history | protect | delete | links | watch | logs | views) article are needed. New editor Local4554 is repeatedly blanking material at the article without justifying his edits, and despite warnings not to do so." Flyer22 (talk) 18:47, 12 February 2014 (UTC)

Stereochemistry of norbornene derivatives

I noticed that the stereochemistry of chlorinated norbornene is opposed. In the case of chlordane, dieldrin, endosulfan and heptachlor the substituent is “upwards” exo,

• File:Chlordane-3D-balls.png
• 
• 
• File:Heptachlor 3D.png

whereas for aldrin and endrin the substituent is “downwards” endo.

• 
• 

• Is this correct? Or are they always a mixture of both isomers?
  
• A related question concerning dechlorane plus: For the syn and the anti isomer, there are two possibilities each, i.e. “upwards” exo and “downwards” endo. Is only one occurring in the technical product?

--Leyo 23:41, 15 February 2014 (UTC)

In general, it depends on the particular reagents involved whether you get the endo or exo isomer: http://www.chemtube3d.com/Diels-Alder%20-%20Endo%20and%20Exo.html. To summarise Clayden et al, the endo isomer is the kinetic product and is obtained if the particular Diels-Alder reaction in question is irreversible (e.g. cyclopentadiene + maleic anhydride). The exo isomer is the thermodynamic product, so is obtained if the reaction is reversible (e.g. furan + maleic anhydride).

Of all the images presented above, only the aldrin one is based on a crystal structure. I'll see if I can find structural data for the others. --Ben (talk) 11:14, 16 February 2014 (UTC)

I've found the crystal structures of all of these molecules and all except aldrin are currently drawn as the (wrong) exo isomer. I'll make new images if I have time today. --Ben (talk) 13:55, 16 February 2014 (UTC)

Thanks a lot for your investigations! It is great to get them corrected since they have been used quite a number of times (incl. outside of Wikipedia).

Did you look for crystal structures for dechlorane plus, too? If File:Dechlorane plus syn isomer.svg turned out to be incorrect, I will correct it. --Leyo 17:34, 16 February 2014 (UTC)

No probs. Haven't had a look for dechlorane plus yet, but will do tomorrow. Cheers. --Ben (talk) 18:39, 16 February 2014 (UTC)

Thank you for uploading the corrected ball-and-stick models. What do we best do with the old ones? Clearly stating in the description pages that the depicted isomer is not the one that is (primarily) synthesized? Or even deleting these images?

In the case of endosulfan, chlordane and heptachlor, the skeletal structure needs to be corrected, too. For the latter two, also the position of the chlorine atoms in the five-membered ring is opposite. Shouldn't the same isomer be shown in both types (skeletal, ball-and-stick), even though they are mixtures of isomers? Endosulfan, on the other hand, is a mixture of two conformational isomers arising from the pyramidal stereochemistry of sulfur. Should we also add a note into the chembox stating that the substances are mixtures of isomers? --Leyo 20:17, 16 February 2014 (UTC)

If the commercially available, widely-used form of the pesticide genuinely contains a mixture of isomers, we should probably discuss this in detail in a section on structure and composition, and the skeletal formula and 3D models should be presented there rather than in the chembox. For others, where the images truly represent what's in the bottle, the chembox is the best place for them. I agree the skeletal formulae should be redrawn.

I found two crystal structures for dechlorane plus, reported in Tetrahedron Lett. (1991) 32, 3289-3292. --Ben (talk) 10:48, 17 February 2014 (UTC)

Thank you. I drew a skeletal formula of the anti isomer based on this paper and added it to the article.

Concerning the other issue, more opinions would be beneficial. --Leyo 22:59, 17 February 2014 (UTC)

Wikipedia talk:Articles for creation/Barium Metaphosphate

Hello, chemists! Is this a notable chemical, and should this old stale draft be kept? —Anne Delong (talk) 18:11, 17 February 2014 (UTC)

I have moved it to an article, but it needs work. Graeme Bartlett (talk) 21:10, 20 February 2014 (UTC)

I fixed some spelling and grammar, but the text needs clarification from someone with more knowledge of chemistry. —Anne Delong (talk) 04:04, 21 February 2014 (UTC)

Calcium_citrate#Chemical_properties

The paragraph about taste reads 1.) like a 5th-grader essay, and 2.) it's bull... I have some calcium citrate tetrahydrate right here, pure and properly labeled from a pharmaceutical manufacturer. It's chalky and tastes of not much anything, and that's a fact.

An unpublished fact, unfortunately, as far as my web searches are going. Should I delete the whole part anyway and replace it with my "original research"? Heck I would mistrust such an edit even myself. Can someone from this project help out? 217.231.102.73 (talk) 14:06, 20 February 2014 (UTC)

I removed the paragraph. Graeme Bartlett (talk) 11:12, 21 February 2014 (UTC)

Help needed: Urethane

Greetings! Expert help is needed to fix the last batch of incoming links to the disambiguation page, Urethane. Any help would be much appreciated! bd2412 T 22:21, 24 February 2014 (UTC)

 Done EdChem (talk) 22:39, 24 February 2014 (UTC)

Thanks! bd2412 T 00:09, 25 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 held by the Royal Society and the Royal Academy of Engineering, and 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#Temperatures_in_chembox:_more_improvements. -DePiep (talk) 00:23, 5 March 2014 (UTC)

Requested move: 2C-O

An editor has proposed that 2C-O be renamed to TMPEA, using the requested moves process.

The discussion is at Talk:2C-O#Requested_move, where input from members of this project would be very helpful. --BrownHairedGirl (talk) • (contribs) 10:18, 4 March 2014 (UTC)

Similarly, input would be appreciated at Talk:2C-E-NBOMe. Is there a suitable naming convention for these articles? Dekimasuよ! 23:44, 11 March 2014 (UTC)

Chemical structure of 102648-38-4

Has anyone access to the structure with the above CAS number? This seems to be bufagin according to several (commercial) websites. Thanks --ἀνυπόδητος (talk) 09:28, 16 March 2014 (UTC)

Chemspider shows the the following there appear to be 9 stereoisomers, several of which have unique names. Project Osprey (talk) 11:28, 16 March 2014 (UTC)

I've already found that entry, but (1) the CAS no. doesn't match, (2) "bufagin" is given only as a non-validated synonym of marinobufagin = marinobufagenin [marCinobufagin seems to be a typo], (3) there are only 32 H's as compared to 34 in http://www.chemicalbook.com/ProdSupplierGNCB71268697_EN.htm. Of course, ChemicalBook could be wrong.

The other stereochemistries are just variants with more or fewer stereocentres, with the exception of 23223509 which has the epoxy in α position. --ἀνυπόδητος (talk) 15:03, 16 March 2014 (UTC)

Template up for deletion

A template used on articles about chemicals, {{Drug-emerging}}, has been nominated for deletion at Wikipedia:Templates_for_discussion/Log/2014_April_10#Template:Drug-emerging. Please feel free to contribute to the discussion. -- Ed (Edgar181) 11:54, 10 April 2014 (UTC)

Two articles needing attention

The following two articles need attention:

• Polychlorinated biphenyl: major editwar by two new users
• Benzisothiazolinone: addition based on potentially low quality references

--Leyo 22:04, 8 April 2014 (UTC)

I warned the two new users at Polychlorinated biphenyl and reverted the recent additions to Benzisothiazolinone because they were copyright violations. -- Ed (Edgar181) 12:04, 10 April 2014 (UTC)

Apparently the edit warring at Polychlorinated biphenyl is related to ongoing litigation (see Wikipedia:Administrators'_noticeboard/Incidents#Participants_in_litigation_edit_warring) so a few chemists keeping an eye on that article and/or checking its current content would probably be a good idea. -- Ed (Edgar181) 12:02, 11 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) 07:53, 16 April 2014 (UTC).

"Data page" subpages

Is there a reason that this project uses statistics-only subpages in the form subject name (data page)? I noticed this when encountering Trichlorofluoromethane (data page) during new page patrol, and I then saw that there are some 150 similar pages.

Most of these seem to be perfect for inclusion in their main page, neither the main article nor the subpage are too long (e.g. in this case Trichlorofluoromethane wouldn't have a problem with the expansion that this "data page" would produce, the same applies to e.g. Dichlorodifluoromethane (data page) or a revised form of Fucitol (data page)). This would improve the main pages, decrease the number of unnecessary pages (it isn't really user-friendly to spread the info across multiple pages), and better match what other projects do and what the general policies indicate (e.g. WP:NOT opposes pages which consist only of statistics and the like). A page like Fucitol (data page) is really not what a Wikipedia article should look like, and I see no problem that is solved by making these separate page. By the way, Pyrene (data page) has been vandalized (or made more correct, whatever) since March 2009, i.e. 5 years ago: [1]. Fram (talk) 10:03, 1 April 2014 (UTC)

That would mean inclusion in the chembox infobox then? Interestingly, I was thinking to propose to make such data pages for the elements (which don't have the {chembox} at all). -DePiep (talk) 10:16, 1 April 2014 (UTC)

Moving this info in the mainpage might result in a form of 'table creep' - there is so much info about certain compounds which is informative, verifiable, encyclopedic, but presenting it all on the page itself may flood the page with data (most of it is just that, data) and make it 'unreadable'. Some of the data is 'discussable' (e.g. a melting point, which determines whether it is a liquid or a solid at room temperature (it is an 'observable property'), and that should be in the mainpage), other data is just data (the IR absorption frequencies do not determine a lot of the observable properties (still they do determine some properties - for water it determines why your kitchen microwave does what it does), and hence is put in the data page). The elements have all data moved into a template (making it difficult to edit for new editors, though it does not need to be edited generally either), one could consider here something similar with a collapsed template at the bottom in stead of a separate data page. --Dirk Beetstra ^{T C} 11:10, 1 April 2014 (UTC)

Collapsible box seems like a good solution. Fram (talk) 11:39, 1 April 2014 (UTC)

The elements have all data moved into a template is irrelevant. The question is the same were the {{infobox element}} present and filled in article page (code). -DePiep (talk) 12:08, 1 April 2014 (UTC)

The data pages were started years ago by consensus (I can't find the discussion in the archives, but only looked briefly) because some articles had accumulated too much data that was considered trivial. So instead of simply deleting it, and losing the data, it was moved to subpages. Personally, I don't have a preference for subpages vs collapsible boxes. But if the data is going to be moved back to the main articles in collapsible boxes, the {{chembox}} template will have to be modified, I think, because it currently automatically creates links to the data pages through a "Supplementary data page" link. Finally, I deleted Pyrene (data page) because it contained only an empty table. -- Ed (Edgar181) 12:12, 1 April 2014 (UTC)

Pages where the main purpose is to remove trivial info away from another article are generally frowned upon. If the info is trivial, then it shouldn't have its own page, but should be trimmed. You are right that moving this may eventually require a change to the template, although it looks to me as if the link is only shown when a (adatapage) exists, so getting rid of the separate pages doesn't leave redlinks in the template. Fram (talk) 12:38, 1 April 2014 (UTC)

A foldable footer box seems appropriate. There my be data repetition with the chembox. In the age when the separate data page was decided, I guess page size was more limited. (btw, {chembox} doesn't need change: once the data page is deleted/does not exist, no link is shown e.g., Pyrene). -DePiep (talk) 12:44, 1 April 2014 (UTC)

Know two or three data pages that make a good example to start with? -DePiep (talk) 14:03, 1 April 2014 (UTC)

To move back to the main article, in a collapsible box if too long or trivial? The ones I linked to in my opening post perhaps? A page like Caffeine (data page) may be a bit harder, because it seems to duplicate much of the info that is already in the infobox on the main page. Lead(II) nitrate (data page) seems like a quite average, typical "data page". Perhaps the "Material Safety Data Sheet" should not be converted, as it is not our business to make statements like "It is highly recommended that you seek the Material Safety Datasheet (MSDS) for this chemical from a reliable source such as those below, and follow its directions." Fram (talk) 14:35, 1 April 2014 (UTC)

Same footer box should also be available for {{infobox drug}} articles, I think. So that's chembox, elements and drugs. I hope this ambition is no too small. -DePiep (talk) 18:06, 1 April 2014 (UTC)

What to include? Well, let's include all data in there. Make it a stand-alone full data sheet. This relieves us from the "how important" discussion per data fact per article. Of course there is a limit, the encyclopedic one, and the low-prose. But not by level of detail. That data sheet can include the whole infobox (chembox, element, drug). Some detailed info then could go out of the infobox. I guess other infoboxed pages (like with {{infobox building}}) have the same issue. -DePiep (talk) 06:55, 2 April 2014 (UTC)

I've never worked much with the data pages, though I was aware of their existence. In my view, the chembox in the top-right corner is important, and should carry the pertinent data for the compounds, the important (I know that it is a subjective term) properties - I think we can agree about boiling and melting points, density, refractive index, vapour pressures, commonly used alternative names, links to appropriate similar compounds. Some are 'edgy' - I can see the crystal lattice constants for important crystalline compounds (CaSO4, also found as a mineral, water ('common ice'-variety), but for others that is information that is less generally 'useful' (crystals of ethanol? Anyone outside of specific corner of chemistry would even encounter crystals and have use for the lattice constants?) and then that data should be 'separate'.

Providing structured information has different considerations from presenting information designed for human narrative. WikiPedia should support both. In addition, finding downloadable, structured, information of even the most basic sort is a challenge. Ironically, information which you could download from a FTP site a few years ago (e.g. a CSV table of compound solubility in H₂O at various temperatures) is increasingly 'hidden' behind easy to use web sites and (not always so easy to use) web services. If you need to look up the solubility of potassium permanganate at 5°C w/ pH 4.5, there are a few sites you can use, as well as many software applications. Having a complete library of 3d molecular files similarly isn't something everyone needs, as you can get these readily via PubChem, PDB, etc.

• Now if you wanted to do some custom analysis or development (e.g. If I want to figure out some combination of organic indicator and/or redox reaction w/ a pretty color endpoint to allow semi-quantitative detection of transition elements--and as colorimetric titration end point--in geological samples prepared under field conditions with a high likelihood of having variable amounts of Cu, Fe, Mn, Ni, Ti and Al in every sample) you have to do a lot of cut-paste, convert-table-to-text, cut-paste, save-as-csv to get it into a reasonable relational database to start and see if a satisfiable combination exists. This is not as much fun as it sounds.
• While the Merck & CRC Handbook will always have value beyond just holding the top of my scanner down firmly enough to press out wrinkles, it should be possible this day in age to do for general chemistry needs what has been going on in geographic information systems.
• I am coming at this from the perspective of a clinical bioinformaticist, where I have a glut of downloadable indexed data (but never close to what I need) from PDB, KEGG, DrugBank, etc. etc. If I wanted to make a quick and dirty clinical decision support system that you could feed a list of a person's prior/chronic diagnosis, a few laboratory tests, allergies and current medications and tell you what medication you could prescribe for a new problem you can download tabular sources you could use as part of the solution. While these don't all get replicated on WikiPedia, they have FTP/HTTP download sites link from their respective WikiPedia article.
• This makes having data pages a very valuable addition to other representations.
• Having large amounts of use tabular information (e.g. pH of a MeOH/KOH solution at different [KOH], H₂O content and temperature) in the body of an article would be detrimental to readability and load speed.
  • Doesn't every chemical compound deserve having, at least, data pages for their solubility (based on solvent, temp and pH) and similar (e.g. pH based on solvent, temp and concentration), as well as other helpful reference information (e.g. spectral data, participation in chemical reactions, thermodynamic values under non-STP conditions, etc.)?

--DrKC MD (talk) 20:37, 18 April 2014 (UTC) I think it is the best that a 'second' chembox-like template would be constructed, which goes into the bottom part, is page-wide, and is standard collapsed. It should have most of the parameters from the chembox (except maybe for the parameters which will ALWAYS be mentioned in the chembox if known, like boiling point and the common chemical identifiers), and probably also parameters which will never appear in the chembox (IR-absorption-frequencies, NMR-signal positions, multiplicity, and intensity, maybe even images of spectra?). It could have a modular approach like the chembox, but with multiple columns

My suggestion: everything can go into the bottom box, the data in the chembox should either be that which are either common and are related to readily observable properties (melting point & boiling point -> is it a solid, liquid, gas; density - heavier or lighter than water; colour - how does it look like), or are of interest significantly outside of the field of chemistry for that chemical (the example of crystal structure, if the compound is relating to minerals, it links to mineralogists and to the-man-in-the-street with an interest in minerals (hobby)). It might make some of the massive chemboxes a bit smaller if some data was moved, and some data could be compacted (some chemboxes have data for 4 stereoisomers and the racemate, whereas the-man-in-the-street generally only encounters one specific stereoisomer (in the case of medicine or natural products), or only the racemate - move the data for other 4 to the bottom box). --Dirk Beetstra ^{T C} 08:29, 2 April 2014 (UTC)

Yes. Some additional points. The discussion to put data "above" or "below" is less tough that "in" or "out". It will occur, but less problematic. If the box is to be treated as a stand alone data sheet (I suggest), all info should be there (repeated from chembox). This stand-alone idea would be more practical if one can print it separately. Technically, there is no need for "modular" treatment any more as {chembox} does, Lua can handle hundreds of parameters easily. The problem will be how to document them useful! Remember that we want to merge the chem, drug, and element data into this from day one. That's some two dozen+ sections to merge. -DePiep (talk) 08:50, 2 April 2014 (UTC)

Halite/Rock salt

A discussion is taking place on the title of this article at Talk:Halite#Requested_move. All input welcome. Thank you. ^walk victor falk ^talk 15:07, 4 May 2014 (UTC)

Pageview stats

After a recent request, I added WikiProject Chemicals to the list of projects to compile monthly pageview stats for. The data is the same used by http://stats.grok.se/en/ but the program is different, and includes the aggregate views from all redirects to each page. The stats are at Wikipedia:WikiProject Chemicals/Popular pages.

The page will be updated monthly with new data. The edits aren't marked as bot edits, so they will show up in watchlists. You can view more results, request a new project be added to the list, or request a configuration change for this project using the Tool Labs tool. If you have any comments or suggestions, please let me know. Thanks! Mr.Z-man 02:31, 4 June 2014 (UTC)

Leaflet For Wikiproject Chemicals At Wikimania 2014

Hi all,

My name is Adi Khajuria and I am helping out with Wikimania 2014 in London.

One of our initiatives is to create leaflets to increase the discoverability of various wikimedia projects, and showcase the breadth of activity within wikimedia. Any kind of project can have a physical paper leaflet designed - for free - as a tool to help recruit new contributors. These leaflets will be printed at Wikimania 2014, and the designs can be re-used in the future at other events and locations.

This is particularly aimed at highlighting less discoverable but successful projects, e.g:

• Active Wikiprojects: Wikiproject Medicine, WikiProject Video Games, Wikiproject Film

• Tech projects/Tools, which may be looking for either users or developers.

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For more information or to sign up for one for your project, go to:
Project leaflets
Adikhajuria (talk) 11:25, 13 June 2014 (UTC)

Request review: edits by a party with commercial interests (Agmatine)

An editor claiming to be Gad M. Gilad, Ph.D. has recently made substantial changes to Agmatine. Please see my comments on Talk:Agmatine. The editor is a scientist who sells agmatine supplements (neurofencine). I do not assume the edits were made in bad faith; however, after a very brief look, I have found at least one statement that strikes me as questionable (again, see the article's talk page). I would appreciate anyone's efforts to review the recent changes, and remove any that may not have been in good faith. —νημινυλι (talk) 05:33, 21 June 2014 (UTC)

Pesticide Properties Database

The Pesticide Properties Database (PPDB) is linked from > 100 articles. What about creating a template (like in de.wikipedia)? --Leyo 22:45, 24 April 2014 (UTC)

The issue is not to create the template, but to replace the external links by the template in all articles. --Leyo 23:50, 18 May 2014 (UTC)

Is there information in the database that should/could be added to {Chembox}? -DePiep (talk) 00:19, 19 May 2014 (UTC)

I think that it's fine to have the link to PPDB in the External link section, as e.g. in Hydroprene. --Leyo 20:57, 19 May 2014 (UTC)

I created Template:PPDB. It would be good to have it inserted to these articles in an automated manner. --Leyo 22:41, 23 June 2014 (UTC)

Arsenic diiodide

Is the structural formula in the article correct or should it rather be a crystal structure instead? --Leyo 15:08, 23 June 2014 (UTC)

If I understand the the listed NQR article correctly, it does have noticeably covalent bonding with this sort of connectivity. If there is a crystal structure, that would certainly be better (WP:V and also confirm the bonding) than what appears to be a mindless-machine-generated one based on its formula. DMacks (talk) 15:20, 23 June 2014 (UTC)

• It does seem to be discrete, if unstable. Diarsenic tetraiodide would be a more accurate description. There are very few papers on it, most of which are old and in german (nothing secondary) but perhaps you could scrape something useful off these (doi:10.1002/zaac.19663430504) (doi:10.1002/zaac.19663450308)Project Osprey (talk) 15:37, 23 June 2014 (UTC)

  I skimmed through these two papers, but I could not find anything on the actual structure. My knowledge in inorganic chemistry is quite weak.

  The ugly JPG image needs to be replaced anyway. --Leyo 21:46, 23 June 2014 (UTC)

Well that has to be one of the most obscure inorganic things elevated by WP. But see diphosphorus tetraiodide. There's all kinds of these subhalides, just not many people studying them..--Smokefoot (talk) 23:37, 23 June 2014 (UTC)

I can upload the crystal structure of P₂I₄ (which should be same as As₂I₄). It contains these units, which are not bonded to each other and are aligned in the crystal lattice. Would it be better than File:Diphosphorus-tetraiodide-3D-balls.png? Materialscientist (talk) 02:28, 24 June 2014 (UTC)

Structure of Patent Blue V

I don't know much about our standards for diagramming dyes, and would welcome input at Talk:Patent Blue V#Which atoms are charged? for what image(s) to include and what terminology to use for it. DMacks (talk) 03:00, 4 July 2014 (UTC)

c:Commons:VPP#Support for Chemical table files

Just to let you know. --Leyo 12:04, 13 July 2014 (UTC)

Changes in {Infobox element}

We have some 125 element infoboxes (see Category:Periodic table infobox templates). I have prepared changes to change the box into a wiki-standard {{Infobox}}. See Change_Infobox_element_to_use_{Infobox} for an overview and comments. Some questions are open.

You can check your favorite element for changes (e.g., fluorine). An all-parameter demo is here. -DePiep (talk) 13:25, 18 July 2014 (UTC)

Infobox

Hi ... is there an infobox that would be appropriate to use for articles such as Aroma compound? Thanks. --Epeefleche (talk) 21:06, 28 July 2014 (UTC)

I don't think an infobox is necessary. I can't think of a chemistry one that would be appropriate. -- Ed (Edgar181) 11:44, 29 July 2014 (UTC)

Norleucine RM

Hi. Any input at Talk:Norleucine#Requested move would be appreciated. Cheers, Jenks24 (talk) 11:48, 31 July 2014 (UTC)

Aluminium hydride

Could someone with more knowledge (and journal access) than I check out this series of edits to aluminium hydride? They look legitimate, but something in the wording sets off my suspicions. Pi.1415926535 (talk) 13:20, 6 August 2014 (UTC)

I reverted it because it appears to be a blatant citation spamming job for one research group (to Zdan et al.). A not uncommon occurrence here. It would probably be worth rechecking this literature. --Smokefoot (talk) 13:37, 6 August 2014 (UTC)

Thanks for looking. Are the BPilgrim77 edits the same editor and same spamming? Pi.1415926535 (talk) 15:40, 6 August 2014 (UTC)

New articles on hemiaminals

A series of new articles on hemiaminals were recently created. I'm concerned that these are non-notable compounds. In fact, I'm not sure that they even exist except theoretically or perhaps transiently (they will readily decompose into an aldehyde and ammonia). All the articles are also unreferenced.

• 1-Aminoethanol
• 1,2-dihydroxyethylamine
• 1-Amino-1-propanol
• 2-Amino-2-propanol
• 2-methyl-1-amino-1-propanol

Should they be kept or nominated for deletion? ChemNerd (talk) 12:52, 15 August 2014 (UTC)

In my book, these articles are non-notable and should be deleted. --Smokefoot (talk) 13:09, 15 August 2014 (UTC)

I think they should get the chop. No one seems to have written about them. It looks to be some kind of amateur "WP:OR" with neologisms for Glycaminol, seraminol, Sympropaminol, Propaminol, Valaminol, and Alanaminol. In other writings most uses of the term "1-Aminoethanol" seem to be an error for "2-Aminoethanol". I don't think redirecting to a related substance will be helpful. But if there is an article that explains whey they don't exist, they could be redirected to that (I don't know of such). Graeme Bartlett (talk) 22:25, 15 August 2014 (UTC)

for years now we have been accepting chemicals pages without question and there must be millions of them. it is odd to just start blocking these type of articles now. If or not stable non-notable isomers exist seems relevant to me and Wikipedia could fill this gap where other sources fail. Chemspider on the melting point of 1-aminoethanol cites the "Jean-Claude Bradley Open Melting Point Dataset" but that dataset cites a commercial supplier. This commercial supplier does not have the compound in its inventory. 1-aminoethanol does not deserve a dedicated page but should be discussed in the context of 2-aminoethanol. V8rik (talk) 13:11, 16 August 2014 (UTC)

I don't think it's really true that we have accepted such pages without question in the past. Pages like these often end up at being proposed for deletion or put through AFD. All articles on chemical compounds need to meet the general notability guideline. Based on a cursory look, I don't think these ones do. -- Ed (Edgar181) 00:30, 18 August 2014 (UTC)

Perhaps they could treated under a general article named "Geminal amino alcohols". If not an article, then perhaps a new section under Alkanolamines. However, such a new section are constrained by the article name to pertain only to saturated amino alcohols, and would prevent the possible future treatment of unsaturated amino alcohols. FYI, they're not hemiaminals, but they are aminols. Plasmic Physics (talk) 00:47, 18 August 2014 (UTC)

Here are some more...

• Tryptophaminol
• Tyrosaminol
• Phenylalanaminol
• Prolaminol
• Isoleucaminol
• Leucaminol
• Threonaminol
• Methylcystaminol
• Pentaminol
• Butaminol
• Methionaminol
• Cystaminol

I have invited Zuloo37, the creator of all these articles, to contribute to the discussion here. -- Ed (Edgar181) 00:35, 18 August 2014 (UTC)

The way I saw it, no one had written about these yet, and they seemed important. While it is true that in water, they can decompose into ammonia and an aldehyde, we only experience such an event on this oxygenated planet. I feel like life on other planets (ex. Titan, with liquid methane) could possibly use poly amino alcohols as proteins rather than the oxidized amino acids. 1-Aminoethanol and 2-Aminoethanol are isomers, but they are both real compounds with different properties that I think deserve independent pages. Using the same language as for amino acids, but simply adding "aminol" seems to describe them pretty well, I think. Moving them to a Geminal amino alcohol page or adding a new section on the Amino alcohol page is a good idea. I made models for all the compounds and started making the articles, hoping that people would consider them and find their properties. One of the pages I made already had properties added to it, 1-Amino-1-propanol. Even if they are unstable in a strong solvent like water, the pages should still exist and say why they're unstable, because I see no reason for them to be, if using ammonia or methane as a solvent. -- User:zuloo37 (User talk:zuloo37) 03:55, 18 August 2014 (UTC)

We really need some references that show these exist, and what they are called, and other interesting things about them. Do you know of any? Graeme Bartlett (talk) 22:13, 18 August 2014 (UTC)

I found a few references for Aminomethanol and 1-Aminoethanol, but I wasn't able to find anything for 1,2-dihydroxyethylamine, which is a little disappointing. -- User:zuloo37 23:34, 18 August 2014 (UTC)

Why on earth start an article if without decent references? One recommendation is to redirect most of these things to Alkanolamine. --Smokefoot (talk) 02:01, 19 August 2014 (UTC)

They are not aminals. Plasmic Physics (talk) 07:09, 19 August 2014 (UTC)

OK, I slightly compressed the 1-Aminoethanol, which I figured was kind of a parent and I didnt want to get zuloo37 too depressed, and redirected 1-Amino-1-propanol to alkanolamine. If this arrangement seems satisfactory, I will convert the other "esoteric" members to redirects. --Smokefoot (talk) 14:46, 19 August 2014 (UTC)

what could be done is create a table for a listing of these other alkanolamine members with some selected properties, that could also include the molecular models. Example for reference: Boronic_ester#Boronic_acids V8rik (talk) 16:32, 19 August 2014 (UTC)

Good idea about the table, perhaps within the article on alkanolamines. I found no review on these species but there is a lot of literature, dating back to Liebig. Apparently in anhydrous NH3, a number of these things can be generated and even isolated, although they tend to convert to the hexahydro-1,3,5-triazines or revert back to the aldehydes --Smokefoot (talk) 17:57, 19 August 2014 (UTC)

It's really not satisfactory to have them all redirect to Alkanolamine. A table of Geminal amino alcohols that includes structure would be better. Though I feel Wikipedia would benefit more if all the pages for the compounds existed, to let them be edited to include more information over time as more articles about these amino alcohols appear. I also noticed that there isn't a page for Methoxyamine.. --User:zuloo37 12:17, 20 August 2014 (UTC)

Here's a good way to start an article: Step 1 find a WP:SECONDARY reference (a review, book etc). For example, if you want to go with Methoxyamine, you could start with doi 10.1002/047084289X.rm192m.pub2. Articles that other editors suspect are at the edge of notability often get blended with a larger article. In this way the readers are served (we are not here to serve editors) by being able to see the small topic in a grander context, such as hemiaminal. If the small topic grows within the grander one, then it can be spun off. At least that is my perspective. In the case of the carbinolamines listed above, readers would be deprived of the RN and some physical properties that were in the thin ChemBoxes. This content would be represented in the table that V8rik hinted might be a compromise position. Good luck with Methoxyamine, it would be good practice for you.--Smokefoot (talk) 02:40, 20 August 2014 (UTC)

A single article to contain the content of all these articles sounds like a reasonable way forward, provided sufficient sources to support the content can be found. I don't think it would be a good idea to redirect the current titles to the combined article though - these names are made up by Zuloo37 and therefore should not appear on Wikipedia. -- Ed (Edgar181) 12:01, 20 August 2014 (UTC)

Are those names not completely unambiguous? Geminal amino alcohols follow a series that looks just like the amino acids, so why wouldn't it make sense to use the same names as the amino acids? I'm using already well-established names, and simply adding "aminol" to the end. That sounds more like systematic naming than making up names, doesn't it? --User:Zuloo37 17:54 22 August 2014 (UTC)

It doesn't matter that they sound like they might be systematic chemical names, Wikipedia should not be using names that you made up. This falls under one of Wikipedia's central principles that "all material in Wikipedia must be attributable to a reliable, published source" as described at Wikipedia:No original research. -- Ed (Edgar181) 18:03, 22 August 2014 (UTC)

But they don't just sound like systematic names; they ARE systematic, unambiguous names. It doesn't make sense to say that I made them up when they are systematic and based on names of compounds that already exist. I did not "make up" these names, nor did I "make up" these compounds. I found all of my information from first principles, which is why I have no references, but that's also why I feel like I don't need references. I just noticed compounds that no one had put on Wikipedia yet, used unambiguous, systematic names, and added pages. Do you have a better idea for naming this series of compounds that so obviously mirrors (and is essential for the subsequent production of) amino acids? --User:Zuloo37 18:56, 22 August 2014 (UTC)

What you are doing is what wikipedia calls original research: synthesizing the information about some topic (certain known chemicals and their literature information, nomenclature rules, etc.) into being about a different topic (a compound that is not in the literature). That's a worthwhile academic endeavor in some fora, but strictly prohibited here on wikipedia. Instead wikipedia is only for notable specific topics, which means published reliable sources are a non-negotiable requirement. DMacks (talk) 19:33, 22 August 2014 (UTC)

Well, I guess I made these articles early. They'll be notable eventually, because the literature is always expanding. I still think the articles should exist so that people can know the existence of geminal amino alcohols. My "bias" was basing the names of the compounds in the series on the amino acids, but that doesn't change the fact that they are precursors to amino acids. I guess the problem is that since there's no literature for these compounds yet that says they are precursors to amino acids, I'm not allowed to suddenly start using names derived from the amino acids. I understand, but it's pretty frustrating to know that I'm not allowed to contribute original information. --User:Zuloo37 20:09, 22 August 2014 (UTC)

Yup, that's the nature of the wikipedia site, one of its core policies. We're "just an encyclopedia" that writes about what's already been written, not a chat-site or blog for novel work by amateur (or even professional!) scientists. I think you still have a core intellectual claim: you think they will be notable "eventually", but even that prediction is based on nothing except your own (meta-)analysis of other literature (people actually study people who study things, and you don't seem to have a reference handy that "eventually everything that can be studied will be studied and those studies reported". For the case at hand, wikipedia is not a crystal ball; if and when in the future a topic reaches the threshhold for notability to be an article, an article would be welcome. There are presumably plenty of blogs for budding scientists to discuss and propose ideas, and of course hundreds of research groups on various related chemistries who might take an interest in some topic if someone were to join them and make a scientific case for researching it. DMacks (talk) 20:24, 22 August 2014 (UTC)

I can aggregate some of the useful content of the not very notable articles into hemiaminal. Now, I am wondering about alkanolamine, which probably should be about alkanolamines that are not hemiaminals. I had started to subdivide alkanolamine into 1,2- and 1,1- (gem) varieties, but am reconsidering that approach.--Smokefoot (talk) 13:34, 20 August 2014 (UTC)

Why reconsider? Geminal and vicinal seem like apt sectioning. Plasmic Physics (talk) 22:16, 20 August 2014 (UTC)

Well I was thinking that carbinolamine covers the geminal variety. --Smokefoot (talk) 22:21, 20 August 2014 (UTC)

Compare hemiacetal with geminal diol. In the former, the structure requires a non-hydrogen group on the second oxyl group in the same way as a hemiaminal requires one or more non-hydrogen groups on the amino group. Plasmic Physics (talk) 22:35, 20 August 2014 (UTC)

OK, I was wondering about that. Perhaps this weekend I will dig into this. --Smokefoot (talk) 13:16, 21 August 2014 (UTC)

I started an article for Geminal Amino Alcohol and made a table with pictures. --User:Zuloo37 22:02, 22 August 2014 (UTC)

I redirected Geminal Amino Alcohol to hemiaminal, which is the same theme, it seems. Plasmic Physics might have some thoughts on this option vs the other pre-existing article on alkanolamine. But we probably dont need three master articles on RR'C(OH)(NHR"). We eventually might put a lot of this list into an appendix since they are rather esoteric --Smokefoot (talk) 05:05, 23 August 2014 (UTC)

I'm finding the term "aminocarbinol" (sometimes more specifically "gem-aminocarbinol") often used for this substructure in the literature. But the context is actually in fairly complex molecules, as unstable metabolic intermediates produced by oxidation of secondary or tertiary amines. They go on to fragment (losing either water or the amine to give C=NR or C=O via simple equilibrium) or additional oxidation (OH becomes carbonyl, meaning an amide functional group). They're also known as intermediates in various standard organic transformations, such as the Weinreb ketone synthesis (where it's stable at low temperatures) and amide reduction (where it's not stable). I could envision an article on this structural motif itself. DMacks (talk) 08:25, 23 August 2014 (UTC)

And to prove how important context is for nomenclature, "aminocarbinol" is also standardly used as the name for 4-amino-2-cyclopentene-1-methanol, which does not contain this functional group. DMacks (talk) 08:34, 23 August 2014 (UTC)

Agree that the class RR'C(OH)(NHR") is notable, although I am skeptical the individual articles recently initiated. Also we assume that RR'C(OH)(NHR") = aminocarbinol = carbinolamine, which is the redirect to hemiaminal. --Smokefoot (talk) 12:42, 23 August 2014 (UTC)

Comment on the WikiProject X proposal

Hello there! As you may already know, most WikiProjects here on Wikipedia struggle to stay active after they've been founded. I believe there is a lot of potential for WikiProjects to facilitate collaboration across subject areas, so I have submitted a grant proposal with the Wikimedia Foundation for the "WikiProject X" project. WikiProject X will study what makes WikiProjects succeed in retaining editors and then design a prototype WikiProject system that will recruit contributors to WikiProjects and help them run effectively. Please review the proposal here and leave feedback. If you have any questions, you can ask on the proposal page or leave a message on my talk page. Thank you for your time! (Also, sorry about the posting mistake earlier. If someone already moved my message to the talk page, feel free to remove this posting.) Harej (talk) 22:47, 1 October 2014 (UTC)

ESIS: service closed

The ESIS website closed its service. There are lots of articles that now have a dead link: Special:LinkSearch/esis.jrc.ec.europa.eu. I guess that we need to find alternative links as replacements. --Leyo 04:53, 19 November 2014 (UTC)

The {{chembox}} template should probably be modified for now so that the "| EINECS = " field no longer links to this website. That would eliminate most of the dead links. If an alternative link is found, it could be added to chembox later. -- Ed (Edgar181) 12:59, 19 November 2014 (UTC)

There might be a possibility to link to the ECHA search result somehow. --Leyo 18:45, 19 November 2014 (UTC)

GHS pictograms will be deleted January 1. 2015

I just saw on commons that the GHS pictograms (, , etc.) will be deleted January 1. 2015. We are using them a lot. Maybe the license can be changed to {{PD-ineligible}}...? Christian75 (talk) 16:59, 18 November 2014 (UTC)

Neither of those two files appears to be tagged for deletion. Got a link to where this thing was you saw on commons? DMacks (talk) 17:37, 19 November 2014 (UTC)

GHS symbols are intended to be used internationally as universal warning signs. The UN normally waves copyright when it makes things like this, so I can't imagine why they would be up for the chop. Project Osprey (talk) 17:50, 19 November 2014 (UTC)

User:Leyo edited the description of the files after I wrote here, see [2] - so its fixed :D Christian75 (talk) 20:15, 19 November 2014 (UTC)

Ethyl sulfate info box errors

I am copying comments I made on the ethyl sulfate (ethyl hydrogen sulfate) page to here. I am not sure how to go about getting this corrected.== Boiling and melting point. The boiling and melting point given are the same as for diethyl sulphate. This strikes me as very unlikely. I have verified that diethyl sulphate has the boiling and melting points listed, but I cannot find the values for ethyl hydrogen sulphate. I am almost sure that these have been mixed up, and it should say that the values are unknown if the correct values cannot be determined.Stainless316 (talk) 13:41, 13 November 2014 (UTC)

Further digging on data

This reference http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=162221653#x27

gives BPt 209.5 with decomposition and MPt -25°C - exactly the same as diethyl sulfate. However, this reference also gives specific gravity/density as 1.172 - similar to diethy sulfate's wiki entry of 1.2, rather than wiki entry for ethyl hydrogen sulfate of 1.46. The reference often specifically refers to diethyl sulfate in other sections. I believe that this reference has mixed up ethyl hydrogen sulfate and diethyl sulfate. It also seems likely that this mix up has occurred elsewhere, and has been mis-applied in the wiki entry. I cannot find the boiling point and melting point of ethyl hydrogen sulfate.Stainless316 (talk) 13:12, 14 November 2014 (UTC)

I noticed this because I needed to know the boiling point for ethyl sulfate, and the incorrect information was a problem for me.Stainless316 (talk) 09:53, 25 November 2014 (UTC)

Chemspider- is it sensible to link all inorganic compounds?

Take Sodium metasilicate as a simple example. The anhydrous form contains a polymeric anion. The hydrated forms contain discrete silicate ions with 4 coordinate silicon. Chemspider names the compound as disodium oxosilanediolate with an image that shows SiO₃^2– anions, implying that there are indeed three coordinate silicate anions present.

I queried their structure for sodium aluminium silicate, (which they take to be NaAlSi₂O₆, the mineral jadeite) which shows discrete SiO₃^2– with a systematic name of "Aluminium sodium oxosilanediolate (1:1:2)" . I got this response.

"To explain ChemSpider is a database of chemical structures, but only stores primary structure data -things at the molecular level (atoms, bonds etc) it does't hold data on supramolecular or extended structures (eg how molecules are arranged in ordered materials) - nor can it distinguish between two materials that have the same molecular structure but different supramolecular structure - for instance Calcite, aragonite and vaterite are all percieved as the same. But we can provide links out to resources that do have pages/entries that do distinguish these materials."

Molecules in calcium carbonate- whatever next. Chemspider has an "RSC" endorsement so should be considered to be authoritative. If it were any other site that showed such a structure we wouldn't link, would we? Axiosaurus (talk) 11:29, 29 November 2014 (UTC)

Missing CAS numbers

Could someone with SciFinder access check, if there is a CASRN for the following compounds?

• Agmatidine
• Base J
• Lithium imide

Thank you. --Leyo 23:45, 5 December 2014 (UTC)

Done. However there is an issue with Base J, I have a CAS No for the compound in the chembox (53910-89-7), but the article already has a CAS No (53910-96-6) which correspond to compound 3 in the left-hand image (sort-of). Any idea which compound is the core one? Project Osprey (talk) 14:02, 8 December 2014 (UTC)

Thank you. No, I don't know, but maybe Edgar181 who added the other CAS RN just yesterday knows more.

Concerning the CAS RN of agmatidine you added, it is sort of surprizing that there are only two (strange) Google hits. --Leyo 18:02, 8 December 2014 (UTC)

SciFinder structure-search (including an alternate tautomer of the cytosine-imine region) confirms the CAS and only lists 12 refs. DMacks (talk) 19:29, 8 December 2014 (UTC)

The CAS No I added to Base J came from ChemSpider. Please feel free to replace it if you think it is wrong. -- Ed (Edgar181) 19:09, 8 December 2014 (UTC)

• Done. With added refs. --Project Osprey (talk) 10:13, 9 December 2014 (UTC)

Copper(II) carbonate

I have made extensive corrections to this article. (CuCO₃ is not known or at best is very unstable - the article described the basic carbonate, Cu₂(OH)₂CO₃), malachite). Can someone with admin please move the article to "basic copper carbonate" and change copper(II) carbonate to a redirect. I have removed a lot of chembox info. relating to the so called CuCO₃ that points to chemspider etc so could someone please check I have got rid of all the relevant flags etc. I have assigned the CAS # using the Rubber bible. Thanks. Axiosaurus (talk) 10:33, 12 December 2014 (UTC)

I moved it, It would not have taked an admin to do this! I have not checked infobox flags, as I do not know how to use them either. Graeme Bartlett (talk) 00:41, 13 December 2014 (UTC)

Free 'RSC Gold' accounts

I am pleased to announce, as Wikimedian in Residence at the Royal Society of Chemistry, the donation of 100 "RSC Gold" accounts, for use by Wikipedia editors wishing to use RSC journal content to expand articles on chemistry-related topics. Please visit Wikipedia:RSC Gold for details, to check your eligibility, and to request an account. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 10:49, 23 December 2014 (UTC)