Wikipedia talk:WikiProject Chemistry/Archive 46

Aromatic alcohol definition
I've found this problem checking Wikidata entries. I think you have an error in the definition of aromatic alcohol. The difference between aromatic alcohol and phenol is that in phenols hydroxy group is bonded directly to an aromatic ring (not neccesarily benzene ring) and in aromatic alcohols it is bonded indirectly (usually to the benzylic position). Right now definition in aromatic alcohol states that phenols = aromatic alcohols (however, Category:Aromatic alcohols says something different). Regards, Wostr (talk) 13:51, 21 July 2018 (UTC)
 * That is a substandard article that might be deleted. It is not supported by good references.  It was created by a sockpuppet.  I have no idea of the meaning of an "aromatic alcohol".  Wikipedia has phenols, to which I propose to redirect aromatic alcohol, unless others disagree.  BTW, phenols is in rough shape.  It describes a large class of compounds.--Smokefoot (talk) 13:58, 21 July 2018 (UTC)
 * ChEBI defines "aromatic alcohol" as "Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring." In my experience, this usage is not common ("benzylic alcohol" is clearer and less ambiguous vs phenol) and is also not the meaning used in our aromatic alcohol article (no requirement of the structural distance). The Manual of Scientific Style (I have no idea what standards-body is affiliated with this!) says "Aromatic alcohols (phenols) have the general formula Ar—OH." and this usage seems to be present in the literature. But other sources clearly define phenols as being a disjoint set of hydroxyl functional group vs alcohols rather than a subset (IUPAC Gold Book specifically defines "alcohols" as OH attached to a saturated position). I think we are best with WP:TNT and writing a brief statement that the term is ambiguous, with pointers to the benzyl-alcohols and phenols articles. DMacks (talk) 20:46, 21 July 2018 (UTC)
 * Concur with TNT. --Smokefoot (talk) 23:33, 21 July 2018 (UTC)
 * Smokefoot redirected the title to phenols, which I think is the best thing to do for now. -- Ed (Edgar181) 13:24, 25 July 2018 (UTC)
 * No objection. I just did the same for Aromatic alcohols so that the plural and singular point to the same place. Would be interesting to scan WP for singular-vs-plural redirects that point to different targets, or where one is a redir to not-the-other. DMacks (talk) 13:42, 25 July 2018 (UTC)
 * That would be an interesting search. Maybe suggest it at Wikipedia talk:Database reports?  -- Ed (Edgar181) 13:59, 25 July 2018 (UTC)
 * I posted at VPT (it also relates to a WP technical restriction). DMacks (talk) 14:10, 25 July 2018 (UTC)
 * Okay, thanks for solving this problem, but there is still Category:Aromatic alcohols. Wostr (talk) 20:26, 26 July 2018 (UTC)

Covalent bond or not ?
Curating data in WD I often have a problem with metal oxides where some representations show them as ionic compound and others as covalent molecules. See for example zirconyl nitrate:
 * Pubchem CID 11953300 with an ionic bond between oxygen and zirconium
 * Pubchem CID 11506893 with a covalent bond between oxygen and zirconium

These different structures have a strong impact on structural identifiers like InChI, InChIKey or SMILES.

Similar problem for complex like sodium hexacyanoferrate:
 * Chebi indicates covalent bonds between cyanide and iron giving OBOWFEZVRNRJBU-UHFFFAOYSA-N as InChIKey
 * Pubchem indicates ionic bonds giving GTSHREYGKSITGK-UHFFFAOYSA-N as InChIKey.

Is there any good reference or rule to define which structure is the better in order to define only one possibility as structural identifier ? Snipre (talk) 15:45, 25 July 2018 (UTC)
 * "Don't trust PubChem structures" is my first rule for...well almost anything. But especially for things with metals or complex 3D forms. For example consider ferrocene:
 * The disproval of CID 504306 was a major historical breakthrough that established the field of X-ray crystallography.
 * CID 21938862 doesn't even have the correct chemical formula.
 * DMacks (talk) 15:57, 25 July 2018 (UTC)


 * For your first case, anhydrous zirconyl nitrate (what your two CIDs illustrate) might not even exist whereas several hydrates do. But the structure of the pure hydrate seems to be a bridged polymeric chain and at least some zirconium–nitrate structures have bidentate nitrates.10.1007/s11172-005-0222-7 And what the heck even is CID 83761? DMacks (talk) 16:16, 25 July 2018 (UTC)
 * Pubchem seems to be maintained for bio-organic chemists, so it is not reasonable to rely on that database for structures of metal compounds. But within English Wikipedia, we are pretty careful with structures.  If you see any structures that are suspect, please leave a note here! Zirconium is a tough one, as DMacks suggests. --Smokefoot (talk) 16:25, 25 July 2018 (UTC)
 * Thanks for your comment, but can you give me a better reference database ? Or any other references ? Snipre (talk) 12:37, 27 July 2018 (UTC)

In some ways it may not matter as neither SMILES or InChI can correctly represent anything other than fully organic compounds. If you follow the rules correctly salts and organometallics become 'Disconnected' to give you free metal ions and organic ligands. You do sometimes see people create accurate looking structures by playing around manually, but you often find that these 'hacked' SMILES or InChI strings give different outputs on different software (octahedral bonding can be particularly troublesome). --Project Osprey (talk) 13:43, 27 July 2018 (UTC)

Ethanol
I noticed late last night that an anon added the hazards template to ethanol, but inadvertently seems to have referenced and copied data from a calcium hydroxide reference for the PEL limits. I tagged it not in citation. Would someone please correct this error? Jim1138 (talk) 17:37, 29 July 2018 (UTC)

Often unsourced changes to NPAP 704 NFPA-H field
There are quite a few changes to teh NPAP 704 NPAP_h= field on the in ethanol, methanol (most common), and carbon dioxide articles. Sometimes or. I often run across this while doing wp:RCP. What can be done to prevent this? Jim1138 (talk) 17:37, 29 July 2018 (UTC)

Help requested re chemical formula subscripts
At I've asked for help regarding the possible ambiguity of subscripts. —&#91;  Alan M 1  (talk) &#93;— 23:20, 31 July 2018 (UTC)

oxidized fats
I noticed this redirect, which points to a specific cardiovascular disease article. I find that this makes little sense, since there should be many topics for this particular term. Do we have an article on the oxidation of fat? -- 65.94.42.168 (talk) 05:54, 31 July 2018 (UTC)
 * Rancidification? --Project Osprey (talk) 09:48, 31 July 2018 (UTC)
 * I've changed the target to that as being significantly better Galobtter (pingó mió) 18:15, 1 August 2018 (UTC)

Silicic acid
The AfD for Silicic acid was recently closed with a decision to keep, but the article itself could stand cleanup, I think. XOR&#39;easter (talk) 15:33, 29 July 2018 (UTC)
 * OK, "silicic acid" was speedily deleted, which probably violates some policy or other about what to do with recently AfD'ed pages, but more importantly it makes the page history inaccessible. Silicic acid is now a redirect to silicon dioxide, and silicic acids is an article. XOR&#39;easter (talk) 17:34, 1 August 2018 (UTC)
 * Could you check whether User:Galobtter managed to get everything back to the previous state? Silicic acid appears to be a full article with an extensive history (the only deleted revisions relate to page-moves and redirects) and Silicic acids is a redirect to it with no useful editorial history (nor anything in its deleted history). I could envision a good-faith discussion about whether the singular or plural should be the actual page-name for this apparent non-specific compound name. Is it in the realm of Manual of Style/Chemistry/Compound classes or simply an ambiguous term? If it were to be plural, that doesn't automatically mean the singular should redirect to a different meaning (see WP:PRIMARY and WP:TWODABS). DMacks (talk) 18:07, 1 August 2018 (UTC)
 * Yeah I moved it back as it most likely shouldn't suddenly redirect to Silicon dioxide after 13 years of remaining an article, possibly breaking many of the links in and things like that (silicates may be a better target anyhow if one wanted to redirect it). - the information on the 2017 synthesis is good but probably should be integrated with the historical information in the previous version of Silicic acid.. Galobtter (pingó mió) 18:13, 1 August 2018 (UTC)
 * It looks like everything is in the right place &mdash; thank you very much! Whatever improvements need to be made now can probably happen through the day-to-day course of editing. XOR&#39;easter (talk) 13:27, 2 August 2018 (UTC)

Curaxins
Draft:Curaxins 2 is an Articles for Creation submission dealing with a family of anti-cancer molecules that needs attention from a subject matter expert. It would be great if someone could help out. Thanks! Catrìona (talk) 22:59, 6 August 2018 (UTC)

Nascent iodine
Someone might consider modifying the lede of Nascent iodine (dietary supplement) to indicate that the concept of nascency has been debunked. The problem is that the concept is so thoroughly debunked that if might be difficult to get a source. But for those naive readers wanting to read up on nascent iodine, we owe it to them to say that there is no such thing.--Smokefoot (talk) 02:11, 6 August 2018 (UTC)
 * Nascent state (chemistry) has some sources that look promising. Double sharp (talk) 02:16, 6 August 2018 (UTC)
 * ✅ and thank you. --Smokefoot (talk) 00:21, 7 August 2018 (UTC)

Debate on the correct values for the pKa of water and hydronium
A number of Wikipedia articles concerning acids (e.g. strong acids, hydronium, pKa, etc.) are not in agreement when discussing the pKa of water and hydronium. This inconsistency reflects an ongoing "debate" on which standard state should be used when calculating the values. The most recent (and comprehensive) papers to discuss this topic are:
 * J. Chem. Educ., 2017, 94 (6), pp 690–695 DOI: https://doi.org/10.1021/acs.jchemed.6b00623
 * Helv. Chim. Acta, 2014, 97 (1), pp 1-31 DOI: https://doi.org/10.1002/hlca.201300321

Briefly, depending on the mathematical convention used for standard state, the pKa for water is listed as either 14 or 15.7 and the pKa for hydronium is listed as either 0 or -1.74. When using the standard and agreed upon conventions of thermodynamics, the values of pKa are 14 and 0 for water and hydronium, respectively. Unfortunately, however, an overwhelming number of standard textbooks (introductory chemistry and organic chemistry) have relied upon using a non-standard convention that results in the values of 15.7 and -1.74. Depending on the article (and sometimes even the section of article), Wikipedia currently uses a combination of the values. I propose that we begin to clear up this issue by making the articles more consistent. This is a big undertaking since these values are likely to be found in a large number of individual articles. Furthermore, I would like to achieve at least some consensus among editors prior to taking this on. Thanks! JCMPC (talk) 16:57, 29 April 2018 (UTC)
 * Indeed, even Properties of water used to have 15.7 as the pH in the infobox until I changed it (among my early edits, actually) and why I put two references for the pKa and a note. Investigation into the history reveals that from ~2006 (basically when it was inserted), till 2016 when I changed it, it was 15.7, which is somewhat disturbing IMO. Anyhow, I'd definitely say that changing instances of 15.7 to 14 would be good to do. Galobtter (pingó mió) 17:27, 29 April 2018 (UTC)
 * I have a feeling that, until authors of organic chemistry textbooks switch to the standard thermodynamic convention, the value will likely be edited back and forth for some time on Wikipedia. Are any other editors willing to help out on making the switch to make articles more consistent? JCMPC (talk) 14:37, 5 May 2018 (UTC)
 * It looks to me like you guys are missing a factor in your argument. A standard convention does not reflect the real value of something. It is simply the chosen value for making empirical and theoretical coparrisons. For example, just because the IUPAC standard convension for ambient temperature and pressuren is 25 degrees Celcius and 100 kPa, does not mean that the location that you are in has those conditions. i.e. Just because some institution decides that the standard convension for the pKa water and hydronium is 0 and 14, does not make it so in reality. I strongly suggest that if you insist on retaining both sets of pKa values, that you make that non-standardised ones the primary set. Plasmic Physics (talk) 23:02, 5 May 2018 (UTC)
 * Yes, it is widely known that the definition of any standard state is arbitrary and is, in a great many cases, corresponds to an idealized value that is not even physically realizable (e.g. gaseous water does not exist at a partial pressure of 1 bar at a temperature of 300 K but we can still tabulate enthalpies of formation for water under those conditions). The advantage of using the widely accepted definition of thermodynamic standard states is not that these values are correct under all conditions (because they're not), but that they make it easier to communicate measurements and ideas. One of the main points of classical thermodynamics is to determine how factors such as pressure and temperature affect quantities such as equilibrium constants. As long as a standard value is known, it is possible to convert it to another set of conditions. So I guess I don't see the advantage to using non-standardized versions as the primary set of values. Wouldn't this be like supporting a non-standard definition of the meter? Sure one could always come up with a conversion factor to convert between standard and non-standard definitions of the meter, but why go through all the trouble when we can all just use the same definition? JCMPC (talk) 01:00, 17 May 2018 (UTC)
 * That is not a very accurate comparison - there is no notable use for a non-standard meter outside of discussions of the notion, whereas real, non-normalised pKas are useful to the entire field of analytical chemistry. It is simply not appropriate to use standard pKas within high precision fields. Furthermore, the ChemBox, as it is named, is first and foremost intended to collate chemical information before general thermodynamic information; and yes, I realise that there is some overlap, which is why I suggest the ordering of the pKas if both are included. Plasmic Physics (talk) 05:19, 17 May 2018 (UTC)

'''The value -1.76 is simply -log10(55.5). It has nothing to do with acid dissociation. 55.5M is the molarity of pure water.'''

The criterion for classifying an acid as "strong" is that it is fully dissociated in solution. The following table shows the calculated degree of dissociation of a monobasic acid, AH, at a concentration of 1M, as a function of pKa. Dissociation will be greater, the lower the concentration of the acid.

This shows that, in general, an acid may be classified as "strong", if its pK value is less than about -2. That this value is close to -1.76 is purely fortuitous. Petergans (talk) 21:27, 13 August 2018 (UTC)

ChemInform
I just created this. Feel free to expand/correct whatever I got wrong. Headbomb {t · c · p · b} 16:45, 17 August 2018 (UTC)

Unsourced NFPA 704 and hazards
Someone who geolocates to Kurgan, Kurgan Oblast, Russia is adding numerous unsourced. I opened a ticket on WP:ANI. If people wish to chime in, please do. Jim1138 (talk) 21:21, 17 August 2018 (UTC)

Facto Post – Issue 15 – 21 August 2018
MediaWiki message delivery (talk) 13:23, 21 August 2018 (UTC)

Carbon monoxide-releasing molecules
Carbon monoxide-releasing molecules is an article that I started a long time ago. It is a small area of research with potential clinical applications. Recently the article has been greatly expanded by a single highly focused author. It would be helpful if someone would help out because I cant go it alone and would just end up in an edit war over an article someone thinks they own.--Smokefoot (talk) 13:23, 18 August 2018 (UTC)
 * From the point of view of inorganic chemistry, I find nothing objectionable in the current text. The extensive use of very short sub-sections is not helpful. An important aspect, which I don't think was covered properly, is the absorption and release of CO by haemoglobin. This is particularly relevant to tobacco smokers. The key issue there is that the equilibrium constant for the reaction Hb-CO Hb + CO strongly favours the CO complex, so the release of CO, even in someone who has stopped smoking, takes some time. (c.f. haemoglobin  + cyanide) Petergans (talk) 18:58, 18 August 2018 (UTC)
 * excellent point. this is a problem for CORM therapeutics to overcome in the delivery of CO to a target. Hb is essentially an irreversible sink until the CO is exhaled. this will be added in the days ahead. Ketoacids (talk) 19:41, 19 August 2018 (UTC)

Seeking additional feedback to the recent expansion Ketoacids (talk) 13:25, 21 August 2018 (UTC)
 * As I have expressed previously, Carbon monoxide-releasing molecules is illustrates aspects of what Wikipedia should not be, IMHO. The guiding policy for citations are WP:SECONDARY and WP:TERTIARY.  It is the kind of article that is promotional, almost fawning.  The absence of a meaningful user page precludes perspective on the WP:COI issue.  But Wikipedia is a big organism, and my dissatisfaction with this article is unimportant.  --Smokefoot (talk) 13:47, 21 August 2018 (UTC)
 * Promotional? How so? The question is- does the new technical information provide a sufficient synopsis of the CORM field? If not, how can we make it better? Citation formatting is a concern we are working through. — Preceding unsigned comment added by Ketoacids (talk • contribs) 14:16, 21 August 2018 (UTC)
 * Who is this "we", ? Galobtter (pingó mió) 14:20, 21 August 2018 (UTC)
 * you, me, Smokefoot, David notMD, Wikignomes, the various authors/editors of this topic- (not the 'royal we', incase you're a Lebowski fan). I am sensitive to the fact it is not my page. We are working together to make a better Chem Wiki.Ketoacids (talk) 14:35, 21 August 2018 (UTC)
 * It is your page. No experienced editor would create such a accumulation of specialized factoids and citations, which can seem cherry-picked.  As of today, 598 patents, articles, reports describe CORMs, 108 of these citations have appeared since 2017 (SciFinder).  Savvy editors dare not select among so many papers, lest we introduce bias (WP:UNDUE and WP:NOTNEWS).  Instead, savvy editors kick back, Lebowski-style, and give an encyclopedic overview, citing a few reviews. My 2 cents. --Smokefoot (talk) 17:08, 21 August 2018 (UTC)

Borane nomenclature
There is an issue with the titles of WP articles which are almost identical. The following are examples that I have picked up today. Where present, a number in parentheses indicates the number of hydrogen atoms. Is this is issue covered by IUPAC rules on nomenclature? If not, I suggest that all article titles should indicate the number of hydrogen atoms. e.g. borane(3) instead of just borane. Any suggestions? Petergans (talk) 17:09, 24 August 2018 (UTC)
 * borane and boranes.
 * diborane, diborane(4) and diborane(2)
 * pentaborane and pentaborane(11)
 * hexaborane and hexaborane(12)
 * Before offering my suggestions, the community here owes you a big thank-you for cleaning up these articles. Borane in particular was filled with nutty and spurious verbage.
 * My suggestions:


 * borane and boranes.
 * Leave them alone. To me "borane" is completely unambiguous, even though there are many "boranes".


 * diborane, diborane(4) and diborane(2)
 * Leave them. Every chemist knows what "diborane" is. A famous species. The pair diborane(4) and diborane(2) of interest to a small handful of theoreticians. They have names that set them apart.


 * pentaborane and pentaborane(11)
 * pentaborane should be pentaborane(9) for uniformity with the other B-H clusters and to distiguish it from things including pentaborane(11). Good catch.


 * hexaborane and hexaborane(12)
 * Good catch, I converted hexaborane into a listing of hexaborane(10) and hexaborane(12). And created hexaborane(10).--Smokefoot (talk) 18:15, 24 August 2018 (UTC)
 * I fixed your hexaborane fix, as it was a Cut and paste move (against Wikipedia policy and violates content-license terms) rather than a proper renaming. I also agree that diborane should remain as the specific B2H6 compound, as this is clearly the WP:PRIMARYTOPIC for this name. For others that are less-known, and cases where none are well-known, more specific names and a WP:DISAMBIGUATION at the simple name are good. Although CHEM and WP-wide MOS generally prescribe using singular for compound-classes, "boranes" is a good name for this class because "borane" itself is a definite specific chemical (this approach is equally supported by WP-wide MOS and CHEM apparent current practice). DMacks (talk) 21:49, 25 August 2018 (UTC)
 * please see the WP:HATNOTE regarding what is reasonable/unreasonable for see also entries. For example, someone going to diborane (about one specific chemical with this name) might reasonably be looking for a different chemical with this name that has a more-specifically-named article (diborane(2) or diborane(4)). But one would not likely be at the specific name di borane looking for the more general term of boranes or borane. They are certainly conceptually related and do/could/should link to each other. DMacks (talk) 22:05, 25 August 2018 (UTC)

Draft:Spectroscopy of Multiply Ionized Atoms
A review of this draft is requested. Should it be accepted into article space? Robert McClenon (talk) 01:01, 28 August 2018 (UTC)
 * If there was an article on history of spectroscopy or multiply ionized atoms then the content would have a place to merge to, after trimming, but it is hardly suitable for a standalone topic - WP:COATRACK. Graeme Bartlett (talk) 12:08, 2 September 2018 (UTC)

Chromogen
The chromogen page may need improvement. The definition seems incomplete.

Currently, chromogen is defined as a precursor to a colored molecule.

I am more familiar with this definition:

"In simple terms, it can be considered that the organic dye molecules contained three main components such as chromogen, chromophore and auxochrome. • The chromogen is a chemical compound that is either colored or could be made colored by the attachment of suitable substituent. The chromophore and the auxochrome(s) are also part of the chromogen (Carmen and Daniela 2012). • The chromophore is a chemical group that is responsible for the appearance of color in compounds (the chromogen) where it is located. The colorants are sometimes also classified according to their main chromophore (e.g., azo dyes contain the chromophore –N=N–) (Iqbal 2008). • The auxochrome is a substituent group found in a chromogen that influences its color. Whereas, the chromophore or chromophoric group is responsible for chromogen which will be colored. The chromophore itself is not capable of determine a particular color and hue (Marsden 1982). Also, Gurr differentiates two types of auxochrome namely colligators, which are responsible for dye– substrate interactions and which are either ionic (e.g., acidic: –SO3 −, –COOH, etc., or basic: –N+, –NH2) or non-ionic and non-colligators which modify color (Burkinshaw 2016)."

https://www.springer.com/de/book/9783319338903 https://www.springer.com/cda/content/document/cda_downloaddocument/9783319338903-c2.pdf?SGWID=0-0-45-1564155-p179965151

Anyone agree/oppose to updating the page based on this reference? Ketoacids (talk) 12:47, 25 August 2018 (UTC)
 * Well, I repeat questions posed previously:

--Smokefoot (talk) 14:19, 25 August 2018 (UTC)
 * do you think that you can actually edit following WP:SECONDARY/WP:TERTIARY or is this revision going to be another literature cherry-picking campaign? Your record on Carbon monoxide-releasing molecules is unpromising.
 * Will you write a user page for yourself so that fellow editors can understand potential areas of expertise and COI?

I have reduced the page contents to a selection of definitions found in various dictionaries. Petergans (talk) 16:19, 2 September 2018 (UTC)

Template:Branches of chemistry
Hello. I work essentially in the Portuguese version of Wikipedia, which has serious problems in Chemistry related articles. I found one template which in my opinion is confused, and it's basically the same in English version. It's about Template:Branches of chemistry, which connects different areas in three main topics. I think it's a kind of arbitrary definition, some of that areas (eg Polymer chemistry, Physical organic chemistry, Pharmacy, Surface science, Geochemistry, Solid-state chemistry, Materials science, etc) are actually the result of mixing the three main topics (Physical, Inorganic and Organic Chemistry) with others scientific areas. I wonder if it wouldn't be better in a template such as in the Template:Branches of biology case, without these divisions. Att, Rafael Kenneth (talk) 20:46, 20 August 2018 (UTC)


 * Hey guys, no opinion? Isn't it possible to understand what I've said? Rafael Kenneth (talk) 04:10, 13 September 2018 (UTC)


 * Well I understand what you say, but I think that the organisation is OK. It is easier to see what is there than the more compact biology nav template. Graeme Bartlett (talk) 12:16, 13 September 2018 (UTC)

Talk:Unbibium
FYI there is an RFC at Talk:Unbibium regarding whether a page at that title should now exist. shoy (reactions) 19:18, 24 September 2018 (UTC)

3DMet article: substance needed
I have created article stub 3DMet, since "3DMet" is used in Chembox (144x). An editor asked for more substance, since it does need some sourcing & notability notes. Pls take a look & an edit. -DePiep (talk) 07:28, 29 September 2018 (UTC)
 * ping - DePiep (talk) 07:29, 29 September 2018 (UTC)
 * Maybe we could use a navbox re Chemical database (and ). Or Chemical ID (identifiers only, ); does this overlap with Authority control? -DePiep (talk) 11:36, 29 September 2018 (UTC)

Chembox
I've just finished a review of phosphoric acid. Once again, the clumsiness of the chembox is apparent. A large chembox like this one forces an editor to put pictures and tables on the left and generally leaves less space for the article text. What about mobile phone access?

Here is a suggestion: make all the categories collapsible, with "collapsed" as default setting, A chembox could look like this It will then be easy for a user to show a single category and view its contents, rather than having to trawl through a long list to find what he/she is looking for. Petergans (talk) 15:52, 12 August 2018 (UTC)
 * Making the boxes collapsible is reasonable and could certainly be helpful for the extremely full chemboxes. But those situations are the minority, so if the sections become collapsible, then uncollapsed should be the default state.  -- Ed (Edgar181) 18:08, 12 August 2018 (UTC)
 * I'm not a fan of auto-collapsed tables as a rule. If it is better for mobile access then at least go with default un-collapsed on browsers and default collapsed on mobile view. --Project Osprey (talk) 19:25, 12 August 2018 (UTC)
 * Also, "collapsed" (i.e., by [show/hide] button) does not exist in mobile view. In mobile, it will allways show uncollapsed. This too is why one must design for 'uncollapsed'.
 * In a wider view: the desire to collapse an infobox has this inconsistency: if you want to collapse parts, that part does not qualify for a WP:INFOBOX. For, this contradiction stems from the habit to make the infobox into a data sheet as well. So it tries to square the circle: infobox = main info &mdash; datasheet = complete info. Personally, I think this could best be solved by moving minor data into a "Data sheet" section, leaving main info into in the infobox. Same with and . -DePiep (talk) 12:20, 29 September 2018 (UTC)

Facto Post – Issue 16 – 30 September 2018
MediaWiki message delivery (talk) 17:57, 30 September 2018 (UTC)

Ternary compound and Tertiary (chemistry)
I've come across these sets of what seem to me like very similar articles: Ternary compound and Tertiary (chemistry), Quaternary compound and Quaternary (chemistry). Are these four distinct topics, or two topics unduly spread across four articles? And where does Quaternary phase fit into the picture? – Uanfala (talk) 09:27, 2 October 2018 (UTC)
 * Quaternary compound and Quaternary (chemistry) look to be the same topic. But Ternary compound and Tertiary (chemistry) are very different subjects. Graeme Bartlett (talk) 11:20, 2 October 2018 (UTC)


 * Quaternary phase is (sort of) the four-element equivalent of ternary compound (which deals with three elements) and binary compound (that deals with two elements). These deal with compounds based on the number of different elements in the compound.  Quaternary phase, though, is more a materials science term.
 * Tertiary (chemistry) and quaternary (chemistry) are related terms in organic chemistry dealing with substitution patterns. Quaternary compound is a badly written article overlapping with quaternary (chemistry) and the two should probably be merged.  The former seems to confuse a quaternary cation with an ionic compound containing a quaternary cation, and the latter deals with quaternary compounds whether the quaternary centre is cationic or neutral.  EdChem (talk) 12:24, 2 October 2018 (UTC)

Donna Strickland, case study in ...
If anyone is interested in a real mess/fiasco/mistake/whatever, take a look at Talk:Donna Strickland for some expert handwringing,, wiki-lawyering, and shoulda-woulda. Apparently the article on this weeks's Nobelists Donna Strickland had been deleted as not notable. Of course that changed on Tuesday.--Smokefoot (talk) 12:31, 4 October 2018 (UTC)
 * Oh dear... that is a blazing PR disaster. Looks like the page was originally deleted for copyright infringement rather than notability. There was also a parallel draft which was declined due to lack of references. Obviously some confusion as to what's actually happened there - not that it matters now as its already hit the news. — Preceding unsigned comment added by Project Osprey (talk • contribs)

"Bromtoluolklorid"
Hi. I just started an article about Alfred Wahlforss, who researched subtance called "bromtoluolklorid" in Swedish, "bromtoluolikloridi" in Finnish. I could not find the definite English term, but suppose that it is bromotoluene chloride. Is this correct? Many thanks, --Gwafton (talk) 19:43, 3 October 2018 (UTC)
 * I'd guess it's e.g. 4-bromo-3-chlorotoluene or any of its nine(?) other isomers. --Leyo 23:33, 3 October 2018 (UTC)
 * It's Br-C6H4-CH2Cl, I think para. This according to:
 * DMacks (talk) 02:13, 4 October 2018 (UTC)
 * You are right. BTW: ChemSpider, ECHA --Leyo 07:13, 4 October 2018 (UTC)
 * Sorry, my knowledge in chemistry is limited. So by what name shall I call the chemical in the article text? --Gwafton (talk) 18:53, 4 October 2018 (UTC)
 * Like most chemicals, there are several names in use. I would probably go with para-bromobenzyl chloride, as it makes clear that this is a derivative of benzyl chloride. Yilloslime (talk) 19:47, 4 October 2018 (UTC)
 * The article is now edited with the correct name. Many thanks for all who helped. --Gwafton (talk) 21:05, 4 October 2018 (UTC)
 * Thanks for working on it! Just for everyone's reference, Alfred Wahlforss is the article. DMacks (talk) 18:25, 5 October 2018 (UTC)
 * Thanks for working on it! Just for everyone's reference, Alfred Wahlforss is the article. DMacks (talk) 18:25, 5 October 2018 (UTC)

Nomination of 3DMet for deletion
A discussion is taking place as to whether the article 3DMet is suitable for inclusion in Wikipedia according to Wikipedia's policies and guidelines or whether it should be deleted.

The article will be discussed at Articles for deletion/3DMet until a consensus is reached, and anyone, including you, is welcome to contribute to the discussion. The nomination will explain the policies and guidelines which are of concern. The discussion focuses on high-quality evidence and our policies and guidelines.

Users may edit the article during the discussion, including to improve the article to address concerns raised in the discussion. However, do not remove the article-for-deletion notice from the top of the article.

Deletion of this artice would give a redlink in the lefthand side. DePiep (talk) 15:26, 15 October 2018 (UTC)

Removal of 3DMet data from
At the moment, the article about 3DMet (one in the ), is up for deletion (AfD). Reason is lack of WP:NOTABILITY, as measured by ~not being referenced in secondary (independent) sources. IOW, virtually no sources refer to it as useful etc. or actually use 3DMet.

If and when this article is deleted, it follows that the data row (3DMet in Chembox) should be removed too (we should not link or point to an irrelevant and not-notifyable database). Today, some 126 articles use parameter 3DMet:.

The only way to save this information is to prove notability of 3DMet by adding secondary sources (read the AfD though for an investigation already made into this: few sources are sound).

Parameter was added in 2007. -DePiep (talk) 07:19, 19 October 2018 (UTC)
 * If the article were to be deleted, why would that require that we remove the 3DMet parameter from the Chembox? -- Ed (Edgar181) 17:26, 19 October 2018 (UTC)
 * Talk central is here. I'll reproduce your argument there shortly. -DePiep (talk) 19:46, 19 October 2018 (UTC)

Base modifying agent
Can anyone with some knowledge of chemistry advise me if this is a notable term that needs its own article, or can it be redirected elsewhere? I don't know enough about chemistry to determine if the few short book sources I've found on GBooks are reliable or sufficient. I'm happy to do any required legwork. &spades;PMC&spades; (talk) 21:17, 18 October 2018 (UTC)
 * And also heterosaccharide? &spades;PMC&spades; (talk) 08:59, 26 October 2018 (UTC)
 * Heterosaccharide looks to me like a WP:DICDEF, and either a neologism or a misnomer for heteropolysaccharide. A sugar-cotaining monomer is a glycoside. Pectin is a polymer, and an example of a heteropolysaccharide. I suggest redirection (redirects are cheap, and someone might come across or misremember the correct name). Narky Blert (talk) 12:27, 26 October 2018 (UTC)
 * Perfect, I like that. &spades;PMC&spades; (talk) 12:30, 26 October 2018 (UTC)

Facto Post – Issue 17 – 29 October 2018
MediaWiki message delivery (talk) 15:01, 29 October 2018 (UTC)

A link to a DAB page
Polycarboxylates links to the DAB page threshold effect. I am (or, was) an organic chemist, and the relevant sentence puzzles me. It's unclear where calcite is (not) being deposited - on laundry or equipment? Has anyone got any ideas for resolving this problem? The best I can think of, is that it's a muddled way of saying that calcium will stay in solution while there's free sequestrant around. Narky Blert (talk) 12:10, 26 October 2018 (UTC)
 * I'm also perplexed. I just removed it. Yilloslime (talk) 02:38, 31 October 2018 (UTC)

Please consider
Whether http://chemister.ru/ is an appropriate reference source for the English encyclopedia, relative to alternatives, especially given that its tabular information on chemical compounds appear without any sources. See for instance, reference 1 of the citric acid article. The standard for all article information, even in the infobox, is reliable, traceable sourcing, and not just the appearance of values that allow one to complete the desired fields. 2601:246:CA80:3CB5:74A5:20A6:5D83:76ED (talk) 20:15, 4 November 2018 (UTC)

zinc isopropyl xanthate
Could some kind soul with chemical drawing software and a spare moment on their hands please make me a picture of zinc isopropyl xanthate? I really would be most grateful. --Project Osprey (talk) 16:04, 7 November 2018 (UTC)
 * These things are deceptive. Dithioacid derivatives of zinc are typically pentacoordinate.  Most crystal structures are for adducts with py etc.  It is this aspect that complicates writing simple articles on the dithiophosphates and dithiocarbamates etc.   Turns out that Zn(S2CO-iPr)2 has been crystallized and is in the Cambridge Database and I could produce a drawing.  doi 10.1107/S0567740872004881.  .... but it is a tetramer.  This article has the structure of pyZn(S2COEt)2: DOI 10.1071/CH9760731.--Smokefoot (talk) 17:25, 7 November 2018 (UTC)




 * Many thanks but I was only looking for a simple skeletal formula. I'm trying redo our articles on vulcanization and sulfur vulcanization. Various agents are involved, all with uncommon functional groups, so it seemed wise to add pictures.--Project Osprey (talk) 17:47, 7 November 2018 (UTC)
 * Xanthates are used? There is this image too. Zinc bis(dimethyldithiocarbamate)




 * Any thiocarbonyl based functional group seems to do the trick. Xanthates are used for latex. I've already used that image to illustrate dithiocarbamates.--Project Osprey (talk) 00:04, 8 November 2018 (UTC)

Arsonic acids
Can someone with Chemistry knowledge please check this new page out. How is this different from Arsenous acid? Both articles reference the formula H3AsO3. Also, there is Arsonic acid. I don't know enough to evaluate if they are covering the same subject. Thanks.  Onel 5969  TT me 15:53, 8 November 2018 (UTC)
 * The situation:

--Smokefoot (talk) 17:37, 8 November 2018 (UTC)
 * Arsonic acid does not exist. Its tautomer arsenous acid does exist.  It is a common form of arsenic.
 * Since we have articles on chemicals that dont exist, we have Arsonic acid. The article is essentially a disclaimer that it does not exist (much).
 * strangely, although arsonic acid itself is exceedingly rate, many organoarsonic acids are known. Essentially replace the As-H in HAs(O)(OH)2 with As-organic. R groups do not migrate well (might be an interesting rsch project).  These organic compounds, some of which are fed to chickens, are described under arsonic acids, emphasis on the plural.

Hype city
Cyanostar, check it out.--Smokefoot (talk) 00:52, 8 November 2018 (UTC)
 * It is now toned down somewhat, but so little is written on this molecule that it is hard to make a useful Chembox. Graeme Bartlett (talk) 08:12, 9 November 2018 (UTC)

Add to Chembox a link to MetaCyc database?
Here people maintaining MetaCyc have proposed to add to Chembox a link option to MetaCyc (external link, like KEGG and PubChem). Please discuss whether this is useful. -DePiep (talk) 08:30, 11 November 2018 (UTC)

Featured quality source review RFC
Editors in this WikiProject may be interested in the featured quality source review RFC that has been ongoing. It would change the featured article candidate process (FAC) so that source reviews would need to occur prior to any other reviews for FAC. Your comments are appreciated. --IznoRepeat (talk) 21:34, 11 November 2018 (UTC)

Carbyne. Why?
There's a chemical compund class namely carbyne and also another chemical specie called by the same name (linear acetylenic carbon - LAC) in a large range of references. Are they related in somehow degree? Or is it just a misconcept? Does someone know where the name carbyne for LAC comes? Rafael Kenneth (talk) 13:52, 12 November 2018 (UTC)

Chembox taskforce
Looking for people interested in helping out with converting Chembox to use Infobox. Anyone interested in taking part, please drop a line here. Thanks! -- Zack mann  (Talk to me/What I been doing) 18:51, 20 November 2018 (UTC)
 * Second attempt. I have a working proof of concept and really need some help! -- Zack mann  (Talk to me/What I been doing) 19:01, 22 November 2018 (UTC)
 * Perhaps this is a sign that chem folks don't support your mission, given you are only asking for help accomplishing it and explicitly blocking discussion of whether it should be accomplished (for technical, time-use, or other reasons)? DMacks (talk) 11:19, 23 November 2018 (UTC)
 * Is there a mock up? Is there a rationale for why the Chembox needs replacing?  --Smokefoot (talk) 12:14, 23 November 2018 (UTC)
 * There's a partial proof of concept at Infobox chemical. From what I can tell this is a technical proposal aimed at changing the backend-code of chembox. The process of creating a chembox that we're use to (putting data into fields) ought not to be affected. --Project Osprey (talk) 14:27, 23 November 2018 (UTC)
 * I am with DMacks here, it is a humongous amount of work where I do not see great benefit for (but good chance to break things ...). And for what it is worth (and what was blocked in the short-lived RfC): I don't like what I see in the examples. --Dirk Beetstra T  C 18:31, 23 November 2018 (UTC)

Do I see it correctly that chembox is now silently replaced? chembox is marked as depracated? --Dirk Beetstra T C 23:37, 25 November 2018 (UTC)
 * I've un-tagged it as out-of-process, and loudly warned those involved to get WP:CONSENSUS before making changes. DMacks (talk) 03:07, 26 November 2018 (UTC)
 * thanks. --Dirk Beetstra T  C 03:22, 26 November 2018 (UTC)
 * it is now proposed for deletion instead. --Dirk Beetstra T  C 03:30, 26 November 2018 (UTC)
 * I've followed up there as well. Thanks for failing to notify the wikiprojects, Zackmann08. DMacks (talk) 03:34, 26 November 2018 (UTC)

(Pentamethylcyclopentadienyl)aluminium(I)
Hi again. Another new article. I'm not even sure that the title (with no spaces) is correct. Could someone take a look at it? Thanks.  Onel 5969  TT me 23:20, 26 November 2018 (UTC)
 * It is one of several articles from Wiki Ed/MIT/Main Group Chemistry (Fall 2018). The articles are of very high scholarly quality, but overspecialized.  Many articles present the results of quantum calculations performed by the submitting editor (e.g. tellurophene).  Beetstra and I tried at one point to remove these obviously OR results, but these students are determined to show-off their dexterity with DFT.  Perhaps a grade is associated with their work.  I guess that once the class is over (soon), someone might go through and discard the OR results.  Overall, it is a little unfortunate that the students are unsupervised and that they fail to understand that Wikipedia is not a forum for super-specialized stuff.--Smokefoot (talk) 12:05, 27 November 2018 (UTC)


 * I haven't noticed as much trouble with students assignments this year, I'm wondering if its just me?--Project Osprey (talk) 12:54, 27 November 2018 (UTC)
 * Check out isocyanate and hydrazine. If one knows nothing but has a word processor, one can write reams about safety, citing sources from across the globe.  There is a fair bit of this puffing up going on by students who, IMHO, are deluding themselves that they are (a) learning anything and (b) helping any reader very much. --Smokefoot (talk) 17:45, 27 November 2018 (UTC)
 * Thanks for the input... obviously, you can see why I'm requesting help on these types of articles. One thing though, if there is OR, it can be removed immediately. If it's re-added, then follow WP:BRD… just a thought. Onel 5969  TT me 13:35, 29 November 2018 (UTC)
 * These students are vying for a grade. It is more efficient and less aggravating to wait for the end of the school term, then do the cleanup. --Smokefoot (talk) 13:43, 29 November 2018 (UTC)

Facto Post – Issue 18 – 30 November 2018
MediaWiki message delivery (talk) 11:20, 30 November 2018 (UTC)

Admin help or advice or something with phenols?
Phenols is a messy article. Its a compilation of a lot of factoids and lists. Phenol is in good shape. Probably phenols needs to be relabeled "Naturally occurring phenols", a change that that requires admin intervention. Wikipedia has some other article with "Naturally occurring ...", so that label could be a useful category and catch-all. If we spin-off "Naturally occurring phenols", then "Phenols" is allowed to grow into the chemistry of phenols, something we need.--Smokefoot (talk) 12:07, 2 December 2018 (UTC)
 * Why does that need admin intervention? One can create Naturally occurring phenols, by a split pointing in its creation to the revid of phenols that the material came from (to retain attribution).  --Dirk Beetstra T  C 12:21, 2 December 2018 (UTC)
 * OK I just split it. Naturally occurring phenols remains messy.  Phenols less so. --Smokefoot (talk) 13:27, 2 December 2018 (UTC)

Two links to DAB pages
Ineos links to the DAB pages DIB and EOA. Those links have been hanging around like H2Sx since November 2016. Anyone any ideas? I used to be an industrial chemist, and have no clue about them (except that EOA might be a duplicate of ethanolamine). Narky Blert (talk) 10:35, 10 December 2018 (UTC)
 * , DIB will be diisobutylene (2,4,4-trimethyl-1-pentene), the dimer of isobutylene, as is made clear by the statement Isoolefins are a family of monoolefins, obtained by oligomerisation of isobutylene. They include a dimer (DIB) and a trimer (TIB) from this INEOS page. Based on this page, I'd guess you are correct that EOA is a duplicate of ethanolamine.  EdChem (talk) 12:07, 10 December 2018 (UTC)
 * Thanks! Narky Blert (talk) 12:14, 10 December 2018 (UTC)

Use of "chem" in chemical equations instead of classical one
Hi, I would suggest to use the template "chem" when writing a chemical reaction, as it's far simpler to write and to modify (in case of mistakes) and has a better impact on the reader. What's more, is more professional. For example, if you write:


 * 2 Na2CrO4 +  2 CO2  +  H2O  →    Na2Cr2O7  +  2 NaHCO3

You may as well use:



The template "chem" is fit for these formulas, so the syntax is easier, the lenght of the source code is halved and the structure is more clear, even for those who are not really into Wikipedia editing. The space occupied by both this structures is more or less the same, so there should be very few problems about page formatting. — Preceding unsigned comment added by Marcodpat (talk • contribs) 07:29, 12 December 2018 (UTC)

Discuss HTML vs. &lt;chem>

 * Several reader-visible problems (affects the general public not just the few editors of a particular article). First is font mismatch vs the general text. Second is that the chemtex version is not searchable in the browser because it might (sometimes or always?) render as a graphic file instead of actual text. See WP:MATHCHEM for several other technical gotchas. DMacks (talk) 07:38, 12 December 2018 (UTC)


 * Not only that, you cannot copy and paste the formula. We should be making things best for our readers, which would include students that may wish to copy and paste the formula, and the chem markup makes that very hard. Graeme Bartlett (talk) 08:29, 12 December 2018 (UTC)
 * From a reader perspective, I find the rendering of the &lt;chem>-code very ugly (though I agree easier to enter): it simply does not fit with the regular text of the document, and as mentioned, it is a graphic, so you cannot copy-paste the 'text' (literally, you even paste an empty image ..). I would actually !vote to replace &lt;chem> with regular writing throughout.
 * Note that we have chemical formula:
 * 2 + 2  +  -->  + 2
 * though that is difficult to edit (if you are a newbie), and results in links to the elements which is not optimal here (heavy overlinked). --Dirk Beetstra T  C 08:47, 12 December 2018 (UTC)
 * Agreed. If we can achieve some sort of consensus, please let's register our preference for normal text for formulas in our MOS.--Smokefoot (talk) 11:13, 12 December 2018 (UTC)
 * This example is WP:OVERLINKING (three time linking to sodium?). Also, no clear need to link to the elements anyway. Should not be our example. -DePiep (talk) 15:34, 12 December 2018 (UTC)
 * Chem does not do the overlinking and I personally quite like it. Galobtter (pingó mió) 16:54, 12 December 2018 (UTC)


 * I strongly prefer normal text instead of the . -DePiep (talk) 13:46, 17 December 2018 (UTC)

Overview of options
So far, we have these options mentioned here:
 * &lt;chem> (TeX) (currently to be avoided)
 * See: WP:MATHCHEM, WP:TeX vs HTML
 * See: WP:MATHCHEM, WP:TeX vs HTML
 * See: WP:MATHCHEM, WP:TeX vs HTML


 * HTML direct
 * 2 Na2CrO4 +  2 CO2  +  H2O
 * Na2Cr2O7 +  2 NaHCO3
 * See:


 * 2 + 2  +  -->  + 2
 * See Chemical formula
 * See Chemical formula


 * 2 Na2CrO4 + 2 CO2 + H2O -> Na2Cr2O7 + 2 Na2HCO3
 * 2 Na2CrO4 + 2 CO2 + H2O -> Na2Cr2O7 + 2 Na2HCO3
 * See Chem2
 * See Chem2

-DePiep (talk) 09:26, 14 December 2018 (UTC)

Discuss between HTML options

 * Templates involved: HTML, Chem, chemical formula, Chem2

I have separated this topic into a new subthread. Hope this helps structured talk. -DePiep (talk) 09:35, 14 December 2018 (UTC)


 * I am in favor of merging the HTML templates into . already is the most editor-friendly and wide-covering, and can be enhanced (expanded) easily. This might take a development track (adjust, test), but that's worth it. Why maintain three versions at all? -DePiep (talk) 09:40, 14 December 2018 (UTC)
 * Hopefully this discussion leads to a revision of MOS.--Smokefoot (talk) 12:13, 17 December 2018 (UTC)
 * could you expand? -DePiep (talk) 13:09, 17 December 2018 (UTC)

Prof to student: "create a wiki page about me" [conclusion: very tacky]
From creating editor notes: "Jin-Quan Yu personally asked me to create this page for him. I am a grad student in Jin-Quan Yu's research lab and Jin-Quan has given consent to the contents of this page."--Smokefoot (talk) 12:13, 17 December 2018 (UTC)


 * The conflict of interest here smells so bad... Perhaps a warning on his talk page is due? EvilxFish (talk) 12:22, 17 December 2018 (UTC)
 * Ok, I finally did that. However my attempts to tone down to hype have been reverted by the obedient student.  --Smokefoot (talk) 12:27, 17 December 2018 (UTC)
 * And there's this Norbornene-mediated meta-C-H activation--Smokefoot (talk) 12:31, 17 December 2018 (UTC)
 * They need Wikipedia to self-validate themselves.
 * Georginho (talk) 18:29, 17 December 2018 (UTC)
 * I have taken the liberty of emailing this guys supervisor and requested that he speaks to the student and tells them to stop. EvilxFish (talk) 11:18, 18 December 2018 (UTC)

Nomination for deletion
I have nominated Norbornene-mediated meta-C-H activation, please feel free to contribute to the discussion. EvilxFish (talk) 11:35, 18 December 2018 (UTC)

Talk:Perfluorinated compound
I requested the move linked above. Please note that the content of Fluorosurfactant partly overlaps with Perfluorinated compound. --Leyo 11:02, 21 December 2018 (UTC)

Facto Post – Issue 19 – 27 December 2018
MediaWiki message delivery (talk) 19:08, 27 December 2018 (UTC)

Polyisobutene
Polyisobutene currently redirects to Butyl rubber but I have nominated it for retargetting to Polybutene. Your comments are invited to the discussion at Redirects for discussion/Log/2019 January 6. Thryduulf (talk) 14:40, 6 January 2019 (UTC)
 * Thank you for finding this oversight. I created a short article on polyisobutene.  Others are welcome to help out or modify.  It turns out that polyisobutene is pretty different from polybutene, so they should have separate articles.  Wikipedia-en lacks experts in polymers unfortunately, but the Germans have got us covered to some extent.  --Smokefoot (talk) 16:03, 6 January 2019 (UTC)

QPNC-PAGE
The article QPNC-PAGE appears to be almost entirely the work of a single-purpose editor and a multitude of sockpuppets. I don't know anything about this subject; someone who does should probably evaluate the content. RockMagnetist(talk) 17:09, 7 January 2019 (UTC)

Purinones
Hello friends, running through the orphaned articles and found Purinones. Is it a notable enough concept that it needs its own article, or could it be upmerged, perhaps to purine? &spades;PMC&spades; (talk) 07:14, 13 January 2019 (UTC)