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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."[1] 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."[2] 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)

@DMacks: 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.[3]
• 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.[4] But the structure of the pure hydrate seems to be a bridged polymeric chain and at least some zirconium–nitrate structures have bidentate nitrates.doi: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)

@DMacks and Smokefoot: 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 here, but inadvertently seems to have referenced and copied data from a calcium hydroxide reference NIOSH Pocket Guide to Chemical Hazards. "#0092". National Institute for Occupational Safety and Health (NIOSH). 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 deleting the source or referencing a photo. 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 Talk:Chemical formula § Subscript ambiguity I've asked for help regarding the possible ambiguity of subscripts. —[AlanM1(talk)]— 23:20, 31 July 2018 (UTC)

oxidized fats

I noticed this redirect oxidized fats, 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'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'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 Wikipedia: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). Petergans - 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 — thank you very much! Whatever improvements need to be made now can probably happen through the day-to-day course of editing. XOR'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)

 Done 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 pK_a. Dissociation will be greater, the lower the concentration of the acid.

pK	% dissociation
1	27
0.5	43
0	62
-0.5	80
-1	92
-1.5	97
-2	99

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 {{Chembox Hazards}}. I opened a ticket on WP:ANI#Unsourced NFPA 704 and Chembox Hazards. If people wish to chime in, please do. Jim1138 (talk) 21:21, 17 August 2018 (UTC)

Facto Post – Issue 15 – 21 August 2018

Facto Post – Issue 15 – 21 August 2018 The Editor is Charles Matthews, for ContentMine. Please leave feedback for him, on his User talk page. To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see the footer. Back numbers are here. Neglected diseases Anti-parasitic drugs being distributed in Côte d'Ivoire What's a Neglected Disease?, ScienceSource video To grasp the nettle, there are rare diseases, there are tropical diseases and then there are "neglected diseases". Evidently a rare enough disease is likely to be neglected, but neglected disease these days means a disease not rare, but tropical, and most often infectious or parasitic. Rare diseases as a group are dominated, in contrast, by genetic diseases. A major aspect of neglect is found in tracking drug discovery. Orphan drugs are those developed to treat rare diseases (rare enough not to have market-driven research), but there is some overlap in practice with the WHO's neglected diseases, where snakebite, a "neglected public health issue", is on the list. From an encyclopedic point of view, lack of research also may mean lack of high-quality references: the core medical literature differs from primary research, since it operates by aggregating trials. This bibliographic deficit clearly hinders Wikipedia's mission. The ScienceSource project is currently addressing this issue, on Wikidata. Its Wikidata focus list at WD:SSFL is trying to ensure that neglect does not turn into bias in its selection of science papers. Links Wikipedia, Wikidata, and citations, a census, August 2 2018, blogpost by Magnus Manske The rise of Wikidata as a linked data source August 6, 2018, by Karen Smith-Yoshimura on OCLC Research blog Where do Mayors Come From: Querying Wikidata with Python and SPARQL, August 1 2018, Parametric Thoughts blog Newspapers On Wikipedia Update: Initial Wikidata Pass 9 August 2018, Mike Caulfield Google Scholar, Web of Science, and Scopus: a systematic comparison of citations in 252 subject categories Alberto Martín-Martín, Enrique Orduna-Malea, Mike Thelwall, Emilio Delgado López-Cózar, arxiv.org, submitted on 15 August 2018 If you wish to receive no further issues of Facto Post, please remove your name from our mailing list. Alternatively, to opt out of all massmessage mailings, you may add Category:Wikipedians who opt out of message delivery to your user talk page. Newsletter delivered by MediaWiki message delivery

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", Ketoacids? 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.

• borane and boranes.
• diborane, diborane(4) and diborane(2)
• pentaborane and pentaborane(11)
• hexaborane and hexaborane(12)

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)

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 Wikipedia: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)

@Petergans: 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 diborane 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:

• 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?

--Smokefoot (talk) 14:19, 25 August 2018 (UTC)

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 Boleyn - DePiep (talk) 07:29, 29 September 2018 (UTC)

Maybe we could use a navbox re Chemical database (and Category:Chemical databases (49)). Or Chemical ID (identifiers only, Category:Chemical numbering schemes (11)); 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

Phosphoric acid	(title)
Structures	show
Names	show
Identifiers	show
Properties	show
…	…

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 {{Chembox}}, 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 — 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 {{Infobox element}} and {{Infobox drug}}. -DePiep (talk) 12:20, 29 September 2018 (UTC)

Facto Post – Issue 16 – 30 September 2018

Facto Post – Issue 16 – 30 September 2018 The Editor is Charles Matthews, for ContentMine. Please leave feedback for him, on his User talk page. To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see the footer. Back numbers are here. The science publishing landscape In an ideal world ... no, bear with your editor for just a minute ... there would be a format for scientific publishing online that was as much a standard as SI units are for the content. Likewise cataloguing publications would not be onerous, because part of the process would be to generate uniform metadata. Without claiming it could be the mythical free lunch, it might be reasonably be argued that sandwiches can be packaged much alike and have barcodes, whatever the fillings. The best on offer, to stretch the metaphor, is the meal kit option, in the form of XML. Where scientific papers are delivered as XML downloads, you get all the ingredients ready to cook. But have to prepare the actual meal of slow food yourself. See Scholarly HTML for a recent pass at heading off XML with HTML, in other words in the native language of the Web. The argument from real life is a traditional mixture of frictional forces, vested interests, and the classic irony of the principle of unripe time. On the other hand, discoverability actually diminishes with the prolific progress of science publishing. No, it really doesn't scale. Wikimedia as movement can do something in such cases. We know from open access, we grok the Web, we have our own horse in the HTML race, we have Wikidata and WikiJournal, and we have the chops to act. Links ImageGrid SPARQL query for the Art+Feminism focus list on Wikidata. Run and then scroll ... The TABernacle tool for Wikidata editing, by Magnus Manske, has been upgraded. Demo with the ScienceSource focus list and main subjects: with a WiDar login you can edit directly in the table cells. Enslaved: People of the Historic Slave Trade, Michigan State University project for a linked open data platform. Quote: "Disambiguating and merging individuals across multiple datasets is nearly impossible given their current, siloed nature." As the Linked Data for Production (LD4P) project finishes its initial two-year cycle and moves into LD4P2, a list of its BIBFRAME and other RDF tools. Machine Learning with and for Semantic Web Knowledge Graphs, detailed slide pack by Heiko Paulheim, University of Mannheim. In Europe, Scientists Need to Share Their Research for Free if They Want Government Funding, Futurism, by Kristin House, 5 September 2018. If you wish to receive no further issues of Facto Post, please remove your name from our mailing list. Alternatively, to opt out of all massmessage mailings, you may add Category:Wikipedians who opt out of message delivery to your user talk page. Newsletter delivered by MediaWiki message delivery

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:

• Wahlforss, Henrik Alfred (1870). Om Bromtoluolklorid (doctoral). Universitetet i Helsingfors.

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)

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 Wikipedia: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 {{Chembox}} a redlink in the lefthand side. DePiep (talk) 15:26, 15 October 2018 (UTC)

Removal of 3DMet data from {{Chembox}}

At the moment, the article about 3DMet (one in the Category:Chemical databases (49)), 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 {{Chembox}} 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=: [5].

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. ♠PMC♠ (talk) 21:17, 18 October 2018 (UTC)

And also heterosaccharide? ♠PMC♠ (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. ♠PMC♠ (talk) 12:30, 26 October 2018 (UTC)

Facto Post – Issue 17 – 29 October 2018

Facto Post – Issue 17 – 29 October 2018 The Editor is Charles Matthews, for ContentMine. Please leave feedback for him, on his User talk page. To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see the footer. Back numbers are here. Wikidata imaged Around 2.7 million Wikidata items have an illustrative image. These files, you might say, are Wikimedia's stock images, and if the number is large, it is still only 5% or so of items that have one. All such images are taken from Wikimedia Commons, which has 50 million media files. One key issue is how to expand the stock. Indeed, there is a tool. WD-FIST exploits the fact that each Wikipedia is differently illustrated, mostly with images from Commons but also with fair use images. An item that has sitelinks but no illustrative image can be tested to see if the linked wikis have a suitable one. This works well for a volunteer who wants to add images at a reasonable scale, and a small amount of SPARQL knowledge goes a long way in producing checklists. Gran Teatro, Cáceres, Spain, at night It should be noted, though, that there are currently 53 Wikidata properties that link to Commons, of which P18 for the basic image is just one. WD-FIST prompts the user to add signatures, plaques, pictures of graves and so on. There are a couple of hundred monograms, mostly of historical figures, and this query allows you to view all of them. commons:Category:Monograms and its subcategories provide rich scope for adding more. And so it is generally. The list of properties linking to Commons does contain a few that concern video and audio files, and rather more for maps. But it contains gems such as P3451 for "nighttime view". Over 1000 of those on Wikidata, but as for so much else, there could be yet more. Go on. Today is Wikidata's birthday. An illustrative image is always an acceptable gift, so why not add one? You can follow these easy steps: (i) log in at https://tools.wmflabs.org/widar/, (ii) paste the Petscan ID 6263583 into https://tools.wmflabs.org/fist/wdfist/ and click run, and (iii) just add cake. Birthday logo Links Now Wikidata is six, Signpost Special Report Find out how @TheContentMine are attempting to mine scientific and medical literature to improve the accuracy of Wikipedia., Wikimedia UK tweet and video ScienceSource and the Semantic Web sciencesource-pmc-licenses tool by Oravrattas to extract Creative Commons license information from PubMed Central pages, created at the Cambridge Wikidata Workshop Whizzy use of SPARQL to map the London Underground system, whizzed past on Twitter. Wikidata birthday events mapped by SPARQL, too d:Wikidata:Sixth Birthday/Message from dev team If you wish to receive no further issues of Facto Post, please remove your name from our mailing list. Alternatively, to opt out of all massmessage mailings, you may add Category:Wikipedians who opt out of message delivery to your user talk page. Newsletter delivered by MediaWiki message delivery

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.[6] 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)

Zn(S2CO-i-Pr)2 tetramer from doi 10.1107/S0567740872004881.

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)

Structure of [Zn(S₂CNEtMe)₂]₂.doi=10.1016/0277-5387(95)00559-5

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)

References

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. Onel5969 ^{TT me} 15:53, 8 November 2018 (UTC)

The situation:

• 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.

--Smokefoot (talk) 17:37, 8 November 2018 (UTC)

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! --Zackmann (^{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! --Zackmann (^{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)

@DMacks: thanks. --Dirk Beetstra ^{T C} 03:22, 26 November 2018 (UTC)

@DMacks: 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. Onel5969 ^{TT me} 23:20, 26 November 2018 (UTC)

It is one of several articles from Wikipedia: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.Onel5969 ^{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

Facto Post – Issue 18 – 30 November 2018 The Editor is Charles Matthews, for ContentMine. Please leave feedback for him, on his User talk page. To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see the footer. Back numbers are here. WikiCite issue GLAM ♥ data — what is a gallery, library, archive or museum without a catalogue? It follows that Wikidata must love librarians. Bibliography supports students and researchers in any topic, but open and machine-readable bibliographic data even more so, outside the silo. Cue the WikiCite initiative, which was meeting in conference this week, in the Bay Area of California. Wikidata training for librarians at WikiCite 2018 In fact there is a broad scope: "Open Knowledge Maps via SPARQL" and the "Sum of All Welsh Literature", identification of research outputs, Library.Link Network and Bibframe 2.0, OSCAR and LUCINDA (who they?), OCLC and Scholia, all these co-exist on the agenda. Certainly more library science is coming Wikidata's way. That poses the question about the other direction: is more Wikimedia technology advancing on libraries? Good point. Wikimedians generally are not aware of the tech background that can be assumed, unless they are close to current training for librarians. A baseline definition is useful here: "bash, git and OpenRefine". Compare and contrast with pywikibot, GitHub and mix'n'match. Translation: scripting for automation, version control, data set matching and wrangling in the large, are on the agenda also for contemporary library work. Certainly there is some possible common ground here. Time to understand rather more about the motivations that operate in the library sector. Links Wikidata and Libraries: Facilitating Open Knowledge, book chapter by Mairelys Lemus-Rojas, metadata librarian and Lydia Pintscher, Wikidata Product Manager, from Leveraging Wikipedia: Connecting Communities of Knowledge (2018) LD4P and WikiCite: Opportunities for collaboration, WikiCite 2018 program abstract, Christine Fernsebner Eslao of Harvard Library Information and Technical Services and Michelle Futornick, Linked Data for Production Program Manager at Stanford University Shell Lessons for Librarians, Library Carpentry lesson At-risk content on Flickr, blogpost 3 November 2018, Andrew Gray Toward an Abstract Wikipedia, recent white paper by Wikidata founder Denny Vrandečić (Google) Account creation is now open on the ScienceSource wiki, where you can see SPARQL visualisations of text mining. If you wish to receive no further issues of Facto Post, please remove your name from our mailing list. Alternatively, to opt out of all massmessage mailings, you may add Category:Wikipedians who opt out of message delivery to your user talk page. Newsletter delivered by MediaWiki message delivery

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 H₂S_x 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)

Narky Blert, 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:

${\ce {2Na2CrO4 + 2 CO2 + H2O -> Na2Cr2O7 + 2 NaHCO3}}$

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. <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 <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 <chem> with regular writing throughout.

Note that we have {{chemical formula}}:

2 {{chemical formula|Na|2|Cr||O|4}} + 2 {{chemical formula|C||O|2}} + {{chemical formula|H|2|O}} --> {{chemical formula|Na|2|Cr|2|O|7}} + 2 {{chemical formula|Na|2|H||C||O|3}}

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 <chem> formatting. I find the supposed advantages of <chem> to be vague ("more professional") or unimportant (shorter length of source code). I agree with the arguments presented by DMacks, Graeme Bartlett, and Beetstra of why plain text is best. ChemNerd (talk) 14:18, 12 December 2018 (UTC)
• <chem> is the only solution in certain circumstances: matrices, multiline formula, images not available as a character (not in Unicode). Also uncommon characters like the triple bond (≡) are not at hand in html code. In general, many chemical notation forms (apart from super/subscripts) are not easily written in html text; they have to be "encoded". <chem> OTOH, does have an intuitive order & setup (though different, and needs initiation/excercise); it is more systematical and expandable in knowledge (always something more to learn, good). WP:MATHCHEM has the documentation & examples to go to.

Sidenotes: In mobile view, the resulting font shows as regular text font (not "ugly" or so different). There is the omnious message "Do not use {{chem}} in citations" because of WP:COINS. I've never felt happy with this: what is wrong?

When the formula is single-line (usually indented), <chem> is not disturbing the regular text with its font-changes. So, when single-line, <chem> may be preferable.

In general, editors writing more complicated chemical formulae should consider learning the LaTex coding. After all, it was designed to create correct and graphically beutiful results. -DePiep (talk) 16:14, 12 December 2018 (UTC)

Then why can't it look beautiful (rather than just professionally aligned layout)? It wasn't until the past few weeks or months that the reaction-arrow was even a single uniform-thickness line! I agree for complicated layout, such as matrices, or lots of equations where we want certain details to align, TeX is awesome. Isn't triple-bond ≡? DMacks (talk) 16:50, 12 December 2018 (UTC)

IMO the "uglyness" originates from two fonts being mixed (serif/nonserif even). That is typographically absolutely not done. By itself, Latex typographically has great whitespace, placement, relativeness etc.. So especially when stand-alone (in a single line), it looks nice. And yes special symbols are available, but they are not "at hand" (a list search needed). The more complicated formulae are easier & nicer with <chem>. But alas, not yet (see post below). - DePiep (talk) 19:07, 12 December 2018 (UTC)

I'm not sure about whitespace. In the original example, it looks like there is too much whitespace between each subscripted number and the (non-subscripted) text that follows. It's as if "subscript 2", which is rendered in a smaller pointsize (not just lower baseline--that's good!), is given the same width as if it were regular pointsize--that's bad. DMacks (talk) 06:33, 13 December 2018 (UTC)

• I cannot recommend any chem tags at the moment because for the next few months we will still have problems created by texvc in combination with a legacy mhchem version that can produce a very different rendering than expected. I am about half through checking all mhchem on all wikis now and removing some of the current workarounds or replacing them with other workarounds (w:de:user:Debenben/mhchem, help is very much appreciated) so that we can remove texvc and the legacy option to get something which does not render different to what you get everywhere else. We are also trying to improve the visual appearance. If you are interested you are welcome to join our commission, see phab:T195861.--Debenben (talk) —Preceding undated comment added 18:36, 12 December 2018 (UTC)
• We have {{chem2}} too. {{chem2|2 Na2CrO4 + 2 CO2 + H2O -> Na2Cr2O7 + 2 Na2HCO3}} gives

2 Na₂CrO₄ + 2 CO₂ + H₂O → Na₂Cr₂O₇ + 2 Na₂HCO₃

and {{chem2|auto=yes|2 Na2CrO4 + 2 CO2 + H2O -> Na2Cr2O7 + 2 Na2HCO3}} gives

2 Na₂CrO₄ + 2 CO₂ + H₂O → Na₂Cr₂O₇ + 2 Na₂HCO₃

Christian75 (talk) 00:04, 13 December 2018 (UTC)

Great, nice. I note the easy & simple keyboard input ("Na2CrO4"). Why would {{chemical formula}} be preferable to this one? (layoput of examples enhanced) -DePiep (talk) 08:49, 13 December 2018 (UTC)

Another example with this template: :and {{chem2|2 [[Sodium|Na2]][[chromate|CrO4]] + 2 [[carbon dioxide|CO2]] + [[water|H2O]] -> Na2Cr2O7 + 2 Na2HCO3}} gives

2 Na₂CrO₄ + 2 CO₂ + H₂O → Na₂Cr₂O₇ + 2 Na₂HCO₃

Christian75 (talk) 06:24, 14 December 2018 (UTC)

Wow, this {{Chem2}} is really great. Look at the /documenation! Both easy keyboard input *and* covering many formula/wiki situations. May be the best HTML option we have (next to the <chem> WP:MATHCHEM option, now on hold/to be avoided apparently). -DePiep (talk) 08:59, 14 December 2018 (UTC)

Ooh nice! That looks convenient. Galobtter (pingó mió) 09:03, 14 December 2018 (UTC)

• I prefer the <chem> version for non-inline equations. There, I consider the fact that the font differs from the general text a feature. --Leyo 10:15, 14 December 2018 (UTC)

From the general point of view of the math extension the different appearance is more a bug than a feature. In principle every letter should have the same appearance in inline and display equations and the mathfont should match the textfont. However normal sans-serif fonts are not suitable for math because you have to distinguish $|\mathrm {l} \mathrm {I} 1\mathbf {l} \mathbf {I} \mathbf {1}$ and $\Im J$ and $\ell lI/$ etc. I guess the font in default skins and applications will remain sans-serif and there will not be a well-accepted sans-serif math font with sufficient coverage in the foreseeable future, so I guess chem will also stay a bit different. You can force the use of sans-serif with \mathsf e.g. ${\mathsf {l}}{\mathsf {I}}{\mathsf {1}}$ but I consider this a bad idea (except for SI base quantity symbols which use sans-serif by convention). I am not sure how much the ambiguity of sans-serif is a problem in chemistry, but when I look at Carbon tetraiodide I prefer sans-serif there as well.--Debenben (talk) 13:11, 17 December 2018 (UTC)

Article carbon tetraiodide has this formula: CCl₄ + 4 EtI → CI₄ + 4 EtCl, illustrating your point wrt the sans-serif problem in a simple chemical reaction. Compare: ${\ce {CCl4 + 4 EtI -> CI4 + 4 EtCl}}$. -DePiep (talk) 13:46, 17 December 2018 (UTC)

Overview of options

So far, we have these options mentioned here:

<chem> (TeX) (currently to be avoided)

<chem> 2Na2CrO4 +  2 CO2 +  H2O  ->   Na2Cr2O7  +  2 NaHCO3</chem>

${\ce {2Na2CrO4 + 2 CO2 + H2O -> Na2Cr2O7 + 2 NaHCO3}}$

See: WP:MATHCHEM, WP:TeX vs HTML

HTML direct

2 Na<sub>2</sub>CrO<sub>4</sub>  +  2 CO<sub>2</sub>  +  H<sub>2</sub>O

Na₂Cr₂O₇ + 2NaHCO₃

See:

{{Chemical formula}}

2 {{chemical formula|Na|2|Cr||O|4}} + 2 {{chemical formula|C||O|2}} + {{chemical formula|H|2|O}} --> {{chemical formula|Na|2|Cr|2|O|7}} + 2 {{chemical formula|Na|2|H||C||O|3}}

See {{Chemical formula}}

{{Chem2}}

{{chem2|auto=yes|2 Na2CrO4 + 2 CO2 + H2O -> Na2Cr2O7 + 2 Na2HCO3}}

2 Na₂CrO₄ + 2 CO₂ + H₂O → Na₂Cr₂O₇ + 2 Na₂HCO₃

See {{Chem2}}

(Please keep this list a factual overview; discussion can be below or in previous section) -DePiep (talk) 09:26, 14 December 2018 (UTC)

Discuss between HTML options

Original post wrt HTML vs. <chem> forked into a HTML (wiki-templates) comparision. The HTML-variants better be discussed here, separately

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 {{Chem2}}. {{Chem2}} 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)

Smokefoot 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#Requested move 21 December 2018

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

Facto Post – Issue 19 – 27 December 2018 The Editor is Charles Matthews, for ContentMine. Please leave feedback for him, on his User talk page. To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see the footer. Back numbers are here. Learning from Zotero Zotero is free software for reference management by the Center for History and New Media: see Wikipedia:Citing sources with Zotero. It is also an active user community, and has broad-based language support. Zotero logo Besides the handiness of Zotero's warehousing of personal citation collections, the Zotero translator underlies the citoid service, at work behind the VisualEditor. Metadata from Wikidata can be imported into Zotero; and in the other direction the zotkat tool from the University of Mannheim allows Zotero bibliographies to be exported to Wikidata, by item creation. With an extra feature to add statements, that route could lead to much development of the focus list (P5008) tagging on Wikidata, by WikiProjects. Zotero demo video There is also a large-scale encyclopedic dimension here. The construction of Zotero translators is one facet of Web scraping that has a strong community and open source basis. In that it resembles the less formal mix'n'match import community, and growing networks around other approaches that can integrate datasets into Wikidata, such as the use of OpenRefine. Looking ahead, the thirtieth birthday of the World Wide Web falls in 2019, and yet the ambition to make webpages routinely readable by machines can still seem an ever-retreating mirage. Wikidata should not only be helping Wikimedia integrate its projects, an ongoing process represented by Structured Data on Commons and lexemes. It should also be acting as a catalyst to bring scraping in from the cold, with institutional strengths as well as resourceful code. Links Zotero Comes to Google Docs, Zotero blogpost by Dan Stillman, 19 October 2018. Category:Wikipedians who use Zotero T115158 Write a Zotero translator and document process for creating new Zotero translator and getting it live in production, long Phabricator thread 2015–17. Zotero Translators, documentation from zotero.org. Home page on GitHub for Zotero translator Javascript Example translator, for Wikisource. m:Structured Data on Commons/Newsletter/2018-12-07 Diversitech, the latest ContentMine grant application to the Wikimedia Foundation, is in its community review stage until January 2. If you wish to receive no further issues of Facto Post, please remove your name from our mailing list. Alternatively, to opt out of all massmessage mailings, you may add Category:Wikipedians who opt out of message delivery to your user talk page. Newsletter delivered by MediaWiki message delivery

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 Wikipedia:Redirects for discussion/Log/2019 January 6#Polyisobutene. 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? ♠PMC♠ (talk) 07:14, 13 January 2019 (UTC)