Wikipedia talk:WikiProject Chemicals

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WikiProject Chemicals (Rated NA-class)
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Actual wikiproject info: statistics and alerts[edit]

The worklist shows the actual work to be done to achieve the goals of the Chemicals wikiproject. The choice of important compounds articles to work on has been finalized in an earlier stage of the wikiproject (around mid 2005), and no further articles are added, although we remain open for strong suggestions on this talkpage. The work these days focuses on improving the articles, from Chem Stub all the way to Chem A-Class articles. The table below shows that progress.

Worklist historical status
2005 2006 2007 2008 2009
 
Grade
Jun Oct May Oct Mar Oct Feb Aug Apr Dec
A-Class 29 26 32 32 33 25 25 23 18 18
B-Class 71 84 101 130 148 156 158 180 185 188
Start 112 131 199 190 174 174 180 153 160 161
Stub 97 130 46 29 27 27 19 26 19 18
unclassified 76 - - - - - - - - -
Total 385 371 378 381 382 382 382 382 382 382
percentage
Chem Start
55.1 65.0 87.8 92.3 92.9 92.9 95.0 94.0 95.0 95.3
weighted
progress, %
42.2 50.4 57.8 60.8 62.2 61.7 62.4 63.1 63.2 63.9


The percentage ≥ Chem Start was indicative of the initial effort. Now that we are progressing to more advanced progress, the weighted progress indicator is used, calculated as (Unclass*0 + Stub*1 + Start*2 + B-Class*3 + A-Class*4) / (Articles*4).



For the statistics for all chemicals, as registered by the bot, also see complete list

Article alerts
Articles for deletion
Proposed deletions
Categories for discussion
Templates for discussion
Featured article candidates
Requests for comments
Requested moves

FAC nomination of β-hydroxy β-methylbutyric acid - need feedback on the article's "Chemistry" section[edit]

Would anyone here be willing to do a review of the "Chemistry" section of β-hydroxy β-methylbutyric acid at its FAC nomination? One reviewer there (Nergaal) suggested that a chemist or someone with a strong chemistry background needs to look at and review that section. I'd really appreciate it if one of you takes on a review at the FAC nomination or even just offers some constructive, actionable feedback of the article's chemistry section. Seppi333 (Insert ) 22:07, 9 September 2016 (UTC)

MP/BP of β-Hydroxy β-methylbutyric acid[edit]

I've got a quick question about the melting point of β-Hydroxy β-methylbutyric acid (aka 3-Hydroxyisovaleric acid / β-Hydroxyisovaleric acid). I've found 3 sources that list different MPs and BPs for the compound:

Of these sources, only chemspider cites another source; hence, I assume the BP of 302.808 °C @ 760 mmHg is correct, but I'm still not really sure which MP to use. I was wondering if any of you knew of any database sources that corroborate the MP values (the only databases that I've checked are the ones currently listed in the article's drugbox); if not, should I just forego adding a MP to the drugbox?

Note that while the name listed in the compound heading/title differs with each source, they all list the same and CAS RN (625-08-1 ) and include the names from the other monographs as synonyms.
@Edgar181: You responded to a similar concern which was raised at Talk:Beta-Hydroxy_beta-methylbutyric_acid/Archive_1#Melting_point a while back, so I figured I'd ping you in the event that you have any further thoughts about this.

Seppi333 (Insert ) 19:11, 10 August 2016 (UTC)

Not to address your request for information on the m.p., but I will say that quoting the b.p. is semi-useless or maybe worse. Such compounds (beta-hydroxy acids) cannot be distilled, they just wipe out. A lot of sources quote calculated b.p.'s, but I dont know if these numbers have any significance in describing the compound, and in fact almost propagate the false ideas. Maybe I am off base, in which case others might help illuminate me. --Smokefoot (talk) 07:26, 11 August 2016 (UTC)
Smokefoot makes a good point. The 303 °C boiling point is not real - the compound will almost surely decompose well below temperature. Chemspider reports the experimental boiling point as "128 deg C / 7 mm (302.808 °C / 760 mmHg)". What this means is that it was experimentally determined to be 128 °C at reduced pressure, 7 mmHg. This can be extrapolated to estimate a boiling point at atmospheric pressure, 760 mmHg. But these kinds of estimates are not always very accurate and are have little real world meaning if the compound decomposes below that temperature anyway. It would be best to report just the experimental value (128 °C at 7 mmHg). With contradictory melting points, I'm not sure what is best to do. Maybe list multiple values with their references and let the reader decide what it means. Maybe just leave it out unless someone can find a reliable primary source experimental report rather than a database listing that might be erroneous and perpetuated from one database to another. For what it's worth, the source that I trust most, Chemical Abstracts, gives a mp value of "<-32 °C" with a reference that says, "PhysProp data were obtained from Syracuse Research Corporation of Syracuse, New York (US)". -- Ed (Edgar181) 20:28, 11 August 2016 (UTC)
Ah, I didn't realize the 720 mmHg value was extrapolated from the BP @ 7 mmHg. Thanks for clarifying that; I'll tweak the BP in the infobox accordingly. I noticed that ChemSpider also states "MP (exp database): <-32 deg C" in the Predicted - EPIsuite tab under the Properties tab, so I suppose I'll add that to the drugbox.
I appreciate the assistance with resolving this. Seppi333 (Insert ) 23:25, 11 August 2016 (UTC)
Addressed issue with images
Images

Would anyone be willing to redraw File:Calcium hydroxymethylbutyrate skeletal.svg and File:Hydroxymethylbutyric acid.png in svg so that the lines in these diagrams and the placement of the hydroxy group are consistent with how it's drawn in File:HMB synthesis.svg? I nominated this article at FAC so I figured it'd be best if the structure diagrams for HMB were uniform throughout the article. Seppi333 (Insert ) 00:23, 20 August 2016 (UTC)

Nevermind. I ended up extracting File:Beta-Hydroxy beta-methylbutyric acid.svg and File:Beta-Hydroxy beta-methylbutyrate.svg from File:HMB synthesis.svg. Seppi333 (Insert ) 23:44, 20 August 2016 (UTC)

Template:Piperazines[edit]

Template:Piperazines has been nominated for deletion. WikiProject Chemicals participants may be interested in contributing to the discussion at Wikipedia:Templates_for_discussion/Log/2016_August_29#Template:Piperazines. -- Ed (Edgar181) 19:01, 30 August 2016 (UTC)

Notice to participants at this page about adminship[edit]

Many participants here create a lot of content, have to evaluate whether or not a subject is notable, decide if content complies with BLP policy, and much more. Well, these are just some of the skills considered at Wikipedia:Requests for adminship.

So, please consider taking a look at and watchlisting this page:

You could be very helpful in evaluating potential candidates, and even finding out if you would be a suitable RfA candidate.

Many thanks and best wishes,

Anna Frodesiak (talk) 03:43, 1 September 2016 (UTC)

Cocamidopropyl betaine[edit]

There are two areas were we could use help for Cocamidopropyl betaine, having to due with how we discuss and label it's production. First, the straightforward need to properly source and present how it is produced. We're currently linking to Organic synthesis, which appears to need large amounts of work itself. I'm wondering it might be better not to link to Organic synthesis, but a better quality article on the same topic, as Organic synthesis appears to be more than a bit of a POVFork. I assume there are standard, reliable sources available for how it is produced that editors that frequent this talk page would know.

Second, this chemical is apparently identified as an acceptable ingredient for "natural" products, and there is some dispute over whether or not it should be. This dispute may be nothing more than opposing marketing strategies. No sources have been offered to verify any of this, and the ip that repeatedly brought it up is now focusing on the production aspect instead.

So, we could use help with using proper terminology in the article, linking to proper related articles, and finding sources, especially for how cocamidopropyl betaine is produced. --Ronz (talk) 17:52, 9 September 2016 (UTC)

I have added a better reference for the industrial process of making cocamidopropyl betaine from coconut oil. Whether this chemical is properly classified as "natural" or "synthetic" is not terribly important in my opionon - a lot of baggage is generally implied when people use those terms (especially in light of the common misconception that anything natural is inherently good and anything synthetic is inherently bad). Cocamidopropyl betaine is not found it nature, so in the strictest sense calling it natural would generally be misleading and calling it synthetic would be accurate. Whether it is natural or synthetic is irrelevant to its physical and chemical properties, though, so from a strictly chemical perspective it would be best not to use either term. But to the general reader who might be interested in whether an ingredient in their cosmetics is natural or synthetic, it could very well be an important characteristic. Regarding the article Organic synthesis, currently its focus seems to be more on the laboratory side of organic synthesis rather than the industrial side of organic synthesis (I assume that's what you mean by it appearing to be a POVFork) but it is an appropriate article to link to in my opinion. Chemical process or chemical synthesis might be other options to consider.-- Ed (Edgar181) 00:15, 10 September 2016 (UTC)
Very much appreciated! --Ronz (talk) 15:13, 10 September 2016 (UTC)

Space-filling models of S2 and C2[edit]

Disulfur.png

I'm not sure if this should have been posted some place on Wikimedia Commons, but I don't think there's a place to request files of models of molecules, so I'll out this here instead.

Reviving an archived discussion: the file for disulfur is horribly inconsistent with all the other homonuclear diatomic molecules, which have space-filling models compared to this weird ball-and-stick thing.

On a similar note, no 3D model seems to exist for diatomic carbon. Could one be made? I don't have the neccesary programs.

- AwesoMan3000 (talk) 17:16, 21 September 2016 (UTC)

There is little point for any electronic drawing for diastomic species. What insight/info would such a picture provide?--Smokefoot (talk) 13:13, 22 September 2016 (UTC)
I think the better question is whether this image for disulfur is misleading and whether it could be replaced with anything better. Maybe something like File:Dioxygen-3D-vdW.png but in yellow? EdChem (talk) 06:13, 23 September 2016 (UTC)
Does disulfur even have a double bond? I'm pretty sure that diatomic oxygen is actually a radical with only a single bond, and with sulfur being a heavier analogue of oxygen I'd predict they'd show some form of similarity. - AwesoMan3000 (talk) 11:10, 28 September 2016 (UTC)
I believe so. The ground state for S2 is 3Σg-, the same as for O2 - so you would expect a double bond with a di-radical in the triplet state. However sulfur is group 3 so spin-orbit effects are much larger, making it more reactive in various ways. Thing is, as Smokefoot pointed out, it's pretty much impossible to explain any of this with ball and stick model. You'd need a molecular orbital diagram. --Project Osprey (talk) 13:45, 28 September 2016 (UTC)

{{Hydrides by group}}[edit]

For whatever reasons, an editor has started adding the template {{Hydrides by group}} to all hydrocarbons. That would be a lot of articles. Is this template helpful for readers? My recommendation is that articles be kept austere of tangential information for these reasons: 1) Readers seeking info about 1-octene is extremely unlikely to want to see the periodic table of hydride chemistry (CuH, TiHx etc). 2) Wikipedia is not a textbook. 3) What next? A template for carbon compounds? A separate template for alkenes? One for amines. So for an organometallic cmpd or normally complex natural product, the bottom of the article would have say 10 templates? So the community might think this through. --Smokefoot (talk) 13:13, 22 September 2016 (UTC)

I don't think it makes sense to include a long list of alkanes, alkenes, and alkynes on a template for Binary compounds of hydrogen. Just one link to hydrocarbons would be enough. I agree that putting this template on individual articles for hydrocarbons is completely out of place - inorganic hydrides and hydrocarbons are so different chemically that there is no useful purpose served by including a template for navigating between such disparate topics. I recommend trimming the template and removing it from individual articles about hydrocarbons. -- Ed (Edgar181) 13:25, 22 September 2016 (UTC)
Not planning on adding it to absolutely all hydrocarbons - I can see the obvious problems there. That's why I've only included up to 20 for only three categories of hydrocarbons.
Even at that, it probably shouldn't be removed form absolutely everything. Methane, ethane, propane and butane should probably keep it, but I could definitely see it being removed from pentane and upwards. - AwesoMan3000 (talk) 15:55, 22 September 2016 (UTC)
Offhand, I can't think of many situations in which methane acts as a hydride. Deep space perhaps? Although that might just be some sort of crazy photolysis product. In any even it seems very fringe. --Project Osprey (talk) 17:02, 22 September 2016 (UTC)
Well, the template idea was well intended but the result potentially very confusing.--Smokefoot (talk) 23:02, 22 September 2016 (UTC)
It should stick to the emphasis on groups, and not get carried away with hydrocarbons. Perhaps hydrocarbons could be split to another template just for them. Graeme Bartlett (talk) 05:10, 23 September 2016 (UTC)
I've only listed the first 10 straight alkanes and first 9 of each alkenes and alkynes, and taken it off of any longer ones. - AwesoMan3000 (talk) 08:27, 23 September 2016 (UTC)

I've added labels to the images at Template:Hydrides by group. Currently H2 and HD are listed as hydrogen halides, which they aren't. Should either of these be included at all, given binary hydrides implies hydrogen with some other element? Also, any reason for separating borane and diborane under "boranes" but away from all the other boranes? Thoughts? EdChem (talk) 06:10, 23 September 2016 (UTC)

They don't really seem to follow a general formula like the alkanes, azanes, etc. I could categorise them all under the Boranes section but that might look a bit messy IMO. - AwesoMan3000 (talk) 08:27, 23 September 2016 (UTC)
Placed as they are at present, I think many readers would wonder if they aren't boranes. They are boranes. I think there is potential to confuse / mislead. EdChem (talk) 12:19, 23 September 2016 (UTC)

It's worth noting that hydrocarbons are unlike any other hydrides on this list, in that Carbon is more electronegative than Hydrogen. As such you basically never see hydride abstraction, but you do get addition or substitution reactions instead. Take the simple reaction of a hydride with an acid: methane will react with superacids to give Methanium, which is essentially stable (under the extreme condition at which it is formed). You don't see the abstraction reaction:

CH4 + H+ → CH3+ + H2

As such I don't think they belong on this list, as they don't display hydride chemistry. I understand why they were added, it fills in a black area of a table, which is something that all scientists find very appealing. Unfortunately nature doesn't always conform to well ordered lists and these materials do not belong - or if we are going to include them we should probably explain ourselves somewhere. --Project Osprey (talk) 09:40, 23 September 2016 (UTC)

The text at Hydride#Types of hydrides includes discussion of whether alkanes are hydrides in a technical sense. Note that this "hydrides" template is headed and links to binary compounds of hydrogen, which definitely does include hydrocarbons. Maybe we need to decide which this is. EdChem (talk) 12:25, 23 September 2016 (UTC)
The template was originally created just to link the pages which are currently on the left of the template. And typing "hydrides" is a lot easier than typing "binary compounds of hydrogen".
Maybe we should move it to something like "Binary hydrides"? - AwesoMan3000 (talk) 12:31, 23 September 2016 (UTC)
It seems that there is some research/homework project going on. Otherwise, I dont get it. Categories are being applied that are not needed, are controversial, potentially misleading to nonchemists, etc. There are more useful things to do around here than trying to shoe-horn various compounds into one's notions of categories. --Smokefoot (talk) 13:17, 23 September 2016 (UTC)

3-Methylcyclopropene[edit]

This article is nominated for deletion at Wikipedia:Articles for deletion/3-Methylcyclopropene. Contribution from participants of this WikiProject would be helpful. ChemNerd (talk) 14:39, 23 September 2016 (UTC)