Wikipedia talk:WikiProject Chemistry/Archive 44

This is an archive of past discussions. Do not edit the contents of this page. If you wish to start a new discussion or revive an old one, please do so on the current talk page.

Archive 40

←

Archive 42

→

Typography of primes

How should we typeset primed locants? See for example section P-14.3.1 of IPUAC 2004 draft for systematic organic nomenclature[1] for the meaning. IUPAC uses slanted marks, which I assume are typographical prime (symbol) characters. Those are hard to type, so I see lots of WP articles (and other sources) use straight quotemarks, or sometimes set in italic font. MOS:STRAIGHT says we should not use curly quotes—and they seem less correct than the other options in this context—and blesses prime characters in some technical cases. So should we go with IUPAC, or simple keyboard, or italic-formatted to get simple keyboard to look like IUPAC? DMacks (talk) 05:35, 20 November 2017 (UTC)

I’ve always used single quote marker (') because they the easiest (and I guess most universal, we’re not all using the same keyboard setup/language and special characters can move around – this might also be a consideration for wikidata). Beyond that: how does everyone else do it? – Scifinder, Chemspider and Sigma must have had to decide this at some point. The only problem is that I don’t know how you reverse-lookup a character to find out what its ASCII is.--Project Osprey (talk) 10:03, 20 November 2017 (UTC)

Reverse-search by copy-paste: [2] (1 character), or [3] (string). -DePiep (talk) 10:39, 20 November 2017 (UTC)

(ec) :Probably better use the formal IUPAC Recommendations (Red Book, 2005) link (pdf, 377 pages):

IR-2.12 PRIMES

(a) Primes (′), double primes (″), triple primes (‴), etc. may be used in the names and formulae of coordination compounds in the following ways:

(i) within ligand names, in order to differentiate between sites of substitution;

(ii) when specifying donor atoms (IR-9.2.4.2), in order to differentiate between donor atoms;

(iii) when specifying configuration using configuration indexes (IR-9.3.5.3), in order to differentiate between donor atoms of the same priority, depending on whether they are located within the same ligand or portion of the ligand.

[example omitted]

(b) Primes, double primes, triple primes, etc. are also used as right superscripts in the Kröger–Vink notation (see Section IR-11.4) where they indicate a site which has one, two, three, etc. units of negative effective charge.

[example omitted]

— NOMENCLATURE OF INORGANIC CHEMISTRY
IUPAC Recommendations 2005, Red Book (2005) p36/pdf-p48

So the Recommendations clearly state "prime", and do not mention superimposing a style (no italics). The simple keyboard-apostroph is not enough; there are HTML names though: ′ -- see Prime_(symbol)#Representations. -DePiep (talk) 10:26, 20 November 2017 (UTC)

Just as a side note: In de.wikipedia the use of primes is recommended (see de:Wikipedia:Richtlinien Chemie#Spezielle Typographie). --Leyo 21:57, 20 November 2017 (UTC)

Just noting: this German guideline says "Do not use the double-prime character, but repeat single-prime". -DePiep (talk) 23:11, 22 November 2017 (UTC)

Note: (a) is about name-writing, (b) Kröger–Vink notation is about formula notation. -DePiep (talk) 23:25, 22 November 2017 (UTC)

To summarise the most common are

HTML	Symbol
′	′
″	″

You should be able to type single, double, triple and quadruple prime symbols on Windows by holding down "alt" and typing 2032, 2033, 2034 or 2057 on the numeric keypad. (Doesn't work for me.)

Or cut and paste these ′ ″ ‴ ⁗ .

Or use the single prime multiple times ′′′′′

All the best: Rich Farmbrough, 22:53, 22 November 2017 (UTC).

Using alt-codes requires registry HKCU\Control Panel\Input Method\EnableHexNumpad to be set to type REG_SZ to value 1 and rebooting. It works for me and is really time-saving (if you memorise alt-codes); and its Alt + + + alt-code. Wostr (talk) 23:20, 23 November 2017 (UTC)

By LaTeX

(from Prime article), quote:

LaTeX provides an oversized prime symbol, \prime (

\prime

), which, when used in super- or sub-scripts, renders appropriately; e.g., f_\prime^\prime appears as

f_{\prime }^{\prime }

. An apostrophe, ', is a shortcut for a superscript prime; e.g., f' appears as

f'\,\!

.

See also WP:MATHCHEM (<chem> formula writing). -DePiep (talk) 09:00, 23 November 2017 (UTC)

MOS

From our WP:MOSNUM, searched for "prime":

Not to be used for minute, second. Not to be used for foot, inch. Yes to be used for arcminute, arcsecond (i.e., with degrees); it says: use double prime (″) not repeated prime. Of course triple prime is not in play here. We should copy that for this question? -DePiep (talk) 09:00, 23 November 2017 (UTC)

Exceptions to IUPAC?

Are there areas in chemistry that explicitly do not follow IUPAC recommandations? (not use prime?) -DePiep (talk) 23:54, 22 November 2017 (UTC)

Organic chemistry joins inorganics in this? -DePiep (talk) 09:00, 23 November 2017 (UTC)

Nomenclature of Organic Chemistry 2013 has Rule P-16.9 PRIMES, pp. 124–129. Technically (in pdf version) normal ' and " are used (eg. "Primes ('), double primes ("), triple primes ("'), etc. are used...") but the symbols are displayed like primes (′) etc. Also ' and " are technically used for quotation marks but looks like ‘ and ’. I can send a copy of these several pages if you want. As a side note: on the basis of Red Book 2005 and Blue Book 2013, pl.wiki Wikiproject Chemistry adopted about year ago that primes, double primes etc. are recommended. Regards, Wostr (talk) 23:12, 23 November 2017 (UTC)

Thanks. I do not understand some parts. You say "primes are used ... BUT the symbols are displayed like primes". The topic is, like: "within chemistry we all know what that high-upcomma means. Now what single symbol do we actually use for that?" If organic chemistry has other guidelines wrt primes, please tell. -DePiep (talk) 23:27, 23 November 2017 (UTC)

Sorry, it's a bit late and my English is not very good. Of course there is no instruction use symbol ... to write prime in Blue Book (neither in Red Book mentioned above). I just wanted to point out that Blue Book tells the same as the Red Book – technically some symbol is used: apostrophe in Blue Book, „0” in Red Book (? that's what I got when trying to copy-paste prime from Red Book) – visually it's prime symbol.
"Primes ('), double primes ("), triple primes ("'), etc. are used..." is a copy-paste quotation from BlueBook in pdf to show exact symbols they used. Compare it with this image (I think they used formatting to get the visual effect of prime using normal apostrophe). So it's clear only how prime symbol should look. Using ' without formatting (cursive) is not enough and (this is my opinion) the easiest way to be typographically and visually correct is to use prime symbol ′. Also, in pl.wiki we use double prime symbol etc., but I'm not sure it's accessible. Wostr (talk) 00:37, 24 November 2017 (UTC)

Thanks again. I get it. I don't know the Blue Book (yet). I conclude that even you, familiar with organic chemsistry, do state that a "prime" symbol must be a true "prime" as the preiter intended. -DePiep (talk) 00:49, 24 November 2017 (UTC)

That's my opinion that true prime symbol should be used. But what I'm trying to say is that IUPAC recommendations won't tell you which symbol (prime/slanted apostrophe/...) should be used as a prime in chemistry. Some IUPAC recommendations are published by RSC, some by De Gruyter (and they have different typesetters, correctors or whoever may be responsible for choosing these symbols). Also IUPAC recommendations are prepared mainly for print and Wikipedia is not – so searchability and accessibility should be taken into consideration. But still, true prime is IMHO better (I think that slanted apostrophe would not be read by screen readers, but I may be wrong). Good night, Wostr (talk) 01:15, 24 November 2017 (UTC)

I see. Well, IMO when IUPAC or whoever says "prime", we use "prime" and then let the graphicer (font designer) how it looks. That's all. (when we don't use aostrophe, the apostrope does not matter).

So organic chemistry is OK too using "prime"? -DePiep (talk) 01:25, 24 November 2017 (UTC)

Organic chemistry uses prime too. Sorry if my earlier comments were confusing more than helpful. Wostr (talk) 15:58, 24 November 2017 (UTC)

Accessibility

I asked WT:Accessibility if they have any comments about screen-reader effects. DMacks (talk) 06:29, 24 November 2017 (UTC)

As for widely used Windows screen readers, Versions of JAWS released in the last few years read "′", "″", "‴", and "⁗" as "prime", "double prime", "triple prime", and "quadruple prime", respectively. NVDA reads "′" as an apostrophe and reads out the other three as unknown characters; if I remember correctly, earlier versions of JAWS behaved the same way. Graham87 14:22, 24 November 2017 (UTC)

At least on the Mac, VoiceOver reads the above symbols as "prime", "quote", "triple prime", and "prime with prime with prime with prime". iOS might be different. Edit: on the iPhone, they are read as "apostrophe", "double quotation mark", "triple prime", and "quadruple prime".Codeofdusk (talk) 17:38, 24 November 2017 (UTC)

Ball-and-stick model

This key chemical article lacks references. Does anyone have got appropriate literature to be added? --Leyo 08:50, 28 November 2017 (UTC)

The article has been defaced with an ugly tag so I cannot do any work on it but I have noticed that the German Wiki has a link to an article (open-access pdf). Need to be able to read German though. V8rik (talk) 21:26, 28 November 2017 (UTC)
This addition has been made today. ;-) I guess that there is also some English language literature on that topic. --Leyo 22:04, 28 November 2017 (UTC)

@V8rik: "The article has been defaced with an ugly tag so I cannot do any work on it..." I'm curious, what does that mean? You can't edit an article that has a note saying that it is unreferenced? ChemNerd (talk) 23:27, 28 November 2017 (UTC)

Exactly! the tag prohibits me from adding any reference it all! We want to strongly discourage people just adding tags and complain instead of adding actual references. We want to strongly encourage people to pro actively add references. And it works! Someone complained in 2010 but did nothing constructive and got no results. Someone else asks a question in 2017 (and within days) with immediate results! V8rik (talk) 19:46, 29 November 2017 (UTC)

Your behavior seems completely irrational to me. It is much more likely to produce the opposite result than what you purport to want. The article remained unreferenced for seven years after being tagged because of editors such as you. ChemNerd (talk) 13:01, 30 November 2017 (UTC)

I am missing something here, with respect to adding references to atricles my track record is excellent V8rik (talk) 16:36, 1 December 2017 (UTC)

No, I'm sorry if I implied that. My curiosity about this minor point is getting the best of me. I just meant refusing to add references to an article that someone has indicated needs references ("the tag prohibits me from adding any reference") comes across as counterproductive. I'll drop the stick now, because I'll just inadvertently upset you more, when I should be instead expressing appreciation to other editors such as you for all the contributions you've made to Wikipedia's chemistry articles over the years. ChemNerd (talk) 18:10, 1 December 2017 (UTC)

Case closed! and thanks for the star! V8rik (talk) 18:36, 1 December 2017 (UTC)

I added a couple of references. ChemNerd (talk) 19:30, 29 November 2017 (UTC)

Class projects again

Just a heads up: it looks like there is an ongoing class project that will affect chemistry articles: Wikipedia:Wiki Ed/Louisiana State University/CHEM 4150 (Fall 2017). I have reverted some off-topic additions to urea and there has been quite a bit of new content added to parabens. More to come, I'm sure. -- Ed (Edgar181) 18:29, 28 November 2017 (UTC)

Based on that Wiki Ed page, it seems their grade will depend on the state of the articles they are editing on November 28. So we can expect them to fight hard for their contributions to be included (regardless of Wikipedia norms) today, and then they will likely just walk away after that. ChemNerd (talk) 19:49, 28 November 2017 (UTC)

That sounds like Wiki edu needs to get involved then. --Izno (talk) 21:23, 28 November 2017 (UTC)

So far as I can tell Wiki ed does zero.--Smokefoot (talk) 01:21, 1 December 2017 (UTC)

No class should be grading students on what "sticks". We emphasize that to instructors at multiple points in the onboarding process. The Dashboard tool they use makes it easy for instructors to see student contributions regardless of whether they're in articles, removed, or still in a sandbox. We're getting in touch with the instructor to make sure that's not the case here. In general, if you see a class that looks to factor the current state of an article into their grades, please post to WP:ENB. --Ryan (Wiki Ed) (talk) 20:27, 1 December 2017 (UTC)

Disambiguation links on pages tagged by this wikiproject

Wikipedia has many thousands of wikilinks which point to disambiguation pages. It would be useful to readers if these links directed them to the specific pages of interest, rather than making them search through a list. Members of WikiProject Disambiguation have been working on this and the total number is now below 20,000 for the first time. Some of these links require specialist knowledge of the topics concerned and therefore it would be great if you could help in your area of expertise.

A list of the relevant links on pages which fall within the remit of this wikiproject can be found at http://69.142.160.183/~dispenser/cgi-bin/topic_points.py?banner=WikiProject_Chemistry

Please take a few minutes to help make these more useful to our readers.— Rod ^talk 14:05, 3 December 2017 (UTC)

One of these is a link from the Natural Product Updates article to the NPU DAB page. Special:WhatLinksHere/NPU says such a link exists, but I can't find it in the article itself. DMacks (talk) 21:34, 3 December 2017 (UTC)

See {{Infobox journal}} code: looks like |abbreviation=NPU → NPU is internally checked for existance, but not shown. -DePiep (talk) 22:05, 3 December 2017 (UTC)

I'm not sure what specific parietal DAB entry should be linked from the Laminin 111 article. I fixed the Sandra Pizzarello article. DMacks (talk) 21:37, 3 December 2017 (UTC)

Thanks for your help with these. This is exactly the sort of issue which needs specialist help.— Rod ^talk 07:57, 4 December 2017 (UTC)

WP:AALERTS need some help on Community Wishlist Survey

Many of you use Article Alerts to get notified of discussions (PRODs and AfD in particular). However, due to our limit resources (one bot coder), not a whole lot of work can be done on Article Alerts to expand and maintain the bot. If the coder gets run over by a bus, then it's quite possible this tool would become unavailable in the future.

There's currently a proposal on the Community Wishlist Survey for the WMF to take over the project, and make it both more robust / less likely to crash / have better support for new features. But one of the main things is that with a full team behind Article Alerts, this could also be ported to other languages!

So if you make use of Article Alerts and want to keep using it and see it ported to other languages, please go and support the proposal. And advertise it to the other chemistry projects in other languages too to let them know this exists, otherwise they might miss out on this feature! Thanks in advance! Headbomb {t · c · p · b} 14:45, 4 December 2017 (UTC)

Periodic table scheduled for TFA

This is to let you know that the Periodic table article has been scheduled to be rerun as today's featured article for January 8, 2018. Please check the article needs no amendments or corrections. I've notified the FAC nominator, StringTheory11 but it's unclear if that user is still active, so I'm posting here too. In particular, if the article has problems that make it unfit to run, let me know as soon as possible so I can run something else Jimfbleak - talk to me? 10:21, 11 December 2017 (UTC)

Thanks. I've notified WT:ELEMENTS, where most talks are going wrt the elements. -DePiep (talk) 10:43, 11 December 2017 (UTC)

Nonsense article?

While looking for orphaned chemistry articles, I found this article, densination, which doesn't make any sense? The only results I can find about it is the latin word densinate..does anyone here have any idea what it's about? Galobtter (pingó mió) 07:10, 12 December 2017 (UTC)

Hi the page you linked seems to not exist. EvilxFish (talk) 09:28, 12 December 2017 (UTC)

Whoops- Densitation. Someone has now tagged it for PROD. Seems correct. Galobtter (pingó mió) 09:55, 12 December 2017 (UTC)

I <3 Wikipedia and it's ability to find nonsense and delete it, if only the same happened in peer reviewed journals ;) . Kind regards EvilxFish (talk) 10:13, 12 December 2017 (UTC)

Talk:Unstable molecules

Where should this redirect? In ictu oculi (talk) 09:38, 14 December 2017 (UTC)

Facto Post – Issue 7 – 15 December 2017

Facto Post – Issue 7 – 15 December 2017

A new bibliographical landscape

At the beginning of December, Wikidata items on individual scientific articles passed the 10 million mark. This figure contrasts with the state of play in early summer, when there were around half a million. In the big picture, Wikidata is now documenting the scientific literature at a rate that is about eight times as fast as papers are published. As 2017 ends, progress is quite evident.

Behind this achievement are a technical advance (fatameh), and bots that do the lifting. Much more than dry migration of metadata is potentially involved, however. If paper A cites paper B, both papers having an item, a link can be created on Wikidata, and the information presented to both human readers, and machines. This cross-linking is one of the most significant aspects of the scientific literature, and now a long-sought open version is rapidly being built up.

The effort for the lifting of copyright restrictions on citation data of this kind has had real momentum behind it during 2017. WikiCite and the I4OC have been pushing hard, with the result that on CrossRef over 50% of the citation data is open. Now the holdout publishers are being lobbied to release rights on citations.

But all that is just the beginning. Topics of papers are identified, authors disambiguated, with significant progress on the use of the four million ORCID IDs for researchers, and proposals formulated to identify methodology in a machine-readable way. P4510 on Wikidata has been introduced so that methodology can sit comfortably on items about papers.

More is on the way. OABot applies the unpaywall principle to Wikipedia referencing. It has been proposed that Wikidata could assist WorldCat in compiling the global history of book translation. Watch this space.

And make promoting #1lib1ref one of your New Year's resolutions. Happy holidays, all!

Links

WikidataCon: Giving more people more access to more knowledge, report by Peter Kraker of Open Knowledge Maps
This is a story of my knowledge adventure in New Zealand moths via Wikicommons, Wikipedia and Wikidata, @SiobhanLeachman
Wikidata and Arabic dialects, research paper, DOI: 10.1109/AICCSA.2017.115
c:Commons:British Library/Mechanical Curator collection/georeferencing status, Mechanical Curator project on Commons hits 50K maps milestone
Historical dataset on the provenance of Wikipedia text: Who wrote this?, by Tilman Bayer, WMF blogpost
"Anyone can edit", not everyone does: Wikipedia and the gender gap (PDF), journal paper, Heather Ford and Judy Wajcman
Alpha Zero’s "Alien" Chess Shows the Power, and the Peculiarity, of AI, MIT Technology Review, by Will Knight, December 8, 2017

To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see below.
Editor Charles Matthews, for ContentMine. Please leave feedback for him. Back numbers are here.
Reminder: WikiFactMine pages on Wikidata are at WD:WFM.

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) 14:54, 15 December 2017 (UTC)

Aarhus Protocol on Persistent Organic Pollutants vs. POP Air Pollution Protocol

I am unsure whether or not these two articles are about the same subject. Does anyone have more insight? --Leyo 14:47, 3 December 2017 (UTC)

→ Talk:Aarhus Protocol on Persistent Organic Pollutants#Merger proposal --Leyo 22:06, 16 December 2017 (UTC)

C2-Symmetric ligands

I realized that we have no article or category on C₂-symmetric ligands. Might be something worth doing (before the homeworkers).--Smokefoot (talk) 23:40, 21 December 2017 (UTC)

It seems awfully precise for a wikipedia article of it's own. Would you then create separate articles for C₄-symmetric ligands and every other point group? EvilxFish (talk) 12:22, 22 December 2017 (UTC)

EvilxFish, good point, but it is only C₂ that are special . The topic is pretty specialized, but there is intense interest, and even some real apps. An initial article might end up being just a hefty redirect, basically a definition and then pointing readers to many articles as Osprey indicates below. --Smokefoot (talk) 03:50, 23 December 2017 (UTC)

They are an important class, I would consider Whitesell's review on them to be seminal doi:10.1021/cr00097a012. The idea is mentioned with varying levels of detail at chiral ligand and lewis acid catalysis. I also (wrongly) added info about it at bisoxazoline ligand back when I first started - but the info doesn't belong there. I have thought about trying to collate/improve coverage at chiral ligand but I have issues with the page - we don't have an article on asymmetric catalysis - but to my mind a discussion of chiral ligands and asymmetric catalysis is indivisible. Sorting that out is a much bigger job and one that I keep putting off. --Project Osprey (talk) 02:15, 23 December 2017 (UTC)

OK, maybe I will try to create something short and sweet with that ref.--Smokefoot (talk) 03:50, 23 December 2017 (UTC)

Tethering

Would anyone like to have a look at the recently accepted article Tethered intramolecular (2+2) reactions? As I complete layman, I couldn't help but notice that there doesn't seem to be any article that properly explains the concept of tethering, even though the term occurs in quite a few articles. It is a concept of its own, right? There's a brief definition at Tether (cell biology), but that's too little and it's in the wrong place. – Uanfala (talk) 00:43, 29 December 2017 (UTC)

I don't see "tether" as a well-defined scientific concept. And there's only a very loose connection between the bacteriological and the chemical senses you mention. If I use a long rope to tie a goat to a fencepost, leaving it able to roam around within limits, I have tethered it — and this sense of "tether" is used metaphorically in various ways. Maproom (talk) 10:33, 29 December 2017 (UTC)

The article looks legit to me.. Pretty specialized but worthwhile. --Smokefoot (talk) 13:34, 29 December 2017 (UTC)

No, this is more Carolineneil stuff, the same content is duplicated in Intramolecular reaction. Suggest deleting the article, keep the Intramolecular reaction content. V8rik (talk) 15:45, 29 December 2017 (UTC)

I defer to V8rik, its more in his area. There is also some overlap with 2+2 Cycloaddition. --Smokefoot (talk) 16:13, 29 December 2017 (UTC)

Ah, my bad – I've missed the fact it was a duplicate. Thank you both for the feedback. Now, I've merged the two versions into Intramolecular reaction#Tethered intramolecular 2+2 reactions. Is this ultimately the best place for this text, or should it be moved to 2+2 Cycloaddition? Back on the question of tethers, the Intramolecular reaction#Molecular tethers seems to define it as a concept, is that enough to create the redirect Tether (chemistry) pointing there, or is the term generally used, as Maproom suggested, in vague ways that are not covered by that section? – Uanfala (talk) 17:24, 29 December 2017 (UTC)

navbox Stereochemistry

Could someone create a navbox Stereochemistry or a navbox Descriptor (Chemistry)? All the descriptors like Cis–trans isomerism, Geminal etc. (listed in the article Descriptor (Chemistry)) are for the moment difficult to find. Minihaa (talk) 13:14, 28 December 2017 (UTC)

Done, see {{Navbox stereochemistry}}. Mosty based on Descriptor (Chemistry) (copied a bit blindly, I am not very familiar with the topic). I think there might be improvements waiting: note when form is obsolete, refine descriptoins, order. -DePiep (talk) 15:40, 29 December 2017 (UTC)

Thank you so much for the swift processing. Great job! I am going to change it or ask you when it may be necessary. Thank you very much. Minihaa (talk) 21:53, 29 December 2017 (UTC)

Yet more incoming

Wikipedia:Wiki Ed/Western/Bio 3595 AdGen Wikipedia Project (Fall) is another set of articles being dropped onto Wikipedia. The topics, very biochemical, are not quite as bizarre as those from LSU, but again the instructor does not appear to have edited in Wikipedia and is counting on us to do his dirty work.--Smokefoot (talk) 01:21, 1 December 2017 (UTC)

You might want to cross-post this to the bio/pharma communities... Is it me or are we seeing more of this every year?--Project Osprey (talk) 08:42, 1 December 2017 (UTC)

One reason for proactively creating articles (and redirects) is to preempt these unsupervised student projects. Increasingly the weak classes are forced into writing articles that no one cares about (Environmental impact of silver nanoparticles). --Smokefoot (talk) 14:53, 1 December 2017 (UTC)

Not sure we can proactively cover all possible niche article titles... and even if we could I just wouldn't want to. A different proactive approach might be to write something for The Journal of Chemical Education about how to (and how not to) run these projects.--Project Osprey (talk) 16:15, 1 December 2017 (UTC)

The instructors probably do not read chemistry journals. So we write an article, the courses continue. We rant about their failure to follow our advice.

Part of the problem is that the so-called Wiki-Ed supervision/advice apparatus is broken. My guess is that the Wikipedia bureaucracy thinks that student involvement is a means of growing the number of editors. And for this bureaucracy, the number of editors = vitality. In reality, the decline in Wikipedia editor count may be partially a consequence of the low-hanging fruit/articles having been written, and only hard parts remain. And who wants to do the dirty work and revise photoredox catalysis? Not many.--Smokefoot (talk) 17:00, 1 December 2017 (UTC)

This class has been contributing heavily to Gene Wiki articles. While the quality of the contributions have varied considerably, many of the contributions have clearly been solid, good faith contributions. The main problem as I see it is the editing guidlines that the students were given. No where in the guidlines is it stated that secondary sources are preferred. The problem is especially acute in biomedical subjects because of the reproducibility crisis. To their credit, these students have responded constructively to {{Unreliable medical source}} templates. Boghog (talk) 17:50, 1 December 2017 (UTC)

The brochure is slick but not very practical. We need a one-page list of do's and donts. The parts of the system that need to be addressed are Wiki Ed, which appears not to pay attention @Ian (Wiki Ed): and the instructors. Without attention from WikiEd, we are stuck with crappy articles. It has been like this for years. And the sour part is that WikeEd group is probably congratulating themselves on what a fine job they are doing. The other thing is that if the instructors are not involved, we are doubly screwed because we few need to do the cleanup. It is this situation that really makes me despair about the whole project. One consequence is that I have taken MOFs and nano-anything off my watch list because these articles are just overwhelmed with over-specialized accretions and so few editors curate these things. --Smokefoot (talk) 18:16, 1 December 2017 (UTC)

Hi all. I know that my colleagues are looking into the issues you've brought up with this class. It's not always evident on-wiki because often the best way to ensure students comply with instructions is to talk directly with their instructor. The students received not just the Editing Wikipedia handout but also this subject-specific handout chemistry students receive, which does address the preference for secondary sources. Classes which indicate they will work on classes covered by WP:MEDRS also go through a dedicated training module. We're in the midst of the busiest time for student writing, so I apologize that the time it takes to resolve an issue may be a little longer than during most of the rest of the year. --Ryan (Wiki Ed) (talk) 20:38, 1 December 2017 (UTC)

Editors in the chemistry project have been raising similar issues every semester for the past few years. Who cares if students can "edit Wikipedia" if their content is awful and their topics are poorly selected? Is the point to attract quality content or is the mission of Wiki Ed to inculcate this pool of forced labor? The evidence is that Wiki Ed, inadvertently perhaps, focuses on Wikipedia-as-a-brand vs Wikipedia-as-a-vehicle-for-knowledge.--Smokefoot (talk) 21:00, 1 December 2017 (UTC)

Hello @Ryan (Wiki Ed):. To be honest, I don't have a detailed understanding of what WikeEd does and I think for the purposes of this it would be good to know. What sort of influence or oversight do you have on these projects? Smokefoot is correct that the articles we currently get are often badly written and on topics that we just don't need (improper disposal of latex balloons and its environmental effects springs to mind). This is exacerbated by the fact that we usually discover that 20-30 such articles will have been created in the last week. Attempts to delete (and the vast majority are eventually deleted or merged) or edit any of these is often met with protests from students worried about their grades. Attempts to contact course supervisors are usually done in vain. It's embittering - and the experience seems to be a negative one for all parties.

On the plus side, that gives us plenty of room to improve. I think that selecting the correct new articles to create is key - its easier to write a well structured article on a well defined topic and that in turn makes it easier for us to curate. There is other low-hanging fruit, your subject-specific chemistry handout doesn't even mention this community or a good number of other things. Do course supervisors get similar handouts? If so there is likely much we could suggest that would help things run more successfully. --Project Osprey (talk) 23:21, 1 December 2017 (UTC)

@Project Osprey: Thanks. Some background: Wiki Education is a small non-profit with roots in the Education Program. Whereas WMF still runs the Global Education program everywhere other than the United States and Canada, Wiki Education works with institutions in those two countries. We talk with instructors to help them with assignment design, explain best practices, and watch for red flags (like a very large class, multiple sections each taught by a different TA, grading based on whether or not contributions "stick", only allowing a short period of time for contributions, not working on sandboxes first, etc.). We also develop resources to try to achieve our goals. The Dashboard is a tool we developed which generates an assignment timeline, links to resources, and structures the assignment according to steps/milestones. The Dashboard also contains interactive training modules, including multiple required and optional trainings for students and an orientation all instructors go through (basically "instructor training"). We update these resources pretty regularly in response to how they've worked and in response to feedback from both instructors and members of the Wikipedia community. We also have a variety of brochures, both for general editing/evaluation and subject-specific handouts like the chemistry handout I linked above. Finally, there are paid staff. A Classroom Program Manager talks with instructors throughout the process (but especially during the onboarding process), and Content Experts (like Ian) work with students and their content. As I mentioned above, it's the busiest time of year for them. All of this said, if you think that students having trouble would reliably receive help here it may be something we'd want to add next time we edit it. Likewise, if you have other specific feedback about that handout, you should always feel welcome to post it either at my talk page (or even WP:ENB).

Getting to some of the specifics of your comment:

We do often tell classes about WikiProjects. The reason we don't usually include them in materials like this is for a few reasons. The biggest reason is because if it's there, then students or instructors will assume rely on it. When it sparks a good conversation, it's very rewarding, but it's far from a sure thing that they will receive answers/help when so few WikiProjects are particularly active. That's a general answer, of course; I know this WikiProject is among the more active. That brings me to the next thing -- we want to, whenever possible, reduce rather than increase burden on the community. People in the community have voiced several, sometimes conflicting, perspectives on the extent to which they would like to see students post to talk pages, etc. Use of talk pages is a wikivirtue, in general, of course, but student comments could also get overwhelming if all sent to a particular on-wiki resource.

It seems like many of the issues are things worth discussing at a higher level than individual articles. You mentioned student protests about their grade. This is something that, similar to grading based on content that "sticks", we really don't like to see. You shouldn't have to deal with that. If you see a student argue using their grade as justification, please let us know at WP:ENB and we'll talk with their instructor.

You also mentioned article selection. I agree that's a significant variable in determining whether a student will be successful. Our Content Experts are long-time Wikipedians who understand best practices for article selection. Of course, we can't force anyone to follow our recommendations, but we can try really hard to show them the right way. I know that we're investigating, with regard to at least one of the classes above, if there was a way we could've presented our recommendations more convincingly at the outset such that these article selection issues wouldn't come up.

Thanks for your feedback and sorry for this long reply. :) --Ryan (Wiki Ed) (talk) 18:04, 2 December 2017 (UTC)

On the subject of topic selection, it would be good for the topics to be checked by a project before students spend time working on an unsuitable topic. Some of the classes pick good topics, but some others, particularly the one that writes about "environmental impact of ..." articles usually pick topics that lead to a synthesis. Graeme Bartlett (talk) 23:20, 2 December 2017 (UTC)

Well the process requires Wiki Ed to do something. But hey, they're "investigating". --Smokefoot (talk) 00:04, 3 December 2017 (UTC)

Keep student articles as drafts?

If this often bothers editors around here, is it a good idea to create these articles as drafts? Georginho (talk) 12:47, 3 December 2017 (UTC)

Great idea if it could be implemented. How to make that happen?--Smokefoot (talk) 21:39, 3 December 2017 (UTC)

The best is to change the process: 1) create a draft, 2) the draft is assessed by the supervisors in order to fix the grade, 3) the contributor can ask for publishing his/her draft into the main domain after assessment by community. The educational project has to be separated from the contribution to WP.

From our experience with the MOOC in WP:fr, most articles just need a small improvement after the reading of one skilled contributor. 130 drafts were reviewed into 3 weeks this year so this seems feasible if wikiprojects are involved from the beginning. Snipre (talk) 22:57, 3 December 2017 (UTC)

I think it is essential that we get across the idea that all student projects should be about creating drafts and not articles. As above all assessment can be done at the draft stage and then there can be collaboration on the article creation. I have been retired for a long time and no longer teach undergraduates. I would certainly have done it that way if I had students after wikipedia was created. --Bduke (Discussion) 02:53, 31 December 2017 (UTC)

Getting articles, not essays

The issue, at least as I see it, is essays. Supervisors are accustomed to setting essays and students are accustomed to writing them – if you tell a university student to write an article they will do you an essay, it’s their default format. This must be met head-on. Class assignments should explicitly state that one purpose of the assignment is that students should learn to write in an encyclopedic tone, and that they will be graded on this. This will help steer the students efforts but will only go so far, because if the titles they’re given to write about are naturally essays then I can see students defaulting to essay writing. What I mean by this is titles that can be generalised as ‘X about Y’

These are naturally essays, you’d start by writing an introduction and a conclusion is clearly needed somewhere and so before you know it you have an essay. Article selection is therefore key. I think distinct small molecules would be a good area to recommend:

There’s a large list of these in the waiting Wikipedia:Requested_articles/Natural_sciences/Chemistry#Chemical_compounds
They can be broken down into obvious sections (chembox, lead, synthesis, structure and properties, reactions etc) this disfavours essay writing, plus all students can be given the same guidance.
It still involves a good range of skills – primary references for chembox, reviews for the lead, planning, writing, making images etc (Required: prominent links to Wikipedia:Manual of Style/Chemistry)

I think pushing this with WikiEd might yield results - in my opinion anyway--Project Osprey (talk) 12:20, 7 December 2017 (UTC)

Agree 100%. There are already many articles that need creating. Galobtter (pingó mió) 12:43, 7 December 2017 (UTC)r

Recruit new editors for your project?

Happy new year! I've been building a tool to help WikiProjects identify and recruit new editors to join and contribute, and collaborated with some WikiProject organizers to make it better. We also wrote a Signpost article to introduce it to the entire Wikipedia community.

Right now, we are ready to make it available to more WikiProjects that need it, and I’d like to introduce it to your project! If you are interested in trying out our tool, feel free to sign up. Bobo.03 (talk) 19:49, 3 January 2018 (UTC)

@Bobo.03: A nice initiative this is! I'm sorry that at the moment I do not have time to dive into it. All the best, DePiep (talk) 08:24, 9 January 2018 (UTC)

Create equivalent to de:Vorlage:Alfa?

Would it be possible to create the equivalent to de:Vorlage:Alfa in the English Wikipedia? It would help with translations into English (when an identical form is chosen). Minihaa (talk) 22:40, 8 January 2018 (UTC)

It fomats a identifiers for database Alfa (example: L04911 for Adrenalin, example from de:doc).

I don't know that database, other people would have to support its inclusion in the infobox {{Chembox}} (talk). With this, I not that this enwiki probably will not use the full-template-input as dewiki does; we usually add a parameter to the {{Chembox}} (or pull it from Wikidata). -DePiep (talk) 00:14, 9 January 2018 (UTC)

I guess that Minihaa intends to use that template for refs only. --Leyo 01:07, 9 January 2018 (UTC)

Alfa is a commercial supplier. IMHO, what a commercial supplier tells to be properties or data for a compound is reliable for the material they sell, it is not necessarily reliable for the material itself (properties are dependent on grades and contaminants). --Dirk Beetstra ^{T C} 08:16, 9 January 2018 (UTC)

(ec). te Leyo. The dewiki template produces:

{{Alfa|L04911|Name=Adrenalin|Datum=9. Januar 2018}} →

Datenblatt Adrenalin bei AlfaAesar, abgerufen am 9. Januar 2018 (JavaScript erforderlich).

This could be a footnote-reference (it is not actually a source, is it?, not fit for ref tag). It is mainly an external link. On enwiki, these compound-based external links, for other id-numbers, are provided in {{Chembox}}, {{Infobox drug}}.

I don't think providing this template for inline usage (as footnote or ref), is good enough. And when in the infobox, this wiki works with parameters (like, |alfa=L04911 in Chembox Adrenalin). That is, if people want that alfa database linked. Does it add info? Isn't it a commercial site?

I must say, dewiki has similar templates to be used as input in the infobox:

|alfa = {{Alfa|L04911|Name=Adrenalin|Datum=9. Januar 2018}}. That is a nice system, but would take a large overhaul here. -DePiep (talk) 08:21, 9 January 2018 (UTC)

Just have a look, e.g. de:Borneole#cite_note-Alfa(-)B-3 or de:Geraniol#cite_note-ALFA-2. --Leyo 09:29, 9 January 2018 (UTC)

We have a related template in the form of Template:Sigma-Aldrich. I use this in chembox, to help reference hazard data from MSDS forms. --Project Osprey (talk) 09:31, 9 January 2018 (UTC)

Good example, saw ammonia. Inline ref then, not in-{{Chembox}} (like CAS Number does). Remaining question: do we want that EL to alfa site as a reference? - DePiep (talk) 09:55, 9 January 2018 (UTC)

To be honest I wouldn't use it. Sigma has a much larger catalogue that Alfa, so I would always go there first for MSDS data and I only ever use suppliers as sources for hazard data (it's the one thing they're good for). --Project Osprey (talk) 10:39, 9 January 2018 (UTC)

The supplier data is mostly not suitable as references, nor as 'identifiers', only as 'external links' as they provide sometimes a lot of detail (and MSDS, spectra). At the moment, I would indeed only use it in the MSDS-field in the chembox (though there are non-commercial (academic? Oxford stopped, right?) sources available .. ). Also for the cases where we need to link to e.g. the NMR or IR spectra, we could consider to use the Japanese SDBS for that (that number is a bit more an identifier). I do think that as strict external links (as in the 'external links' section) they fail our inclusion standards. They are commercial in nature, aimed at selling the product, all the information there can be included (though then should be sourced elsewhere, and most physical data is available from the aggregators like PubChem/DrugBank/ChemSpider/&c.).

Regarding de:Geraniol#cite_note-ALFA-2 - I am not sure whether that reference is a proper reference for the density .. I'd prefer a reviewed, academic source for that. I am sure that the density of Geraniol is available in the 'old books', including in the paper where they originally isolated it. I would use these data for quick data, but if for some reason I need proper data I would for sure not get it here.

In short, there is use for it, but limited. We could copy the templates and use where needed, I prefer that these things are template so we can easily adapt if external links change, or we want a different formatting. --Dirk Beetstra ^{T C} 10:32, 9 January 2018 (UTC)

If I understand this well: most if noty all data is on non-commercial sites too. Adding this would only be for "ease", and even that not in the {{Chembox}} identifiers section (say those who want all & everything in there ;-) ). In short, I propose to conclude, we are WP:NOTDIRECTORY nor WP:LINKFARM. In individual cases where it does add information or sourcing, a regular handcrafted ref/link can be typed. -DePiep (talk) 11:40, 9 January 2018 (UTC)

True, the handcrafted link where needed can be typed indeed .. but if it is template it is easier if once Alfa decides to change the format of their URL - then you don't need to edit all ## pages that have the link, you just change the template. --Dirk Beetstra ^{T C} 13:17, 9 January 2018 (UTC)

@Beetstra: Well, there is no reference for the density of geraniol in en-WP. Hence, you may decide what to prefer. You may pick another of the 741 de-WP articles using that template. ;-) --Leyo 13:24, 9 January 2018 (UTC)

@Leyo: There is, in a way, a reference in it, at the bottom of the chembox through Wikipedia:Chemical_infobox#References. Now I would agree that the material on en.wikipedia could be more directly referenced, but preferably to something that is not commercial. I guess that Geraniol is one of those compounds that will have quite some secondary (probably old papers) and tertiary references (CRC handbook?).

Just for fun: Alfa actually mentions the density to be 0.884 g/mL, which I would round to 0.88 g/mL, not 0.89 g/mL, the number that is listed on de.wikipedia (en.wikipedia lists 0.889 g/mL, I wonder where that discrepancy comes from); Alfa also sells water, e.g. reagent grade on https://www.alfa.com/en/catalog/036645/. The density they list is 1.000 g/mL (3 zeros!), but that is only true at 3.98 °C, not at 20°C (where it is 0.9970474 g/mL, which I would round to 1, 1.0, 1.00, and to 0.997, but not to 1.000). For the same material, Alfa lists a boiling point of 100 °C, whereas that probably should be 99.8°C. --Dirk Beetstra ^{T C} 13:46, 9 January 2018 (UTC)

I understand your concerns about the data quality and I fully agree that Alfa should not be used as a standard reference. However, when I translate an article Alfa is given as a reference in some cases. I do not have access to the CRC handbook. I could either leave the value unreferenced or reformat the link.

If the template would be translated it would save the translators the reformatting work in the first instance. Later on someone could go through all the articles with the template and substitute them with a proper reference. --Minihaa (talk) 14:02, 9 January 2018 (UTC)

I have no objections against the template (and can see the advantages), I have however reservations for its use, which is limited. --Dirk Beetstra ^{T C} 16:04, 9 January 2018 (UTC)

Question is: is it a RS? -DePiep (talk) 16:46, 9 January 2018 (UTC)

Facto Post – Issue 8 – 15 January 2018

Facto Post – Issue 8 – 15 January 2018

Metadata on the March

From the days of hard-copy liner notes on music albums, metadata have stood outside a piece or file, while adding to understanding of where it comes from, and some of what needs to be appreciated about its content. In the GLAM sector, the accumulation of accurate metadata for objects is key to the mission of an institution, and its presentation in cataloguing.

Today Wikipedia turns 17, with worlds still to conquer. Zooming out from the individual GLAM object to the ontology in which it is set, one such world becomes apparent: GLAMs use custom ontologies, and those introduce massive incompatibilities. From a recent article by sadads, we quote the observation that "vocabularies needed for many collections, topics and intellectual spaces defy the expectations of the larger professional communities." A job for the encyclopedist, certainly. But the data-minded Wikimedian has the advantages of Wikidata, starting with its multilingual data, and facility with aliases. The controlled vocabulary — sometimes referred to as a "thesaurus" as term of art — simplifies search: if a "spade" must be called that, rather than "shovel", it is easier to find all spade references. That control comes at a cost.

Case studies in that article show what can lie ahead. The schema crosswalk, in jargon, is a potential answer to the GLAM Babel of proliferating and expanding vocabularies. Even if you have no interest in Wikidata as such, simply vocabularies V and W, if both V and W are matched to Wikidata, then a "crosswalk" arises from term v in V to w in W, whenever v and w both match to the same item d in Wikidata.

For metadata mobility, match to Wikidata. It's apparently that simple: infrastructure requirements have turned out, so far, to be challenges that can be met.

Links

1lib1ref campaign starts today, see m:The Wikipedia Library/1Lib1Ref: also #1lib1ref introductory video by Felix Nartey
Funders should mandate open citations, article 9 January 2018 in Nature by David Shotton
From snowflake to avalanche: Possibilities of using free citation data in libraries, translation from the German original of Annette Klein, Mannheim University Library
outreach:GLAM/Newsletter/December 2017/Contents/WMF GLAM report
Why Mickey Mouse’s 1998 copyright extension probably won't happen again: Copyrights from the 1920s will start expiring next year if Congress doesn't act, Timothy B. Lee, 8 January 2018, Arstechnica

To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see below.
Editor Charles Matthews, for ContentMine. Please leave feedback for him. Back numbers are here.
Reminder: WikiFactMine pages on Wikidata are at WD:WFM.

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) 12:38, 15 January 2018 (UTC)

Redirecting chemical name to acronym

More eyes from the chemistry community would be helpful at this move discussion at Talk:Dichlorodiphenyltrichloroethane#Requested_move_24_January_2018 asking it be moved to an acronym for a title instead (the proposed move target of DDT currently redirects the page). There has been some discussion trying to justify the move saying TNT is now a precedent after it was also moved from its chemical name to acronym even though there was very little participation in that TNT move discussion. It would be great to get more eyes in this compared to the TNT move discussion. Kingofaces43 (talk) 16:02, 26 January 2018 (UTC)

And just so it's clear, I'm not trying to hold support/oppose votes in different lights in this notification. I point out the TNT discussion because it had little participation, and it seems to be a different direction for chemical article names that should have attention from the wider chemistry community to determine which way we eventually decide to go. Maybe folks here want to go the acronym route, or maybe they don't, but it's something that's reached wider implications for this project. Kingofaces43 (talk) 17:06, 26 January 2018 (UTC)

Yes, is how I have read it. -DePiep (talk) 17:18, 26 January 2018 (UTC)

Similarly, there is also an ongoing discussion at Talk:Tetrahydrocannabinol requesting the move of Tetrahydrocannabinol to THC. ChemNerd (talk) 19:55, 26 January 2018 (UTC)

Nonivamide

The infobox flags up verification issues, but all the information in it is correct.--139.133.116.11 (talk) 22:17, 27 January 2018 (UTC)

{{IUPAC_spelling_US}} etc. merge proposal

See this TfD. - DePiep (talk) 13:24, 28 January 2018 (UTC)

Thanks, I don't think I could ever spell sulphur as sulfur, it just seems so wrong. :) EvilxFish (talk) 20:03, 28 January 2018 (UTC)

You have to, because else you will burn in hellish fire and brimstone, IUPAC-spelled as your eternal punishment! - DePiep (talk) 20:23, 28 January 2018 (UTC)

Facto Post – Issue 9 – 5 February 2018

Facto Post – Issue 9 – 5 February 2018

m:Grants:Project/ScienceSource is the new ContentMine proposal: please take a look.

Wikidata as Hub

One way of looking at Wikidata relates it to the semantic web concept, around for about as long as Wikipedia, and realised in dozens of distributed Web institutions. It sees Wikidata as supplying central, encyclopedic coverage of linked structured data, and looks ahead to greater support for "federated queries" that draw together information from all parts of the emerging network of websites.

Another perspective might be likened to a photographic negative of that one: Wikidata as an already-functioning Web hub. Over half of its properties are identifiers on other websites. These are Wikidata's "external links", to use Wikipedia terminology: one type for the DOI of a publication, another for the VIAF page of an author, with thousands more such. Wikidata links out to sites that are not nominally part of the semantic web, effectively drawing them into a larger system. The crosswalk possibilities of the systematic construction of these links was covered in Issue 8.

Wikipedia:External links speaks of them as kept "minimal, meritable, and directly relevant to the article." Here Wikidata finds more of a function. On viaf.org one can type a VIAF author identifier into the search box, and find the author page. The Wikidata Resolver tool, these days including Open Street Map, Scholia etc., allows this kind of lookup. The hub tool by maxlath takes a major step further, allowing both lookup and crosswalk to be encoded in a single URL.

Links

What galleries, libraries, archives, and museums can teach us about multimedia metadata on Wikimedia Commons, Wikimedia Foundation blogpost, 29 January 2018, by Jonathan Morgan and Sandra Fauconnier
m:The Wikipedia Library/1Lib1Ref/Connect, 2018 institutional participation in the #1lib1ref campaign
Newspeak House queries, created at 3 February 2018 event in London led by Magnus Manske
Cochrane–Wikipedia Initiative, Wikipedia Signpost special report 5 February 2018, by JenOttowa
What is the Last Question?, 5 February 2018

To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see below.
Editor Charles Matthews, for ContentMine. Please leave feedback for him. Back numbers are here.
Reminder: WikiFactMine pages on Wikidata are at WD:WFM.

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) 11:50, 5 February 2018 (UTC)

Proposing a rename

Hi all please consider chipping in to the discussion here. The article is a bit of a mess and does need attention as well. Lot's of things to fix :) EvilxFish (talk) 14:34, 7 February 2018 (UTC)

Edison–Lalande cell

Edison–Lalande cell currently covers three different cells, only one of them the Edison cell. Is there a better name for this article? Perhaps one based on cell chemistry? -- 67.70.34.54 (talk) 05:58, 23 February 2018 (UTC)

Latex balloon additives

Could someone add something about the additives (plasticisers, colourants, etc.) used in latex balloons, to Balloon, please? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 19:06, 26 February 2018 (UTC)

The possibilities there are extensive to say the least - and will vary according to the brand and colour of balloon.--Project Osprey (talk) 20:26, 26 February 2018 (UTC)

Tetranitratoxycarbon

Can someone please assist with the article above. The structure in the chembox is clearly wrong but it matches the SMILES provided. I can't get into the citing paper to check. There's a cute story behind it but I'm not sure this compound meets our normal requirements for notability. --Project Osprey (talk) 13:14, 27 February 2018 (UTC)

Cute stories are difficult to remove from Wikipedia. --Smokefoot (talk) 13:39, 27 February 2018 (UTC)

The structure is correct. It is certainly weird, and that is why this was not studied before. Given that several independent writers have covered it, it counts as notable. If this was the astronomy project, we would have rated this as bottom importance, ie something that is popular, but of no relevance to serious study. Should we add bottom importance to chemicals project? Graeme Bartlett (talk) 01:23, 28 February 2018 (UTC)

Is there any precedent for any tricyclic compound of the type RC(μ-O)₃N? If there is none, maybe we should try to remove it.--Smokefoot (talk) 02:32, 28 February 2018 (UTC)

The source article is calling this structure "nitrato-O,O,O-" or "nitratoxycarbon", but from the article it sounds like it has never been made with carbon. Wouldn't this be bicyclic? Anyway does a heterocycle with NOCO in a ring exist even? (2,4-dioxazetidine) So far I can only find one mention of nitrato-O,O bonding with the same atom if it is uranium. There appears to be no precedent for RC(μ-O)₃N, before this topic. But there are now three computational chemistry papers on the topic. Normally I would say that chemicals that are only known through a computation are not important enough for articles here. But in this case we have WP:GNG. Graeme Bartlett (talk) 03:03, 28 February 2018 (UTC)

For simple (one-ring) 2,4-dioxazetidine analogs that have some preparative reference, I see a bunch of "nitro compound as a bidentate ligand" to various d-block and f-block metals. As for main-group elements for the fourth atom of the ring, I see one example with bismuth (CAS# 1246287-63-7; see doi:10.1016/j.jhazmat.2009.11.021), and a bunch with nitrogen (ONON ring; a 1,3,2,4-dioxadiazetidine). Those include some bicyclics, but only where the third link between the nitrogens is two carbons (bicyclo[2.1.1]--nothing as small as a bicyclo[1.1.1] system. DMacks (talk) 04:30, 28 February 2018 (UTC)

It has a CAS No. CAS also lists the parent group (1400867-98-2) and there are a few similar species too, with 2N's and no C or 2C's and no N. All with a trigonal pyramidal structure and all purely theoretical. Having an article on something which doesn't exist bothers me. We do already have some hypothetical structures at Category:Hypothetical_chemical_compounds but surely WP:CRYSTALBALL applies here, we have no idea what the properties of a "nitratoxycarbon" compound might be - well, other than it being explosively unstable. --Project Osprey (talk) 09:50, 28 February 2018 (UTC)

I vote delete the article. Literally kids stuff.--Smokefoot (talk) 14:51, 28 February 2018 (UTC)

As Graeme Bartlett mentioned above, several independent writers in the lay press (I've just added a citation from HuffPost) have covered the prediction story of this molecule (which is more than can be said about, well, a lot of molecules). Despite not being well studied from a scientific perspective, I don't think that precludes inclusion of the article under the general notability guidelines. I would tentatively vote keep. ―Biochemistry🙴❤ 20:15, 28 February 2018 (UTC)

I'll go for a reluctant keep. If the structure were not suggested by a child, this would not have been notable. But it was, and so this compound got enough coverage from the lay press to satisfy WP:GNG (though I agree with Graeme Bartlett's idea of calling this bottom-importance). Double sharp (talk) 15:15, 3 March 2018 (UTC)

The term crystallogens for group 14: a case of citogenesis?

I am worried that this and its present existence in the literature may be a case of citogenesis, especially since I would then have unwittingly helped to push it forward through a combination of assuming a bit too much good faith and not being able to easily search the literature back in 2012 when I first noticed it and added it as an alternative though non-IUPAC-approved trivial name for the group. From the talk page:

I am a bit worried about this term (used to mean chemical elements in group 14 of the periodic table), most especially since I appear to have unwittingly gotten involved in its chain of transmission via assuming a little too much good faith. The article on group 14 was created on French Wikipedia by an anonymous IP in January 2006 with the title cristallogène, which translates indeed to crystallogen, as created on English Wiktionary by SemperBlotto (then already an established editor, and after all previously an industrial chemist) in June 2012. I added it as a redirect that September, assuming that there were references for it elsewhere that were not online; on that basis I also added it to this illustration of trivial names for groups in February 2013, together with icosagen which did indeed have a real reference (Greenwood and Earnshaw, 2nd edition, p. 227). However, I am now increasingly doubtful that such references ever existed: the one source I can find predating 2012 for it is a single patent from 2009–2010 (and, this postdating 2006, and having an organisation with a French name as an assignee, this may after all be traced back to the French entry).
Now, on the other hand, you will find lots and lots of references to this term in a multitude of reliable sources, for example:

Micro Energy Harvesting (2015), published by Wiley-VCH and referencing "Properties of Crystallogens (group 14)" on p. 106;

this paper (2015): "At this temperature, crystallogen sulfides (ie sulfur with element of the carbon group) are quite volatile";

this paper (2014): "More recently, the carbon atom substitution was pushed further and the next crystallogen element, germanium, attracted attention..."

this paper (2013): "where A is larger alkaline earth or rare earth cations, B is smaller crystallogen or pnictogen..."

this paper (2015): "Silicon belongs to the crystallogen family and is the most abundant element in the earth's crust after oxygen..."

...and yet more courtesy of Google Scholar.
I think it's too late to do anything now about this; for better or worse, even if crystallogens didn't use to mean it, it now really does mean "the elements of group 14". And it did fill what was previously an odd lexical gap (the names pnictogens, chalcogens, and halogens for groups 15, 16, and 17 are IUPAC-approved, and Greenwood and Earnshaw lists the proposed name icosagens for group 13 on p. 227; adamantogens for group 14, listed by W. B. Jensen, never seems to have gotten any following), so evidently chemists now feel the need for such a term. In this sense this is a rather benign example of citogenesis (if it is one, which seems to be rather likely), similar to the numbering of video game generations, as it filled a gap and was found useful by reliable sources (furthermore, it is etymologically sound). Still, it violated WP:NOR and I regret having been part of its progress (in my defense, not then knowing that it was original research). This having been nearly six years ago, I think I've quite painfully learned my lesson to shoot first and ask questions later when it comes to uncited and not obviously citable material. m(_ _)m
— User:Double sharp 14:36, 2 March 2018 (UTC)

(I have also informed Wikipedia:WikiProject Elements about this.) I might add that I think I might have been led into this by misunderstanding Sandbh's comment at Wikipedia talk:WikiProject Elements/Archive 13#Boron and carbon groups as indicating that sources existed for all three of the terms icosagens, crystallogens, and aerogens:

I have seen Greenwood & Earnshaw make mention of icosagens for group 13, in reference to the frequency of icosahedral structures in this group. Crystallogens for group 14 is beautiful. There was a suggestion in the 1960s to refer to the noble gases as aerogens.
— User:Sandbh 00:28, 15 September 2012 (UTC)

I am not sure what should be done about this matter, which I am very sorry to have been misled by, along I presume with SemperBlotto and the entire French Wikipedia chemistry community (French Wikipedia to this day still has lines like "Le carbone est la tête de file du groupe des cristallogènes" at fr:Carbone). It seems to have gotten into the literature mostly because "carbon group" is about as awful as "nitrogen group" for pnictogen (what is that, some kind of functional group, as Smokefoot said at Talk:Pnictogen#Requested move 2), and so the term filled a gap (Jensen's suggested adamantogen only really references carbon and was never taken up by anybody AFAIK). I think it might be fair to still mention it while making it clear that it is (1) a rare term and (2) not approved by IUPAC; we do (2) now but perhaps do not make (1) clear enough. If this was any earlier, before it seeped into the literature, I would support removing it entirely; but I think it's almost certainly too late for that. I am not sure if it's possible or even advisable to try to get rid of it; after all, both pnictogen and chalcogen were also sound terms etymologically that were made up by one chemist – Anton Eduard van Arkel in 1952–3 and Werner Fischer in 1932 respectively – and then taken up by others. The old IUPAC-suggested names for groups III, IV, and, triels, tetrels, and pentels, may thus all be doomed like how pnictogen has ousted pentels. Double sharp (talk) 10:36, 3 March 2018 (UTC)

P.S. Well, maybe I spoke too soon. There are only 6 pages of results in Google Scholar for crystallogen, and many of them appear in the legitimate terms crystallogenic or crystallogenesis, so that the huge amount we see for crystallogens is actually not that bad. The term crystallogen does seem to exist now in more of a way than the coinages adamantogen (W. B. Jensen) or merylide (W. C. Fernelius) never did, and admittedly pnictogen also had not that much usage from 1960 to 1970 (2 pages of results in Google Scholar). We might be able to nip this in the bud by de-accenting crystallogen and icosagen as trivial names (while they exist and are unambiguous, they are really rare). We can put them of course in "Naming" sections of the boron group and carbon group articles with citations but note that they are not official and not really used in the real world (I'd be more comfortable with removing crystallogen entirely, but since it has more use than adamantogen and merylide which really did exist in the literature I think we might be forced to give it a brief mention). Comments? Double sharp (talk) 17:03, 3 March 2018 (UTC)

OK, I have quickly gone through and added a mention that volatile metals meaning group 12 specifically, icosagens meaning group 13 specifically, and crystallogens meaning group 14 specifically are really rare. I will clarify the situation further on the articles tomorrow when I have more time. Double sharp (talk) 17:10, 3 March 2018 (UTC)

Aromatic acid and Category:Aromatic acids and Template:Aromatic acids

Most of phenols are acids. Most of them are weak acids. However, trinitrophenol is a strong acid. Sharouser (talk) 13:48, 8 March 2018 (UTC)

We need to set up criterias for categorization. Sharouser (talk) 13:51, 8 March 2018 (UTC)

Phenol has a pKa ~10 meaning that it not acidic in the normal sense, its derivatives have a wide range of pka's. To be honest I don't like the category, it seems WP:NONDEF to me. --Project Osprey (talk) 14:14, 8 March 2018 (UTC)

Picric acid is not a strong acid. The content of the aromatic acids category appears to be aromatic carboxylic acids, so perhaps the category should be renamed. This would also make for clear categorization. EdChem (talk) 14:20, 8 March 2018 (UTC)

Britannica says 'Aromatic acids include compounds that contain a COOH group bonded to an aromatic ring.' So they don't even call something an aromatic acid unless it is carboxylic. That's also the definition used (without reference) in our article at aromatic acid. So phenol and picric acid aren't aromatic acids by this criterion. If there are no non-carboxylic aromatic acids (according to normal usage) then maybe the category name can stay the same. EdJohnston (talk) 16:01, 8 March 2018 (UTC)

I would argue that tosylic acid is an aromatic acid, but it is not an aromatic carboxylic acid. As the OP noted, picric acid is also aromatic and with significant acidity. As for the Britannica definition, it's flawed if interpreted as EdJohnston is. According to the definition, "aromatic acids include" those with a direct carboxyl group (like benzoic acid), but what about indirect connections like cinnamic acid? The wording also allows for aromatic acids that don't include a carboxyl group. The OP is correct that "aromatic acids" is ill-defined. EdChem (talk) 16:17, 8 March 2018 (UTC)

So the definition could be as broad as "compounds with an aromatic group and a pka <7"? Categories are supposed to be useful and that seems very arbitrary. It's possible that this is a general term used in some other discipline (biochem?) but if not should it be deleted? — Preceding unsigned comment added by Project Osprey (talk • contribs)

In my chemical dictionary it calls some of these "carboxylic acids of aromatic series" which is a worse name, but we could make a category "category:aromatic carboxylic acids" instead, which is better defined. "category:Aromatic sulfonic acids" would cover tosylic acid. Graeme Bartlett (talk) 22:20, 8 March 2018 (UTC)

I agree with Project Osprey that a definition as broad as aromatic + acidic is unhelpful but it also appears to me to match the name, which is why I suggested renaming the category to Category:Aromatic carboxylic acids – that's pretty much what it contains anyway. Yes, Graeme Bartlett, a Category:Aromatic sulfonic acids would be a potential new category for articles like benzenesulfonic acid and tosylic acid... but do we need to categorise aromatic substances with chemically-significant acidity that aren't carboxylic or sulfonic acids like picric acid. 2-Naphthol has a pK_a of 9.51 and a solubility of 0.74 g L⁻¹ in water, so a pH of a saturated solution would be about 5.9 – is that acidic enough to warrant being in some category of intersecting acidity and aromaticity, and if so, where is the line drawn? Would we need a Category:Aromatic quaternary ammonium ions for the many pharmaceuticals that are stabilised as hydrochloride and similar salts? The cyclopentadienyl anion is basic and aromatic, should there be a general aromatic bases category to sit alongside Category:Aromatic amines? I believe the OP is correct that the present Category:Aromatic acids is ambiguous in scope but whatever resolution is reached will have flow-on considerations that also should be addressed. EdChem (talk) 22:54, 8 March 2018 (UTC)

We should split history of Template:Extended periodic table (by Fricke, 52 columns, large cells)

Since September 2017, this template represents 54 columns version of Fricke table.

Template:Extended periodic table (by Fricke, 52 columns, large cells) and Template:Extended periodic table (by Fricke, 54 columns, large cells) should be splitted. — Preceding unsigned comment added by Sharouser (talk • contribs) 07:21, 10 March 2018 (UTC)

Templates in other wikipedias also should be moved to appropriate names. --Sharouser (talk)07:25, 10 March 2018 (UTC)

The table has "53 columns" with a chemical element cell (bottom row has elements 119–172). This number is used to describe the graphical form, not its scientific claim BTW. Double sharp, can you confirm that the number has changed? - DePiep (talk) 09:26, 10 March 2018 (UTC)

@DePiep: It is indeed 54 columns (119–172), and it no longer shows Fricke's version (which is 52 columns) but Nefedov's (see this paper by Nefedov et al. covering elements 119 to 164). I have moved it to Template:Extended periodic table (by Nefedov, 54 columns, large cells). Double sharp (talk) 10:13, 10 March 2018 (UTC)

Glad you can count! -DePiep (talk) 10:20, 10 March 2018 (UTC)

@DePiep, EdChem, and Double sharp: Page moving in other wikis and splitting of history are not finished. --Sharouser (talk) 11:16, 10 March 2018 (UTC)

Why should history be split? It still is an Extended periodic table. And: other wiki's should maintain themselves IMO. - DePiep (talk) 11:18, 10 March 2018 (UTC)

Because we need a template about Fricke template. [4] I think that we shuld split this history to three article.--Sharouser (talk) 11:34, 10 March 2018 (UTC)

I moved the template in srwiki. The template in Kowiki should be renamed too --Sharouser (talk) 11:34, 10 March 2018 (UTC)

I can hardly move it myself on kowiki, as I am not autoconfirmed there, I do not understand Korean, and I have no idea what "Nefedov" should transliterate to in Korean (though Google translate suggests 네프도프 nepeudopeu). Double sharp (talk) 12:22, 10 March 2018 (UTC)

"Nefedov" should transliterate to "네페도프" in Korean. — Preceding unsigned comment added by 223.62.163.204 (talk) 16:02, 10 March 2018 (UTC)

Thank you very much for the correct transliteration and your moving the page! As previously mentioned, I don't understand Korean and relying on Google Translate can be rather iffy. ^_^ Double sharp (talk) 17:02, 10 March 2018 (UTC)

Facto Post – Issue 10 – 12 March 2018

Facto Post – Issue 10 – 12 March 2018

Milestone for mix'n'match

Around the time in February when Wikidata clicked past item Q50000000, another milestone was reached: the mix'n'match tool uploaded its 1000th dataset. Concisely defined by its author, Magnus Manske, it works "to match entries in external catalogs to Wikidata". The total number of entries is now well into eight figures, and more are constantly being added: a couple of new catalogs each day is normal.

Since the end of 2013, mix'n'match has gradually come to play a significant part in adding statements to Wikidata. Particularly in areas with the flavour of digital humanities, but datasets can of course be about practically anything. There is a catalog on skyscrapers, and two on spiders.

These days mix'n'match can be used in numerous modes, from the relaxed gamified click through a catalog looking for matches, with prompts, to the fantastically useful and often demanding search across all catalogs. I'll type that again: you can search 1000+ datasets from the simple box at the top right. The drop-down menu top left offers "creation candidates", Magnus's personal favourite. m:Mix'n'match/Manual for more.

For the Wikidatan, a key point is that these matches, however carried out, add statements to Wikidata if, and naturally only if, there is a Wikidata property associated with the catalog. For everyone, however, the hands-on experience of deciding of what is a good match is an education, in a scholarly area, biographical catalogs being particularly fraught. Underpinning recent rapid progress is an open infrastructure for scraping and uploading.

Congratulations to Magnus, our data Stakhanovite!

Links

Wikipedia goes 3D allowing users to upload .STLs for digital reference, Beau Jackson for 3dprintingindustry.com, February 22 2018
WikiCite report (video)
Formal publication and announcement of ISBN citation dataset, see Twitter post, February 23 2018
Plotting the Course Through Charted Waters, workshop on data visualization literacy from Mikhail Popov, Wikimedia Foundation
Using Wikidata to build an authority list of Holocaust-era ghettos, Nancy Cooey, United States Holocaust Memorial Museum, February 12 2018
Why Should You Learn SPARQL? Wikidata! Mark Longair, blogpost November 29 2017
Back to the future: Does graph database success hang on query language?, George Anadiotis for Big on Data, March 5 2018

To subscribe to Facto Post go to Wikipedia:Facto Post mailing list. For the ways to unsubscribe, see below.
Editor Charles Matthews, for ContentMine. Please leave feedback for him. Back numbers are here.
Reminder: WikiFactMine pages on Wikidata are at WD:WFM.

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) 12:26, 12 March 2018 (UTC)

Question about sources

I have found that some manufacturers and suppliers provide information that may not be in a chem article. What is the guideline or policy on using these sources? Best Regards, Barbara ✐ ✉ 11:23, 23 March 2018 (UTC)

Wikipedia talk:WikiProject Chemistry/Archive 44

Typography of primes

Accessibility

Ball-and-stick model

Class projects again

Disambiguation links on pages tagged by this wikiproject

WP:AALERTS need some help on Community Wishlist Survey

Periodic table scheduled for TFA

Nonsense article?

Talk:Unstable molecules

Facto Post – Issue 7 – 15 December 2017

A new bibliographical landscape

Links

Aarhus Protocol on Persistent Organic Pollutants vs. POP Air Pollution Protocol

C2-Symmetric ligands

Tethering

navbox Stereochemistry

Yet more incoming

Keep student articles as drafts?

Getting articles, not essays

Similar problem with Wikidata

Recruit new editors for your project?

Create equivalent to de:Vorlage:Alfa?

Facto Post – Issue 8 – 15 January 2018

Metadata on the March

Links

Redirecting chemical name to acronym

Nonivamide

{{IUPAC_spelling_US}} etc. merge proposal

Facto Post – Issue 9 – 5 February 2018

Wikidata as Hub

Links

Proposing a rename

Edison–Lalande cell

Latex balloon additives

Tetranitratoxycarbon

The term crystallogens for group 14: a case of citogenesis?

Aromatic acid and Category:Aromatic acids and Template:Aromatic acids

We should split history of Template:Extended periodic table (by Fricke, 52 columns, large cells)

Facto Post – Issue 10 – 12 March 2018

Milestone for mix'n'match

Links

Question about sources

Navigation menu

Search