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WikiProject Chemistry (Rated Project-class)
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Discussion of the WikiProject Chemistry - Please add your comment and discussion here. Older discussions are archived.

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This discussion page is about the Chemistry project itself, for detailed, in-depth discussions about specific topics, you'd be best served at the talk page of the specific subject, e.g., Chemicals, Chemical infoboxes, etc. There is also an image request page which might be of interest to you.

European Commission number[edit]

What shall we do with this edit/information? --Leyo 01:22, 5 January 2014

Nobody? --Leyo 21:23, 9 January 2014

Questionable category[edit]

I've found a newly created category that does not have a well-defined candidate definition, and furthermore, its usefulness is not evident. Category:Bulk chemicals. Perhaps, it is a CFD? Plasmic Physics (talk) 09:13, 17 June 2014 (UTC)

"Bulk" is certainly vague, but I don't see a problem with the concept of categorizing chemicals which have high commercial use. Maybe the category could be defined (and/or renamed) along the lines of High production volume chemicals which has an unambiguous definition. -- Ed (Edgar181) 12:48, 17 June 2014 (UTC)
I think commodity chemicals is a less-vague synonym for bulk chemicals. Antony–22 (talkcontribs) 17:49, 17 June 2014 (UTC)
While no disagreement with Antony, to PP I say, forget the IUPAC rigour here: the term has a widely/generally understood meaning. Edgar is correct, but commodity is no less vague, and both are rooted in history of practice. Whether it can be improved or better defined should be the bailiwick of industrial chem experts here, not fly-bys (and not discovery chemists like me, or students or physical chemists). This old chemists opinion. See here for definitions, [1]. Cheers, and hope all is otherwise well, your mate, Le Prof Leprof 7272 (talk) 05:15, 21 June 2014 (UTC)
Apart from its validity in commerce, where safe transport is the issue, it has a further regulatory niche in storage:

"Regulated Chemical Bulk Storage tanks are defined as (6NYCRR Part 596): (i) an aboveground tank storing a hazardous substance, or mixture thereof, with a capacity of one-hundred and eighty-five (185) gallons or greater; (ii) an underground tank storing a hazardous substance or mixture thereof of any capacity; or (iii) a non-stationary tank used to store one thousand (1,000) kilograms (2,200 lbs.) or more of a hazardous substance or mixture thereof for a period of ninety (90) consecutive days or more.​​​​​​​​​​​​​" [See [2]]

You see, after 20-30 years doing something, you can begin to trust instincts. Until then, mate, do the research before acting/suggesting. (You could have found this as well as I.) Le Prof Leprof 7272 (talk) 05:34, 21 June 2014 (UTC)
Honestly, what are you talking about? I came here for a second opinion, as is appropriate. Plasmic Physics (talk) 06:06, 21 June 2014 (UTC)
Answered at the appropriate User Talk page. Le Prof Leprof 7272 (talk) 00:14, 22 July 2014 (UTC)

Wiki Interactive Periodic Table needs to be consistent with standard periodic table.[edit]

The content of https://en.wikipedia.org/wiki/Periodic_table is okay.

What does need changing is the format of the interactive periodic table that Wiki shows for each element. For all the elements this non-standard and unusual periodic table shows at the top right corner. For example Carbon: http://en.wikipedia.org/wiki/Carbon

Why have Wiki programmers not used a periodic table format that looks like either of the first two periodic tables listed at https://en.wikipedia.org/wiki/Periodic_table ? This format is self-consistent with IUPAC, NIST, etc.

IUPAC Periodic Table. http://www.iupac.org/fileadmin/user_upload/news/IUPAC_Periodic_Table-1May13.pdf National Institute of Standards and Technology, Periodic Table. http://www.nist.gov/pml/data/images/PT-2013-Large_2.jpg

Using a non-standard periodic table is misleading and the interactive periodic table shown on Wiki for each element is incorrect.

Historical discussion of alternative, proposed, and (now considered) incorrect periodic tables is fine. But using a non-standard periodic table format for all the individual elements is not.

Wiki needs to display the commonly accepted format for the interactive periodic table shown for each element: http://en.wikipedia.org/wiki/Periodic_table#mediaviewer/File:Periodic_table_(polyatomic).svg It is the same as shown in the first two images at https://en.wikipedia.org/wiki/Periodic_table. — Preceding unsigned comment added by 128.97.138.12 (talk) 23:11, 18 June 2014 (UTC)

It's not incorrect: it just puts the lanthanides and actinides in the main body of the periodic table, which is where they should go according to the asterisks in the main periodic table. I guess it could be a bit confusing without the element symbols, but it is equivalent to the 18-column periodic table.
The 18-column format is widely used mostly due to space limitations on paper, but I wouldn't mind changing it to that for the purpose of recognizability (the cells would have to be slightly bigger to preserve the width, but it would become easier to click on a particular element). With the symbols included, like in the periodic table footer on each element, I think there is no problem with using a 32-column periodic table.
Nevertheless the 18-column periodic table might be a bit confusing without the symbols: you don't know then if the convention being used is to put lanthanum or lutetium below yttrium, or none of them. With the 32-column table, you can tell between these alternatives by checking if the d-block is broken. Double sharp (talk) 02:38, 19 June 2014 (UTC)

You just single-handedly decided to ignore IUPAC, NIST, and over 100 years of periodic table history.

The placement of lanthanum (and later on actinium) under scandium and yttrium in group 3 (IIIB) has been the standard for many years; for example, the first edition of the CRC Handbook of Chemistry and Physics published 1913, page 70 titled, “Periodic Arrangement of the Elements – Mendelejeffs (Revised to 1911)” (1), and the Handbook of Chemistry published 1946 (2). This placement continues to be the standard; for example, the CRC Handbook of Chemistry and Physics (which I have access to many editions published 1968-2008) (3), the IUPAC (4), and the NIST (5).

1. CRC Handbook of Chemistry and Physics, 1st Ed., Editor David R. Lide, CRC Press, 1913, pg. 70. 2. Handbook of Chemistry, 6th Ed., Editor Norbert A. Lange, Handbook Publishers, 1946, pg. 58. 3. CRC Handbook of Chemistry and Physics, 89th Ed., Editor David R. Lide Jr., CRC Press, 2008. 4. IUPAC Periodic Table. http://www.iupac.org/fileadmin/user_upload/news/IUPAC_Periodic_Table-1May13.pdf 5. National Institute of Standards and Technology, Periodic Table. http://www.nist.gov/pml/data/images/PT-2013-Large_2.jpg

Please click on the IUPAC and NIST links. The Wiki interactive periodic table is clearly incorrect. You will not see the Wiki interactive periodic table in chemistry textbooks.

There are many problems with the Wiki interactive periodic table:

The biggest error is La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 are placed in the f-block even though they have no outer electrons in the f-state. As you can see from the Wiki article content La and Ac are in the first position in the d-block (Group 3) with their d1 state as they have outer electrons in common with the d-block.

Insertion of the f-block (even if done correctly which the Wiki interactive periodic table does not) is not advised for multiple reasons:

Insertion of the f-block results in these 14 elements having no group numbers (in order to maintain the original group 1-18 designations). Or one has to renumber all the groups 1-32. Halogens would then be group 31. This will never be adopted as the group numbers help explain the element properties in that group. Group 31 for the halogens (F, Cl, etc.) gives no meaning. Or keep the original group 1-18 designations and assign some other group assignment to the f-block elements. In addition to being inconsistent with most of the periodic table this would add another difficulty. Elements within a group have similar properties or trends and adjacent groups different properties. Applying this to the newly labeled groups in the f-block is not appropriate/possible.

Did it not occur to you that the Wiki interactive periodic table is causing much confusion for chemistry students who see 14 elements with no group numbers, the elements La and Ac with their outer d1 state in the f-block, etc. There is very good reason why the f-block is not "just" inserted to make the periodic table look nice.

Please change the format of the Wiki interactive periodic table to look the same as International Union of Pure and Applied Chemistry, National Institute of Standards and Technology, etc. It is the same standard periodic table as commonly accepted and shown at the beginning of https://en.wikipedia.org/wiki/Periodic_table .

First of all, I did not single-handedly decide this, and I am not ignoring history.
The placement of lanthanum and actinium under yttrium may have been standard for many years, but this is also changing and IUPAC chooses not to recommend a specific form (their table places neither La nor Lu under Y). There are many good arguments on both sides. And yes, Sc-Y-Lu-Lr periodic table have appeared in textbooks: one example is Wulfsberg's Inorganic Chemistry. As can be seen from "The Flyleaf Periodic Table", this usage does not appear until after 1982, when Jensen's paper "The Positions of Lanthanum (Actinium) and Lutetium (Lawrencium) in the Periodic Table" first appeared. Thereafter textbooks are about evenly split between your proposed form (14CeTh) and the current form used at the top of the infobox (14LaAc), with a few attempting to stay neutral and use IUPAC's 15LaAc.
As Jensen says in his 2008 or 2009 paper (I think it's the former), the criteria for placing an element in the periodic table is to assign it to a block based on the orbitals its valence electrons are in, assigning it to a group based on the number of valence electrons it has available, verifying the validity of these assignments through checking trends across the block, group, and period in question, and finally verifying that the arrangement results in the elements appearing in order of increasing atomic number. For whether to place La or Lu below Y, we must go to the third criterion, as the first two don't provide a definitive answer. And indeed Jensen makes a strong case for Lu below Y in his 1982 paper, based on the properties of the elements in question and the trends that result from each choice.
Why is the anomalous electron configuration of La and Ac absolutely prohibitive when it comes to assigning them to the f-block? By that argument thorium is also a d-block element, given its electron configuration of [Rn]6d27s2! But nobody calls it that. Lawrencium has been experimentally measured to have an electron configuration of [Rn]6f147s27p1: but does anyone call it a p-block element? And if it can be considered an f-block element with an anomalous electron configuration, why can it not be considered a d-block element with an anomalous electron configuration? I think a better way of looking at the electron configuration of La and Ac is that, like Gd and Cm, they have anomalous electron configurations to get the stability of an empty (or in the latter case half-filled) f orbital, and are really f-block elements. Finally, in lutetium, the 4f electrons are not valence electrons: therefore it does not make sense to assign it to the f-block.
Group numbers have never been officially assigned to the f-block elements (some have tried), but is this not exactly the same situation as if they are detached from the main table? They still have no group numbers either way, and each column in the f-block still has only two elements at present. I agree with you that assigning group numbers to these columns is nonsensical due to the lack of any trends that should be present in a group, but surely inserting the f-block back into the main body doesn't change this situation.
While group 31 for the halogens gives no meaning, neither does the IUPAC-approved group 17. The halogens all have seven valence electrons and the group number that would be best for them is surely group 7 (VIIA, VIIB, VII – whichever style you prefer): this number is far more useful than 17, for example in the (8−n) rule.
The bottom line is that IUPAC allows both forms of the periodic table, either Sc/Y/La/Ac or Sc/Y/Lu/Lr. The long form periodic table is simply a differently laid-out version of the medium form periodic table that you will normally see, and is not as often seen merely because of the aspect ratio of paper fitting the medium form well and not the long form. This is not a constraint here, and prominent authorities such as Seaborg have preferred the long-form periodic table. Double sharp (talk) 12:29, 19 June 2014 (UTC)

IUPAC and NIST most definitely do place La and Ac under scandium and yttrium in group 3. The IUPAC table you reference clearly numbers elements 57-71 with La(57) under Y and again clearly numbers elements 89-103 with Ac(89) under La.

The vast majority of references, including IUPAC, NIST, and the Wiki page https://en.wikipedia.org/wiki/Periodic_table place La and Ac under scandium and yttrium in group 3. To state otherwise is simply not true.

The placement of lanthanum (and later on actinium) under scandium and yttrium in group 3 (IIIB) has been the standard for many years; for example, the first edition of the CRC Handbook of Chemistry and Physics published 1913, page 70 titled, “Periodic Arrangement of the Elements – Mendelejeffs (Revised to 1911)”, and the Handbook of Chemistry published 1946. This placement continues to be the standard; for example, the CRC Handbook of Chemistry and Physics, the IUPAC, and the NIST.

There is certainly room for discussion of alternative representations of the periodic table but to show the current Interactive Wiki Periodic Table and defend it as the commonly accepted form is without basis.

What is troubling is your defense of this non-standard format and then defending it on the basis that it is better than the standard format. In addition your justification comes across as informed but a good deal of it is obfuscation. Most unusual for a neutral wiki volunteer.

If IUAPC, NIST, etc., intended to place Lu and Lr in group 3 in the d-block they would have done so. The current incorrect Interactive Wiki Periodic Table places Lu and Lr in group 3 in the d-block.

You state IUPAC, NIST, etc., do not insert the f-block due to a lack of space on the printed page yet you give an online IUPAC reference. There is no restriction to IUPAC and NIST showing the inserted f-block online yet they do not (for the good reasons stated above; and it results in a gap between the group 3 elements (Sc, Y, La, Ac) and the group 4 elements. The preference, historically, has been to show gaps between blocks as a visual aid not within blocks).

This discussion is not a printed page format issue.

La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 are in the first position in the d-block (Group 3) because of their d1 electronic ground state and properties. The Wiki Interactive table does not show this.

Instead the Wiki Interactive periodic table shows La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 in an unnamed group in the f-block yet both elements have no outer electrons in the f-state (as clearly shown by their electron configurations).

Why is a wiki volunteer defending a non-standard periodic table with invalid statements?

Using your reasoning Cu, [Ar]3d10 4s1 and Zn, [Ar]3d10 4s2 would be moved to the s-block.

Lu, [Xe]4f14 5d1 6s2 and Lr, [Rn]5f14 7s2 7p1 are best left in the f-block because both elements have outer electrons in the f-state (as clearly shown by their electron configurations).

The Wiki Interactive Periodic Table format must be self-consistent with the format of other online periodic tables by established scientific bodies such as IUPAC and NIST. — Preceding unsigned comment added by 100.32.69.62 (talk) 02:52, 20 June 2014 (UTC)

No, they don't. If they had wanted to unequivocally dictate that the composition of group 3 is Sc/Y/La/Ac, they would have done so by putting La and Ac in the main body, followed by a note leading to the lanthanides and actinides at the bottom of the periodic table. So group 3 would look like Sc/Y/La/Ac: followed by a space with boxes reading (58-71) and (90-103): and then group 4 (Ti/Zr/Hf/Rf). This is not what IUPAC does: they sidestep the issue. How do you know they didn't literally mean that all the lanthanides and actinides fitted under Sc and Y?
The online IUPAC reference is the one you yourself mentioned, and that is why I commented on it. The medium period layout probably stemmed from page limitations IIRC. While it is still commonly used even elsewhere (I would imagine because the Web gives you freedom to use any aspect ratio you'd like, and it's easier to use the traditional format), now that the restriction is not present, it is absolutely OK to use an equivalent form. In fact we don't always use the long form: we just use it here because the medium form won't fit the limited width as well. This isn't even something like using the Janet periodic table (putting He over Be) or some of those formats that put Be and Mg over Zn, etc. All the elements are in the same locations as the medium table implies they are. As for the La/Lu issue, different forms of the medium table imply differently on this issue.
No, La and Ac are not d-block elements, as I have said earlier: they are f-block elements with anomalous electronic configurations. Or do you think the electron configurations of almost all the f-block elements are anomalous, because most of them don't have the 5d1/6d1 electron that was filled in La and Ac? Even their properties indicate this: the trends you get when plotting Sc-Y-Lu resemble the d-block groups very closely, unlike the trends you get when plotting Sc-Y-La. See Jensen's 1982 article for some graphs. Putting La and Ac in the d-block means that in group 3 alone (and in none of the other d-block groups), there is no addition of the filled 4f14 subshell when going down from period 5 to period 6.
Please read carefully. I never said that thorium was a d-block element: I merely pointed out that by your argument it should be one because of its [Rn]6d27s2 electron configuration. Naturally I disagree with that, and hence I think that Cu and Zn should be handled the same way: they are d-block elements, although Cu has an anomalous [Ar]3d104s1 electron configuration.
Finally, if you're using the standard definition of what an outer electron is (I'm assuming a valence electron), the f electrons in Lu and Lr are not outer electrons as they don't participate in chemical bonding: the 5d1 and 6s2 electrons of Lu are lost to form the Lu3+ ion, with the 4f electrons firmly part of the core and not participating in chemical reactions (the 4f shell being well-localized near the atomic nucleus). Just like the next elements (Hf and Rf) the s and d electrons (p instead for Lr) are the valence electrons, and hence these elements are in the d-block. Double sharp (talk) 05:01, 21 June 2014 (UTC)
(P.S. I wouldn't oppose changing the long table to a medium table if there was a clear consensus to do so, but the issue has been raised several times and there never seemed to be one each time. What I personally cannot support is following Sc/Y/La/Ac when arguments based on the properties of the elements oppose this format and IUPAC and NIST do not use it. Sc/Y/*/** would be the best, remaining neutral, but that is tricky to do with the long table without grotesquely stretching the Sc and Y cells: hence for the long table Sc/Y/Lu/Lr is probably best.) Double sharp (talk) 05:09, 21 June 2014 (UTC)
re IP. An introduction. Here I'll write about the graphical presentation, which is secondary to the facts we actually want to show. A PT graph follows scientific statements. I have shaped many of the PT's here at enwiki, usually following an outcome of a discussion at WT:ELEMENTS. This is about the drawing of PTs; the actual facts the PT shows is beyond my area of knowledge (I can read & follow those PT content discussions, but not make new statements). I note that similar discussions exist for: which are the metalloids?, are group 12 elements a post-transisiton metals?, what to name those post-transition metals after all?, and —less hot— the placement of hydrogen (H). At this point, please note that all these are not internal wiki issues, but they reflect topics as they exist in the scientific world.
In most or all PTs at en:wikipedia, when we show a positioning it is that group 3 is Sc/Y/Lu/Lr. This is usually a 32-column PT. In 18-column PTs, we show group 3 and the asterisks being ambiguous (as in this PT).
Let me split the topic. IP conflates the PT graph with statements of element positioning. The group 3/f-block/La&Ac/Lu&Lr/ topic as scientific statements and facts is independent of and prior to any presentation form. The PT graphic should simply represent whatever the outcome is, maybe even showing an ambiguity in the theories. From this I note that IP says (my words): "the 18-column form is better because it shows the facts as they are correct". Whether these statements are correct and which statements to use in our PTs, I'll leave to others for now (Double sharp addresses this above). Such a scintific debate can very well be described in an article or article section, for example in group 3.
18-column variants. Contrary to what IP seems to think, there is no single 18-column PT standard with regard to this issue. We could also show an 18-column PT with Lu/Lr in group 3 explicitly; a statement IP opposes. So "the" 18-column format does not say anything about these placements.
Graphic clarity. For any graphic presentation, I require that it is unambiguous in what it conveys. (If we want to show the dual options for hydrogen, then we must find a way to show that scientific ambiguity graphically unambiguous!). We should not ever put graphic ambiguity on the readers screen. In this topic of the outplaced set of elements, it must be clear how to position that satellite elements back into the periodic table. This cut-and-paste exercise may not introduce any unclarities or questions, either when taking them out to below or putting them back in. I repeat: no graphic ambiguity.
The solution IP proposes make use of the graphic ambiguity of the 18-column PT: that 18-column variant graphically hides the group 3 discussion, it simply does not show any facts or discussion. But in a 32-column presentation we cannot hide it. Again, I refuse to use an 18-column PT because of this 'advantage'. It leaves the reader with questions.
18-column PTs questioned. Actually, our commonly used PT (such as the first one here) does have an ambiguity. The asterisks show the replacement positions of the two elements rows clearly (I hope). But when I cut-and-paste 15 elements in there (say the LN), I have no clue as to what happens with that group 3 column. Are those 15 elements squeezed into one cell (a sin in PT structuring, but graphically suggested)? Are Sc/Y glued to group 2 or to group 4? Are Sc and Y cells somehow stretched to span the whole area between group 2 and group 4? This is the graphical imperfection in the PT we use. (btw, all of this could be clarified by adding a gap column between groups 2–3 [3] or between groups 3–4. This requires a choice of group 3 completion as is our topic here).
The IUPAC PT that IP has linked to [4] is a graphically a rejectable form and a horror. Those vertical dashed lines making a vertical connection in group 3: what does that say? Are La and Ac really below there in group 3 (suggesting some extra periods)? Or if I copy-paste elements La and Ac into periods 6 and 7, what to do with the remaining 2×14 elements? Are these Desert Island elements? And still the gap question for periods 4 and 5 is not clarified. IUPAC should never have shown this graph to the world.
Some more bad graphics (what does the graph say about the group 3 area? How to cut&paste LN/AN?): [5], [6], [7] (ouch), [8], [9], [10],
Also, I find it a bit weird to use "historical" as an argument. The PT structure has always been adjusted in its 150+ years. Why use a form 100 years old when the LN/AN were not even recognised?
Conclusion. The topic IP raises should be split into 1. what facts to show (periodic table scientific), and 2. then follows: how to show that outcome unambiguously in any PT. I am amxious to learn what facts we should show. If someone can show it in a 32-column PT, we can graph that into an 18-column for sure. -DePiep (talk) 12:28, 22 June 2014 (UTC)
Yes indeed, the historical argument is quite weak: if we're going to use this argument, why not go back to the beginning of the story and use Mendeleev's original 8-column short-form periodic table? It's still very popular in the CIS even now. Double sharp (talk) 13:21, 22 June 2014 (UTC)
re IP: The Wiki Interactive Periodic Table format must be self-consistent with the format of other online periodic tables by established scientific bodies such as IUPAC and NIST
NIST? Never heard of, never met a link! That's the "National institute of Standards and Technology" then (which Nation??). But thanks. Now, for the moment, about their "standards". The NIST PT graph (nice!) still does not resolve the group 3 area: when I insert the LN/AN elements in there as they show, what or where or how are Sc/Y to go?
Your IUPAC PT, as I wrote above, has an illegible graph. I wrote: It is a graphically a rejectable form and a horror. Those vertical dashed lines making a vertical connection in group 3: what does that say? Are La and Ac really below there in group 3 (suggesting some extra periods)? Or if I copy-paste elements La and Ac into periods 6 and 7, what to do with the remaining 2×14 elements? Are these Desert Island elements? And still the gap question for periods 4 and 5 is not clarified. IUPAC should never have shown this graph to the world.
Please, please show me your 32-column PT. -DePiep (talk) 01:40, 24 June 2014 (UTC)
I think what (s)he wants is a 32-column table where La and Ac are in group 3, and the remaining 2×14 elements are spliced between La and Hf, like this one. (That old revision moreover gives the first 4 hypothetical period 8 elements, to show where they would fit. But it breaks all the blocks except the p-block.) Double sharp (talk) 15:14, 24 June 2014 (UTC)

Yes IUPAC side-steps the issue of the ‘best’ periodic table format/presentation for many good reasons. Some of which have been discussed above (f-block elements have no group numbers; “Elements within a group have similar properties or trends and adjacent groups different properties. Applying this to the newly labeled groups in the f-block is not appropriate/possible.”; visual gap within a block; etc.)

However the IUPAC has publications which make clear the group 3 elements are Sc, Y, La, Ac. For example the 2014 publication:

IUPAC-NIST Solubility Data Series. 100. Rare Earth Metal Fluorides in Water and Aqueous Systems. Part 1. Scandium Group (Sc, Y, La)

They do this because of over 100 years of placing La in group 3. See detailed comments and references above.

The group 3 d-block elements are: Sc, [Ar]3d1 4s2 Y, [Kr]4d1 5s2 La, [Xe]5d1 6s2 Ac, [Rn]6d1 7s2

The Wiki Interactive Periodic Table places La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 in the f-block. This creates many problems and is a step backwards.

If we start moving elements around because of ‘anomalous’ electronic configurations then there are many elements that need moving. One cannot selectively justify one argument for moving some elements and not apply the same to other elements.

If one applies your reasoning that Lu and Lr do not belong in the f-block because, “the 4f electrons firmly part of the core and not participating in chemical reactions”, then that means the entire 4f elements/row don’t belong in the f-block!

Lu, [Xe]4f14 5d1 6s2 and Lr, [Rn]5f14 7s2 7p1 are best left in the f-block because both elements have outer electrons in the f-state (as clearly shown by their electron configurations). This is commonly accepted practice, e.g., http://www.rsc.org/periodic-table/element/71/lutetium

Keeping Lu, [Xe]4f14 5d1 6s2 and Lr, [Rn]5f14 7s2 7p1 in the f-block makes sense for several reasons. Even though the tightly held 4f electrons in the lanthanides do not participate in chemical reactions the 4f electrons do play a role in their properties. It is for this reason there is active research in lanthanide-doped semiconductors with small amounts of lanthanide ions and the important role of their 4f transitions. For example the publication titled, “Synthesis, Structure, and Molecular Orbital Studies of Yttrium, Erbium, and Lutetium Complexes Bearing Pyrazolato Ligands: Development of a New Class of Precursors for Doping Semiconductors”.

The Wiki Interactive Periodic Table incorrectly removes Lu, [Xe]4f14 5d1 6s2 from the f-block and incorrectly places La, [Xe]5d1 6s2 in the f-block, yet there is obviously no way the 4f electrons in La can play any role in any process because it has no 4f electrons!

For all the detailed defense of the unusual Wiki Interactive Periodic Table it is surprising that there is any confusion as to what standard format I am referring to. As already stated many times the format of the first two periodic tables listed at https://en.wikipedia.org/wiki/Periodic_table are fine to use for the Wiki Interactive Periodic Table, as are the IUPAC periodic table http://www.iupac.org/fileadmin/user_upload/news/IUPAC_Periodic_Table-1May13.pdf, the National Institute of Standards and Technology periodic table http://www.nist.gov/pml/data/images/PT-2013-Large_2.jpg, or any of these:

Although I would recommend the Wiki Interactive Periodic Table uses the IUPAC format.

Please note I am not asking or suggesting that the discussion of these problems not be present in Wiki articles of which there are 100’s of Wiki pages on the periodic table and the individual elements.

However the current Wiki Interactive Periodic Table is definitely a misrepresentation of what is the commonly accepted format (see IUPAC, NIST, https://en.wikipedia.org/wiki/Periodic_table).

The current Wiki Interactive Periodic Table incorrectly places La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 in the f-block and incorrectly places Lu, [Xe]4f14 5d1 6s2 and Lr, [Rn]5f14 7s2 7p1 in the d-block. The word “incorrectly” is used for the many reasons discussed here and above. — Preceding unsigned comment added by 128.97.138.12 (talk) 23:26, 24 June 2014 (UTC)

No, it doesn't mean that the entire row doesn't belong in the f-block. To take the example of Yb (although it will really work for any lanthanide except La and Gd), [Xe]4f146s2, two 6s and one 4f electron are ionized to make the tripositive ytterbium cation with electron configuration [Xe]4f13. Clearly the 4f electron is active here. Indeed this holds for every lanthanide except La and Gd, which have anomalous electron configurations, as I have said many times. (Ce's 4f electron is ionized when it is oxidized to Ce4+.) And this says nothing about other elements: many also have anomalous electron configurations, like Cr, Cu, Pd, etc. Is it so hard to believe that La and Ac are also like this? And why do your arguments suggest that Lr's [Rn]5f147s27p1 electron configuration prohibits it from being a d-block element, but has absolutely no bearing on whether it is an f-block element?
You don't have to move any other elements. Cu is in group 11, as that is where it would be if it had the expected [Ar]3d94s2 electron configuration. Thus La is the first f-block element, as that is where it would be if it had the expected [Xe]4f16s1 electron configuration. Lu presents no argument with its [Xe]4f145d16s2: it has the right configuration to be under Y. After all Hf with [Xe]4f145d26s2 is under Zr.
I can handle a visual gap in the d-block, and you don't even need one in Sc/Y/La/Ac if the cells read Sc/Y/La*/Ac** or similar. And simply removing the f-block from the main table doesn't solve the problem of the f-block columns: they are still columns, and the outermost ones are still adjacent to groups 2, 3 or 4 (depending on format), because that is where the asterisks seem to be telling me to place them. Double sharp (talk) 02:44, 25 June 2014 (UTC)

On the basis that Lu 4f electrons do not participate in bonding you stated it as a reason not to include Lu in the f-block. The 4f electrons for all the Lanthanides do not participate in bonding, and we are in agreement this is not a reason to remove them from the f-block. This shows the importance of electron configurations and where elements are placed, and Lu [Xe]4f14 5d1 6s2 which is nearly always Lu3+ [Xe]4f14 has outer 4f electrons that can play a role as discussed above in the example of lanthanide-doped semiconductors.

That is why their publication is titled, “Synthesis, Structure, and Molecular Orbital Studies of Yttrium, Erbium, and Lutetium Complexes Bearing Pyrazolato Ligands: Development of a New Class of Precursors for Doping Semiconductors”.

It is not titled, “Synthesis, Structure, and Molecular Orbital Studies of Yttrium, Erbium, and Lanthanum Complexes Bearing Pyrazolato Ligands: Development of a New Class of Precursors for Doping Semiconductors”, for the obvious reason that La, [Xe]5d1 6s2 has no 4f electrons.

I am also in full agreement with your statement, “I can handle a visual gap in the d-block, and you don't even need one in Sc/Y/La/Ac if the cells read Sc/Y/La*/Ac** or similar.” This what the IUPAC, NIST and the above examples do. When will the Wiki Interactive Periodic Table show this format? — Preceding unsigned comment added by 128.97.138.12 (talk) 19:32, 26 June 2014 (UTC)

As I have said many times above, no, they don't. They use Sc/Y/*/**. Double sharp (talk) 14:13, 1 July 2014 (UTC)
IUPAC doesn't have a position on the composition of group 3. A number of chemists in the 1920's and 30's assigned Lu rather than La to group 3 on the basis that the chemical properties of Y, and Sc to a lesser extent, were closer to Lu. That La and Ac are sometimes shown as group 3 members appears to have originated in the 1940s based on electronic configurations and the concept of the differentiating electron. As noted, arguments as to the composition of group 3 should turn upon more than the single concept of a differentiating electron. There remains a reasonable body of physics and chemistry-based evidence favouring the assignment of Lu and Lr to group 3. Eric Scerri has recently presented arguments [11], including those based on the construction of the 32-column form of the periodic table, supporting the assignment of Lu and Lr to group 3. IUPAC have since asked him to form a working group with a view to making this change official. See also Jensen's 2009 commentary on this question, here. Sandbh (talk) 11:36, 25 June 2014 (UTC)

IUPAC has for many years not wanted to force this issue because there is no one correct periodic table format when it comes to the f-block. But what is clear is the preferred representation as shown by: the first two periodic tables listed at https://en.wikipedia.org/wiki/Periodic_table the IUPAC periodic table http://www.iupac.org/fileadmin/user_upload/news/IUPAC_Periodic_Table-1May13.pdf the National Institute of Standards and Technology periodic table http://www.nist.gov/pml/data/images/PT-2013-Large_2.jpg

And 2014 publications such as “IUPAC-NIST Solubility Data Series. 100. Rare Earth Metal Fluorides in Water and Aqueous Systems. Part 1. Scandium Group (Sc, Y, La)” are unambiguous.

I agree with you that the 18-column form is prevalent. I don't like the fact that the lanthanides and actinides are relegated to the status of footnotes, nor do I like the fact that the IUPAC table shows 15 lanthanides, rather than 14, due to indecisiveness as to the composition of group 3. Since the 18 column-form is prevalent it's reasonable to show this as the Wikipedia periodic table. Given the shortcomings of this form I think having the 32-column form in element infoboxes is a reasonable way of accommodating (a) prevalence and (b) showing what's really going on. Sandbh (talk) 00:11, 29 June 2014 (UTC)

“That La and Ac are sometimes shown as group 3 members appears to have originated in the 1940s based on electronic configurations and the concept of the differentiating electron.” Sorry but this 100% incorrect.

Lanthanum was placed under scandium and yttrium in group 3 over 100 years ago. See the first edition of the CRC Handbook of Chemistry and Physics published 1913, page 70 titled, “Periodic Arrangement of the Elements – Mendelejeffs (Revised to 1911)”.

Lanthanum was placed under scandium and yttrium in group 3 in the major chemistry reference books and still is. Examples are the Handbook of Chemistry published 1946 and decades of the CRC Handbook of Chemistry and Physics.

I should've been clearer. IMO, since about the 1940s, authors who show La in group 3 have done so explicitly on the basis of the electron configuration argument; or tacitly on the basis of how other authors have depicted their PTs. In both cases, strong physical and chemical arguments for placing Lu in group 3 have been discounted or overlooked. Sandbh (talk) 00:11, 29 June 2014 (UTC)

The Scerri link refers to Jensen’s early paper and Jensen’s paper is selective in omitting the reasons why La and Ac were and are placed in group 3.

He discusses the relevance of electron configurations well enough, I think. And he gives the physical and chemical arguments for his case. Sandbh (talk) 00:11, 29 June 2014 (UTC)

You are restating what I wrote, he did provide the physical and chemical arguments for his case. He did not discuss the physical and chemical arguments for why La and Ac were and are placed in group 3 and the implications of moving La and Ac to the f-block (which are discussed above).

One has to look at the pros, cons, and implications of placing elements in the periodic table or changing their positions.

In addition the f-block, as discussed in above previous posts, are not groups like the other periodic table groups and this is a reason not to insert them or one ends up with unnumbered/unnamed/non-groups being presented as groups. Hence the IUPAC presentation which they are unlikely to change.

See here, for an alternative view, including that of Eric Scerri. Sandbh (talk) 00:11, 29 June 2014 (UTC)

However whatever changes are proposed the Wiki Interactive Periodic Table should be reflecting what is the preferred periodic table presentation as shown by: the first two periodic tables listed at https://en.wikipedia.org/wiki/Periodic_table the IUPAC periodic table http://www.iupac.org/fileadmin/user_upload/news/IUPAC_Periodic_Table-1May13.pdf the National Institute of Standards and Technology periodic table http://www.nist.gov/pml/data/images/PT-2013-Large_2.jpg etc. (see links in previous post).

(As an aside where was Jensen’s emotional commentary published? Jensen has formatted it to look like a journal publication but I could not find it.) — Preceding unsigned comment added by 128.97.138.12 (talk) 20:27, 26 June 2014 (UTC)

I understand it was published in a condensed form in the Journal of Chemical Education. I further understand that his commentary may appear to be somewhat emotional as he perceived that he had been subjected to an "ad hominen" attack, without warning. PS: I collapsed your earlier links as they display poorly on my ipad. Sandbh (talk) 00:11, 29 June 2014 (UTC)

Most unusual to show a paper in journal format, and have it referenced by others as a publication, when it is not a journal publication.

Here is the condensed form Sandbh refers to. Double sharp (talk) 15:14, 8 July 2014 (UTC)

List of 2,4-D manufacturers[edit]

Are lists like the one mentioned above of any use or significance? --Yikrazuul (talk) 09:08, 29 June 2014 (UTC)

No. Only thing I can brainstorm would be if some special notability of their doing so (together forming a coalition or trade-group, or being together involved in some major legal or other newsworthy situation, etc.). Even then, seems likely to be unworthy of a stand-alone list article. Unless there's something notable about this group as a whole or the members of it doing the identified activity, I think at best it's just a business directory; see also Wikipedia:STANDALONE. Given the chemical involved (which might be controversial in various ways), we need to be especially careful not to make any negative connotations or implications by placing such a prominent identifier on the listed companies. DMacks (talk) 04:12, 1 July 2014 (UTC)
I have AfD'd the article. As I state there, the opening statement could be used in the article about the compound, the list is not necessary. I find this article/principle also US-centered, this is not a 'List of 2,4-D manufacturers', this is a 'List of 2,4-D manufacturers in the US'. --Dirk Beetstra T C 10:22, 1 July 2014 (UTC)

Isomer names[edit]

The article Citral clearly states that citral is either or both two different substances, geranial and neral, which are cis-trans isomers. Yet in its infobox, the article gives a single IUPAC name, CAS number, PubChem number, ChemSpider number etc. for "citral". I had assumed that these names and numbers were meant to be identifiers. Was this naive of me? or is the infobox misleading? Maproom (talk) 12:42, 29 June 2014 (UTC)

Citral is a mixture, so unless the isomers rapidly interconvert at standard conditions, is does not even warrant a Chembox. A table with a few simple properties at common compositions, and content describing how the properties vary with composition, should suffice. That being said, mixtures can also have identifiers, to an extent. The rule of thumb is, if you are in doubt over whether an E/Z mixture is separable, it usually is. Plasmic Physics (talk) 21:44, 29 June 2014 (UTC)

Both the mixture and pure isomers appear to have separate identifiers, that along with the common names would imply relative stability. Given time and effort the chembox could be expanded to include all the variables. However, I should point out that chembox code isn't really designed for this, I did it once for periodic acid and that involved using some of the parameters in ways they weren't intended to be.

E/Z-citral E-citral Z-citral
Cas 5392-40-5 141-27-5 106-26-3
Chemspider 9372550 553578 558878
Pubchem 8843 638011 643779

On a side note, it appears that the name 'geranial' has something to do with with the Geraniums. Likewise Neral appears to be derived from Neroli. Project Osprey (talk) 23:00, 29 June 2014 (UTC)

Geraniol has also been called “lemonol” and “rhodinol” (rose). Its structural isomers include linalool (lignum-aloes), citronellal or rhodinal, eucalyptol, lavandulol, and menthone (mint).—Odysseus1479 01:03, 30 June 2014 (UTC)

The chembox should here just be having the data for the mixture, and in the text it should link to the E and the Z compounds' articles. This chembox on Citral may become a bit minimalistic. Don't think too binary about it. --Dirk Beetstra T C 03:53, 30 June 2014 (UTC)

Some other articles dealing with pairs of enantiomers are carvone and malic acid: each has a single chembox, giving a single IUPAC name. Would such articles be better with two chemboxes, one for each substance? (I don't think infoboxes are restricted to one per article: Klein graphs has two infoboxes, one for each graph.) Is there a reliable free online source where I can look up official names for organic chemicals? Maproom (talk) 10:25, 30 June 2014 (UTC)
No, an article can only have one Chembox, that much is stated explicitly somewhere. And again no, there is no reliable source for official names. Plasmic Physics (talk) 10:52, 30 June 2014 (UTC)
Agree with Beetstra: One doesnt need to get too litigious about chemboxes and isomers. Lots of compounds are available as mixtures and readers want some data on that mixture. We serve readers, period. We adapt to the chemistry, chemistry does not adapt to Wikipedia. It takes expertise to interpret data, but that is always the case. --Smokefoot (talk) 12:32, 1 July 2014 (UTC)

Talk:Coatings[edit]

FYI, significant number of mislinks heading to wrong article. Discussion needed on what to do with redirect. In ictu oculi (talk) 10:49, 30 June 2014 (UTC)

AfC Submission - Anion Exchange Resin[edit]

Got a chem-related submission at Draft:Anion Exchange Resin. Looks good at first glance to me, but I'm curious about the overlap with ion-exchange resin (if any). Is anion-exchange resin particularly notable enough to have its own article, or should it possibly be merged with ion-exchange resin? Looks like a lot of overlap coverage between the two pages, and unfortunately chemistry wasn't my forte in high school. Thanks, ~SuperHamster Talk Contribs 23:28, 30 June 2014 (UTC)

An anion exchange resin is a type of ion exchange resin. Cation exchange resins also exist, as explained in the ion exchange resin article. In my view the draft anion exchange resin article should be rejected, as its material is already covered, better, in the ion exchange resin article. Maproom (talk) 05:59, 1 July 2014 (UTC)
I also note that the list of "common anions" in Draft:Anion Exchange Resin, as well as having numerous errors, starts with hydride ions. You won't get hydride ions in an ion exchange resin - they react vigorously with water. Maproom (talk) 13:27, 1 July 2014 (UTC)

Noyori asymmetric hydrogenation[edit]

Can some people have a look at Talk:Noyori asymmetric hydrogenation?. Thanks! V8rik (talk) 21:32, 7 July 2014 (UTC)

Probably should start by defining the term "Noyori asymmetric hydrogenation" because it is difficult to discuss mechanisms without knowing the process being analyzed. Not trying to be snarky here, but Noyori and co invented a lot of catalysts that hydrogenate ketones. --Smokefoot (talk) 02:36, 8 July 2014 (UTC)

Support for Chemical table files[edit]

As of now, images of structural formulas have to be created using third party software and converting the output to SVG or PNG. With MolHandler we aim for a solution capable accepting and rendering chemical markup files and providing a web-interface for easily creating, modifying and re-mixing formula files. This does not only make re-using existing structures easier and simplifies creation of structures, moreover it allows Wikis to adopt a unified style for rendering these structures, makes structures searchable (sub-structure search) allows pulling, pushing and verifying data from big databases like ChemSpider and PubChem. In the future we plan to enable support for spectra and more sophisticated file formats to have at least some minimum support forchemistry-related Wiki-works.

I am currently looking for features you would find helpful as well as your opinion of what is needed to deploy MolHandler to Wikipedia and therefore created a test wiki at which you can create user accounts (and do everything you ever wanted to do). A non-exhaustive list of features is available for raking by drag&drop. Or just write here what you at least want, what you would like to see soon and what is less important to you.

TLDR
If you want to upload MOL or RXN files instead of SVGs and PNGs in future, go to http://mol.wmflabs.org/, test and say, "YES to MolHandler"!

-- Rillke (talk) 13:00, 8 July 2014 (UTC)

  • This sounds promising. To report issues at bugzilla is too much trouble. Can we have a talk page on the mol Wiki to discuss the experiences? Graeme Bartlett (talk) 23:12, 8 July 2014 (UTC)
    • Of course. Thanks for your error report. Also note that I may delete stuff from MolWiki and migrate it to Bugzilla or Phabricator to be able to keep track of everything (Mailinglist threads and RfCs on other Wikis are running as well, in case you are wondering why). -- Rillke (talk) 11:14, 9 July 2014 (UTC)

Wikipedia talk:Articles for creation/Asymmetric Keck Allylation[edit]

Dear chemists: This old AfC submission will soon be deleted as a stale draft. Is this a notable chemistry topic? The text seems polished in a way that makes me wonder if some of it has been taken from a book or journal article. —Anne Delong (talk) 20:41, 8 July 2014 (UTC)

  • Organostannane addition possibly deals with the same reaction V8rik (talk) 21:59, 8 July 2014 (UTC)
  • Reasons given for rejection dubious. No wonder we rarely get to see new chemistry content. V8rik (talk) 22:04, 8 July 2014 (UTC)
  • Allylation is only a redirect to a small entry in Allyl, where a single asymmetric methodology is mentioned (but not Keck's). I could easily see having a real Asymmetric allylation article (there are multiple variants) and/or Keck allylation (it seems to be a standard Name reaction). I'm not sure the intersection of those two is sufficiently notable for a stand-alone article and this AfC does seem to need a lot of work to focus on its topic, but it surely seems like a viable starting point even if it eventually would get merged or distributed somewhere else. I agree with V8rik's thoughts about the rejection itself and a possible effect of it. DMacks (talk) 22:28, 8 July 2014 (UTC)
I agree with V8rik that the reasons for rejection of this draft are dubious. It would be a shame for this article to be deleted, so I have moved it to asymmetric Keck allylation. As DMacks notes, it may be better as a part of broader topic such as allylation. Please feel free to rework, merge, etc. the content as you see fit. But for now, at least it is saved from deletion. -- Ed (Edgar181) 22:36, 8 July 2014 (UTC)


  • To find other articles about chemistry that are sitting in Articles for Creation, try typing the word chemistry into this search box:

Those with a grey box at the top have never been submitted; those with a yellow box are currently waiting review; those with a pink box have been declined. Those with a darker pink bar across the middle of the box are abandoned and facing deletion, but this deletion is delayed for six months if even one edit is made. Please don't edit ones that you think should be deleted, but if you see an abandoned one that looks viable, feel free to fix it up. —Anne Delong (talk) 04:11, 9 July 2014 (UTC)

Anne has done a terrific job bringing these new articles to our attention and asking for comments, which many of us have made. Looking through the 150 more recent "articles for creation," almost all are requests for biographies. The following is a list of chemical topics, several of which have already gotten comments thanks to Anne's efforts.

--Smokefoot (talk) 11:44, 9 July 2014 (UTC)

  • Thanks, Smokefoot, for doing the sifting. I notice that this one has had its AfC template removed, and is just sitting there going nowhere, so maybe someone would like to take a look at it. —Anne Delong (talk) 12:48, 9 July 2014 (UTC)
Looks like The aza-Cope rearrangements is a live page created by the same editor just after he stopped doing extensive work on Wikipedia talk:Articles for creation/aza-Cope rearrangement ("this one"), so the draft can probably be deleted. As with many presumable student works, this looks like it needs a bunch of work to be something more usable by non-experts, and general MOS. DMacks (talk) 14:19, 9 July 2014 (UTC)
I moved The aza-Cope rearrangements to the title aza-Cope rearrangement, merged the editing history from the AFC, and redirected the AFC to the article. -- Ed (Edgar181) 17:51, 9 July 2014 (UTC)
  • Hi Anne, thanks for the effort and thanks for mobilizing the chemistry community V8rik (talk) 16:54, 9 July 2014 (UTC)
I moved Phenacene and Azaspiracid to mainspace and did a bit of cleanup on each. -- Ed (Edgar181) 17:51, 9 July 2014 (UTC)
Hey, this is great! Watch for a similar thread in the future about the ones in the new "Draft" namespace. —Anne Delong (talk) 01:03, 10 July 2014 (UTC)

Editor conflict at Steroid[edit]

@User:Boghog, please state your argument here, that the steroids article should be moved away from IUPAC and NLM Mesh inclusion of secosteroids, to a different definition. Note to readers, this is raised here because Bohog has strongly edited current text at the foundational Secosteroid stub, essentially reverting my earlier work, and in so doing changed the direction of the Secosteroid and ultimately the Steroid article — this despite (from Talk at Steroid) knowing he did not have consensus. The Steroid article cannot both proceed with, and without the seco-, nor-, and homosteroid classes included, and the opening lede secosteroid definition at Secosteroid is the first step in redefining the content of the Steroid article. Hence, the lede definition question is a central to the direction of the Steroid article. It also has implications for nor- and homosteroids, and aza-/oxa and other categories included in IUPAC, Dictionary of Chemistry, Nat Prod Reports, and other classic sources not sympathetic with the "secosteroids not steroids" initiative. The underlying issue appears -- based on Talk at steroid -- to be that Boghog only wants only tetracyclic structures included in the Steroid article.

Boghog, discussion to you. And I ask you again, belay your impatience to change the Secosteroid and Steroid articles immediately (because you are angry with me over the nat products article, or whatever). Please do not revert and disrupt the Secosteroids and Steroids articles as they are (regarding Secosteroid inclusion), until we can reach consensus, including hearing voices from this and other projects. (I have posted a brief notice at Pharmacology; feel free to post the question in other venues as well.) Le Prof Leprof 7272 (talk) 23:23, 15 July 2014 (UTC)

Do I now see it correctly, Leprof 7272, that you are busy changing the articles over (without prior discussion), and that Boghog has reverted that because they disagree with that? --Dirk Beetstra T C 03:32, 16 July 2014 (UTC)
Dirk, in separate, full answer to your question, the backstory is as follows. When I edited the Secosteroid article lede back in early May—an article which had see no attention from anyone in many, many months—I did so because the lede did not reflect the definitions appearing in the IUPAC, IUBMB, NLM, and more specific journal (Nat Prod Reports, J Nat Prod, Steroids) categories and coverages. These coverages speak of the subcategories of steroids (seco, nor, homo, hetero) as just that, subcategories of steroids, and not as compounds similar to them. I therefore made the change in May. There was really no one there to discuss this with, but, if you look at Steroid Talk, [12], you will see that every significant change I made there was accompanied by a Talk discussion section, asking input at times, or at least explaining the course of the editing. Note, I was brought to the Secosteroid article after beginning to add seco-, homo-, and nor- material to the Steroids site, and realizing there was a disparity in definitions between the two sites (see this material, [13]).
The edit to return the definition to "similar to" was then made mid July by Boghog, immediately following a discussion in Talk at Steroid. It seems clear from that discussion and his subsequent change of the Secosteroid language to "is similar", that the eventual aim is to move Steroid from covering all these subcategories, to just covering the largest tetracyclic 6-6-6-5 tetracyclic structural class. As I argue at Secosteroid talk, this defied all of the solidly sourced, broadly accepted categorizations and source coverages indicated above. If you want something on azasteroids, you go to steroid journals. If you want to name a secosteroid, it is in the IUPAC/IUBMB nomenclature article for steroids. If you are curious about a particular nor- or homo- or seco- steroid, you can find it in the venerable 2 vol Dictionary of Steroids. That some online medical dictionaries use language indicating "derived from" is immaterial because subcategories of steroids routinely derive from other subcategories. That other online medical sources use "is similar" language is worth mentioning, but should not trump IUPAC, IUBMB, and standard usage where seco-steroids are a subcategory in the whole of the steroid category (alongside homo-, nor-, hetero-, etc.). That about.com says otherwise does not sway me, nor does attempting to interpret the NLM definition for steroids to exclude the secosteroids persuade, when the NLM Mesh overtly lists secosteroids as a subcategory of steroids. As I state at Secosteroid Talk, the desire for pedagogic simplicity and a few stray web dictionary definitions cannot trump the preponderance of usage in the major secondary sources and society and nomenclature tomes.
This is an important guiding question, hence the revert (something I have only done a handful of times here), and hence the request for broad participation. The issue is which understanding will guide the development of the Steroid article (which currently parallels the definition in place, [14], prior to Boghog's edit of this week). Le Prof Leprof 7272 (talk) 06:52, 16 July 2014 (UTC)
The proper place is to discuss this in on the secosteroid talk page, not here. In answer to Dirk's question, an older version of the article stated "a secosteroid is a molecule similar to a steroid but with a 'broken' ring". Leprof changed that to a secosteroid is a subclass of steroids. I subsequently restored the introductory sentence and added "Secosteroids are variously defined as a subclass of steroids or derived from steroids" with reliable sources to back both definitions. Then Leprof reverted my changes. There is a related discussion here. Boghog (talk) 03:56, 16 July 2014 (UTC)
Boghog has requested that the discussion take place here: [15], and I do not disagree. Le Prof Leprof 7272 (talk) 06:52, 16 July 2014 (UTC)
  • If the discussion started on that page then it should continue on that page. Otherwise it becomes fragmented and the eventual conclusion may get lost in the archives of this page... and if that happens we may end up having the same discussion some years later, when someone finds a half finished conversation on the article talk page and tried to finish it. Such things have happened before. Project Osprey (talk) 08:24, 16 July 2014 (UTC)

Borderline hydrides[edit]

Does anyone else see the issues with this article? It looks like a poorly written essay, with a confused subject. It looks like a random assembly of hydride statements, which after reading, I still don't know what defines a borderline hydride. The alternative definition covers something entirely different, which seems to be only semantically related. Is this article fixable, or should we look at scrapping it? Plasmic Physics (talk) 01:02, 28 July 2014 (UTC)

The term "borderline hydrides" appears in a handful of books - but mostly as descriptive English, rather than as a defined term. I can find almost no mention of it in journals, so it sounds like OR to me. That said, I like the idea of using dissociative chemisorption as a means of identifying covalent hydrides. We’ve had a lot of difficulty defining the bonding in transition metal hydrides, but presumably any that can form purely by exposure to hydrogen (under normal conditions) must be largely covalent? Project Osprey (talk) 08:53, 28 July 2014 (UTC)
It is not correct that hydrides formed by simple exposure to hydrogen must be covalent, that forms interstitial hydrides, if anything. How did you get that from the article in any case? Plasmic Physics (talk) 11:44, 28 July 2014 (UTC)
Shriver and Atkins, a popular inorganic text in the US and UK, uses the term "intermediate hydride" to describe the derivatives of zinc and copper. Greenwood and Earnshaw, which is more scholarly (more detailed, less of a textbook) classify hydrides as "customary to group the binary hydrides ... ionic, metallic, covalent, polymeric, and “intermediate” or “borderline"" but in the next sentence say that this classification "is unsatisfactory because the nature of the bonding is but poorly understood in many cases ... classification obscures the important point that there is an almost continuous gradation in properties - and bond types.." One recommendation might be to convert the article into a sort of disambigution page directing readers to copper hydride and zinc hydride.--Smokefoot (talk) 13:07, 28 July 2014 (UTC)
I don't know, that does not make a very strong case. That said, I like the idea of converting it into a disambiguation page, although, instead directing to Hydride and Dihydrogen complex. This could be accompanied by merging the contents of Borderline hydrides with those articles. Plasmic Physics (talk) 10:49, 2 August 2014 (UTC)

Wikimedia UK and the Royal Society of Chemistry to recruit Wikipedian in Residence - applications welcome[edit]

Dear all,

It may be of interest that the Royal Society of Chemistry, an organisation based in Cambridge and London, UK, is looking for a Wikipedian in Residence to deliver a six month full time project. The application closes on 17th August. I hope those of you interested in helping in this project will be encouraged to apply. Details are here.

Many thanks, Daria Cybulska (WMUK) (talk) 15:53, 28 July 2014 (UTC)

Wikipedia talk:Articles for creation/NAGly[edit]

Dear chemistry experts: Is this old AfC page about a notable topic? Should it be kept instead of being deleted as a stale draft? —Anne Delong (talk) 13:43, 29 July 2014 (UTC)

Thanks for the notice. I cleaned it up a bit and moved it to article space. -- Ed (Edgar181) 12:30, 31 July 2014 (UTC)
Great! I see that you made a NAGly redirect, too. —Anne Delong (talk) 03:48, 1 August 2014 (UTC)

Wikipedia:Articles for deletion/Cyclomethane[edit]

There is a chemistry-related AFD that may interest members of this WikiProject: Wikipedia:Articles for deletion/Cyclomethane. ChemNerd (talk) 11:49, 31 July 2014 (UTC)

Norleucine RM[edit]

Hi. Any input at Talk:Norleucine#Requested move would be appreciated. Cheers, Jenks24 (talk) 11:50, 31 July 2014 (UTC)

Hydronium is an Oxycation and technically CO is as well[edit]

Oxycation means positive charge on oxygen. Oxygen hates this which is why hydronium is an ion in a complex of ions which itself is in a complex of ions and so on and so forth is so that the positive charge is spread instead of localized to 1 oxygen atom.

Hydronium is H3O+ and the positive charge is on the oxygen.

3 bonds + 1 lone pair = +1 charge on oxygen

CO has this as well because of the 2.5 bond and so despite the oxygen being more electronegative it is positive and the C is negative because of this:

3 bonds + 1 lone pair

for carbon this means a -1 charge and for oxygen it means a +1 charge

The fact that it is the oxygen that is positive in both of these cases makes them oxycations. Caters1 (talk) 12:57, 31 July 2014 (UTC)

This is not the place to speculate. We work on sources. However, you will not find a source that says that CO is an oxycation, because it is not. To be an oxycation it has to be a cation. To be a cation, it has to be an ion and CO is not. Also the O in CO is not that -ve. The dipole moment is quite small. --Bduke (Discussion) 20:54, 31 July 2014 (UTC)
To be an ion, the species must, by definition have an overall charge. Carbon monoxide lacks this key quality. Plasmic Physics (talk) 21:07, 31 July 2014 (UTC)
CO has a 2.5 bond which makes there be a positive charge on the oxygen since it is the O's lone pair that is used to form the bond while the C's lone pair stays there. Thus the carbon becomes negative(-1 formal charge, not partially negative) and the oxygen has a +1 formal charge which it hates.
Thus while it is neutral overall to be an oxycation it does not mean the whole molecule has to have a positive charge. Oxycation literally translates to "Positively Charged Oxygen" which is all it means.Caters1 (talk) 02:00, 1 August 2014 (UTC)
Carbon monoxide has a fairly established triple bond. But let's step back...what's your point here? Yes, the O of CO has a formal charge of +1. No, nobody here really cares about specific identifying terms for it unless a reliable source says so. No, the oxygen is not actually a +1 ion (bond polarization counteracts it), and the molecule is not nearly as polar as the formal charges would suggest. DMacks (talk) 04:04, 1 August 2014 (UTC)
Actually, that is incorrect. Even if 'oxycation' is literally translated (despite it already being in english), that is not its definition. An oxycation is any cation which contains oxygen, and does in fact require an overall charge on the species. Plasmic Physics (talk) 06:15, 1 August 2014 (UTC)
Chemists always talk about it in terms of formal charge and when they say oxycation, they don't necessarily mean positively charged molecule with oxygen. In fact this is an uncommon definition in chemistry, especially organic chemistry. Instead they more often mean instead of a +1 ion with oxygen, a molecule that may or may not be neutral but has a positively charged oxygen.
CO has 2 resonance structures that follow the octet rule and 1 that doesn't. They are these [:C=O(with 2 lone pairs on the O) <-> -^:C-=O:^+(which follow the octet rule) and <-> +^:C-O^-(with 3 lone pairs of electrons that doesn't follow the octet rule)]
The one with a triple bond has a carbanion(negatively charged carbon) and an oxycation(positively charged oxygen). The one with the single bond has a carbocation(positively charged carbon) and an oxyanion(negatively charged oxygen). All of these are based on formal charges and not partial charges caused by polarity. The carbon in CO always has 1 lone pair of electrons. There is no case where the double bonded one is like this (0 lone pairs)C=O(with 2 lone pairs) as this would make carbon have a +2 charge which is even more unstable than a +1 charge for something not so electropositive. Carbon isn't so electronegative either, especially compared to hydrogen where there is like a .04(maybe .4) difference and so it is at best mildly polar those hydrocarbons and also a -2 charge would be even more unstable for carbon than a -1 charge because of this.Caters1 (talk) 19:09, 1 August 2014 (UTC)
[(:)C]=[O(::)] is not octet stable (it only follows the strict "don't exceed octet" part, not the "meet octet" maximal stability part). It's closer but still non-compliant in the same sense as +[(:)C]–[O(:::)]+ is non-compliant. But once you're just making up things as you go along, you would need to consider all sorts of octet-deficient and multiply-charged cases rather than only the "most likely/reasonable" ones in your analysis. Again again, nobody is disagreeing that CO has a formal O+1 and that this is an atom that is cationic, and nobody seems to be willing to change their opinion of the definition of contracted term "oxycation". Unless you or someone else wishes to raise a new point, I agree that this section should (and probably should have a while ago) be hatted so we don't spend more time not-writing-an-encyclopedia. DMacks (talk) 20:29, 1 August 2014 (UTC)
I have watched organic chemistry videos and when they say -cation they mean positively charged atom so carbocation = positively charged carbon, not positively charged molecule that contains carbon. They say similar things for carbanion, oxyanion, and oxycation with -anion meaning negatively charged atom, not molecule. Some inorganic chemists say the same thing and so would agree with my statement that CO has in the resonance structure with a triple bond a carbanion and an oxycation. The sites where I have watched these organic chemistry videos that say carbocation = positively charged carbon, carbanion = negatively charged carbon, oxyanion = negatively charged oxygen, and oxycation = positively charged oxygen are Youtube and Khan Academy, with Khan Academy being more reliable.Caters1 (talk) 21:24, 1 August 2014 (UTC)
https://www.khanacademy.org/science/organic-chemistry/organic-structures/formal-charge-resonance/v/formal-charge-i says that carbocation mean positively charged carbon atom within a molecule and carbanion means negatively charged carbon atom within a molecule.
https://www.khanacademy.org/science/organic-chemistry/new-topic-2014-06-13T19:24:28.593Z/formation-of-enolate-anions/v/enolate-formation-from-aldehydes and
https://www.khanacademy.org/science/organic-chemistry/new-topic-2014-06-13T19:24:28.593Z/formation-of-enolate-anions/v/enolate-formation-from-ketones both say that an oxyanion is a negatively charged oxygen atom within a molecule(just like with the carbocation and carbanion the overall charge on the molecule could be positive, negative, or neutral).
By this logic oxycation should mean positively charged oxygen atom, not positively charged molecule that contains oxygen. Caters1 (talk) 18:29, 11 August 2014 (UTC)
And both :C=O(::) and :C-=O: are octet stable. Why? The O has an octet in both cases. C can have less than an octet and that doesn't matter. O can't really have less than an octet though even when talking about a peroxide bond which is why an alkoxide has 3 lone pairs of electrons on the O. This is also why the single bond resonance structure of O2 has 2 negatively charged oxygens both with 3 lone pairs of electrons (:::)O-O(:::)
Your single bond resonance structure of O2 dies not exist, You show 14 valence electrons, not 12. It is O22-. I want to make a general point. The term oxycation or oxyanion can not be used just because one resonance structure is +ve or -ve, unless that structure is dominant. The use of these terms also has to be backed up by experimental information. It is not appropriate to use the terms for CO because the dipole moment of CO is extremely small. It is not a polar molecule. --Bduke (Discussion) 21:10, 25 August 2014 (UTC)

C2O4[edit]

Here is another possible structure for C2O4:

CO2-O-C=O

The CO2 that is bonded to an oxygen looks like this:

[O=C-O <-> O-C=O]

the O is bonded to 2 carbons.

There is both an oxyanion and a carbocation in this isomer of C2O4.

The negatively charged oxygen reacts with the positively charged carbon and a ring with alternating carbonyls and oxygen atoms forms.

Another possibility is that the O is single bonded to an O and a C which would mean that it is straight.

It looks like this:

O=C-O-O-C=O

there are no oxyanions this time but there are now 2 carbocations instead of 1. This could be stabilized by adding H2 to it or more likely the O-O bond will break and form 2 CO2 molecules and there is even a possibility of the single C-O bonds breaking leaving O2 + 2 CO. — Preceding unsigned comment added by Caters1 (talkcontribs) 13:07, 31 July 2014 (UTC)

This is not the apppropriate place for this kind of thing. I'm not sure that anywhere on Wikipedia is. I think we should probably delete this section and the preceding one, or put it in a collapsed hat template. 0x0077BE [talk/contrib] 13:11, 31 July 2014 (UTC)
This I feel is the right place, especially for the one about hydronium being an oxycation. You or some other people could edit the hydronium article to say that it is an oxycation and add both of my structures for C2O4 and information about it including stability and possible bond breakages to the C2O4 article you already have.Caters1 (talk) 14:50, 31 July 2014 (UTC)
Again, we rely on reliable sources. Nobody is going to add your structures unless they are discussed in a reliable source. When writing here please link the articles you refer to, such as C2O4. --Bduke (Discussion) 21:01, 31 July 2014 (UTC)
I honestly looked at the molecular formula and looked at possible structural isomers of https://en.wikipedia.org/wiki/C2O4 that you didn't already have on there and I came up with ones that have single C-O bonds that are not between a carbonyl in a ring and an O but rather a C and an O(and for one of them 2 O's) along with the resonance structures for it and even possible intramolecular reactions and bond breakages.Caters1 (talk) 02:09, 1 August 2014 (UTC)
Let's be very clear. Wikipedia articles (and editors writing them) are absolutely prohibited (WP:SYNTH is the main policy) from including our own hypotheses or personal analysis/extrapolations. There are probably dozens of isomers one could draw for C2O4, especially if one doesn't care about octet rule or other electronic or structural stability details. But unless there are reliable published sources that make the case for them (even if only as a computational analysis for why they would be hard to make), they have no business being listed on the C2O4 page. It's a great mind game (and intro organic-chemistry exam question) try to draw as many "likely to be stable" isomers for a given formula as possible. DMacks (talk) 04:13, 1 August 2014 (UTC)
Support DMack's comments that one needs "reliable sources". I would add that articles are far stronger if they have a foundation of secondary sources, per WP:SECONDARY. We are mainly looking for topics that have been the subject of a review or discussed in books, usually textbooks. In this way, the article almost automatically meets notability standards and editors avoid synthesis.--Smokefoot (talk) 04:37, 1 August 2014 (UTC)
For the record, SciFinder lists two additional structural isomers of C2O4 (each having various peroxide bonds in one or more rings) restricting to those that are octet-stable and zero net charge (these also happen to have all zero formal-charges). And then additional ones if net charge ≠0 is allowed. And I can even envision even more (based on known functional groups, just not on this particular substrate) that also are net-zero (and more that are not). But that just proves that reliable sources trump our brainstorming (and demonstrates why only the former is allowed for our encyclopedia). DMacks (talk) 21:48, 1 August 2014 (UTC)
but my straight one has a peroxide bond. O=C-O-O-C=O. This could then form a 6 membered ring by forming another peroxide bond from the pi bonds(however this is unlikely). You could then add 2Hs to each carbon to make it have an octet and 0 formal charge. You would then have C2H2O4 in the form of a ring with 2 peroxide bonds. This is an isomer of oxalic acid like how the straight chain with 1 peroxide bond is an isomer of C2O4. I can only think of 2 acyclic isomers of C2O4 so that means the rest of them must be 3 membered rings, 4 membered rings, 5 membered rings, and 6 membered rings. You have 2 of the 4 membered ones. 5 membered and above always have at least 1 peroxide bond in the ring whereas 4 membered and below don't always have peroxide bonds.Caters1 (talk) 15:11, 2 August 2014 (UTC)
Your straight one is original research and by Wikipedia policy is strictly forbidden. Unless you can supply a reliable source that documents its notability, it has absolutely no place in Wikipedia. Full stop. Boghog (talk) 17:22, 2 August 2014 (UTC)

Fulminic acid[edit]

It seems to me that the right-hand half of this diagram is wrong - the electrons do not add up. It would make since if there ewer a double bond between N and O, a negative charge on the C, a positive charge on the N, and no charge on the O. But it's over 40 years since I studied chemistry, so I'ld like another opinion before I alter it. Maproom (talk) 11:40, 1 August 2014 (UTC)

I get an electron count of 16 every time: 1+4+4+7, 1+3+5+7. Plasmic Physics (talk) 12:27, 1 August 2014 (UTC)
I agree. There is an implicit lone-pair on the N in the right diagram (the reaction mechanism for converting left to right is that one of the three pairs shared between C and N pulls back to being solely on N). Seeing the charges is enough explicit detail to determine presence of those non-written electrons. The same analysis is how we know each O actually has 3 implicit lone-pairs (otherwise, each would be +5 not –1). I don't see this mentioned in our skeletal formula, formal charge, or lone pair articles? Yikes! DMacks (talk) 20:38, 1 August 2014 (UTC)

Hydride compound article names[edit]

I recommend that some of the hydride compound articles be moved, for either one, or both of two reasons: firstly, to specify stoichiometry, and secondly to place emphasis on the status of the hydride as the standard state. For instance, since Diborane is the standard state, saturated boron hydride, it could be moved to Boron(III) hydride. This name is suggested by IUPAC nomenclature recommendations as true to stoichiometry and structurally neutral. An alternative is name that also conforms to the same criteria is Boron trihydride. However, I would dissuade from using this name to preserve the existing naming style of similar articles, which is employing oxidation states.

Articles that would be affected by this motion are the following:

Plasmic Physics (talk) 10:11, 2 August 2014 (UTC)

I strongly disagree about the two compounds I do know something about - Diborane and Digallane. These names are the most common and link to the actual structure, whereas Boron(III) hydride and Gallium(III) hydride suggest that the structures are BH3 and GaH3. I suggest you leave well alone. --Bduke (Discussion) 11:21, 2 August 2014 (UTC)

The issue is whether most readers will know to search for Diborane or Digallane when looking for boron's and gallium's standard saturated hydrides. I can assure you that by established definition, 'Boron(III) hydride' and 'Gallium(III) hydride' make no such suggestions concerning structure. Plasmic Physics (talk) 12:28, 2 August 2014 (UTC)
A compromise could be the following:
Plasmic Physics (talk) 12:47, 2 August 2014 (UTC)
In general article names which imply stoichiometry only become important when a number of stoichiometries are possible (e.g. Iron(II) chloride and Iron(III) chloride), I'm not sure this applies for most of these. I don't suggest this out of a mischievous disregard for IUPAC, the reason is practical: Wikipeadia searches primarily work by finding page names and people are lazy - they'll enter the simplest search terms there are. Using common and non-technical names for pages increases the chances of people finding what they want. The pages themselves are where things like stoichiometry should be made clear. Seen through that lens I agree that Boron hydride should be converted to a disambiguation page directing to Boranes, Diborane, Borane and category:Boranes. Likewise Beryllium hydride should become a disambiguation page directing to Beryllium monohydride (as Beryllium(I) hydride) and Beryllium(II) hydride. Project Osprey (talk) 16:05, 2 August 2014 (UTC)
I do disagree as well. Again, we do not aim to have the article at the (IUPAC-)correct name, we aim at having the article at the common name as 'the public' would know it. This is similar to the discussions earlier (and I thank you for bringing them up here). Many of these compounds are simply known by more common names, or where the IUPAC name is overly precise (beyond what our goal is here). Especially diborane is one of those cases (but the others as well). E.g. Zinc chloride, diethylzinc .. see all the compounds in Category:Zinc_compounds .. the only one that is at 'Zinc(II) XXX' is actually the one you propose to move here, Zinc(II) hydride, but which you personally moved back in January 2013 (and I would suggest that it gets moved back to Zinc hydride). I would look in a chemical catalogue for 'Zinc hydride', I would ask collegues for 'Zinc hydride', I would not even consider to ask for 'zinc two hydride' (and that goes for most of these, the common oxidation state for all of these is the one used for the main article, if 'zinc(I) hydride' is notable and exists (probably this is a fictional example), then the article Zinc(I) hydride can be created, and then still there is no issue with having two names which do not fully line up with each other, the common Zinc hydride (with the common, +2 oxidation state) and the uncommon Zinc(I) hydride (with the uncommon +1 oxidation state and hence the oxidation state notification).
Please, Plasmic Physics, do not aim to follow IUPAC like this, please take that out of your mind. It is against our manual of style. I am sorry, but there is no consensus for the strict following of IUPAC in naming (and that reasoning goes up our Manual of Style: "A title should be recognizable (as a name for or description of the topic), natural, sufficiently precise, concise, and consistent with the titles of related articles", 'sufficiently precise', not 'precise'), and for many cases it results in original research (not for these simple binary compounds probably, but when the compounds get more complicated, it needs an interpretation of the IUPAC rules beyond 'simple mathematics', see the alkene discussion with user User:Andrewa of some time ago - you really need to know what one reads and how to use them). I suggest, as per Smokefoot below, that you (and probably most editors) stay away from these precise nomenclature and naming issues and just use common names, or leave them as is. --Dirk Beetstra T C 06:27, 3 August 2014 (UTC)
I honestly feel like I'm repeating myself, this has nothing to do with following IUPAC nomenclature. Can everyone please stop changing the subject. Plasmic Physics (talk) 06:52, 3 August 2014 (UTC)
So, now explain me why you chose the name 'Boron(III) hydride'? Where did you get that name, and why do you think the article should be moved there? Do you think that the use of 'Boron(III) hydride' is more common than the use of the term '(di-)borane'. Actually, that one is funny, since below you suggest to move Mercury(II) hydride to mercurane(2) ('.. for the sake of conformity, ..'). And by the way, you started of with 'This name is suggested by IUPAC nomenclature recommendations as true to stoichiometry and structurally neutral' - that is not a change of subject if I then say, again, that we do not follow IUPAC like that, we have our own Manual of Style which describes different naming rules, and that was exactly why I said that. Moreover, it results in original research problems. Please, stop precise nomenclature and naming issue discussions. --Dirk Beetstra T C 08:07, 3 August 2014 (UTC)
I coincidently used the IUPAC recommendations to construct the name 'Boron(III) hydride', for lack of knowledge of an alternative nomenclature system that can be used to construct ordered names. Do you know of an alternative nomenclature system? If so, I'd be happy to investigate it. I already addressed your question in the lead, regarding why I think it should be moved. It has nothing to do with the commonality of a name, it is for practical reasons. If a reader does not know that diborane is the standard structure with the empirical formula BH
3
, then the suggested move will automatically redirect them to the correct article. I can't help but notice that you didn't take into account my suggested compromise. I direct you to the five guidelines of WP:Article titles. Note the fifth guideline regarding consistency. They are guidelines, and so it is perfectly acceptable for one to override the ideal of commonality, if pursuing the ideal becomes a liability rather than an asset to the reader with an amateur foreknowledge. Almost every guideline can be used to justify the proposal. Although, I suppose that the argument is how strongly. Plasmic Physics (talk) 11:30, 3 August 2014 (UTC)
Well none of the above should be moved as explained by the others. The policy takes precedence over the guidelines, and that is the use of the common name. You can create redirects for all those suggested names, but please do not move them. Some day I will write an article on MgH gas, it is almost always referred to as MgH in the literature, but we can give it a longer more official name as long as it is actually the common name for the substance. However what is called magnesium hydride is always MgH2. Magnesium(II) hydride is rarely used as a term. Graeme Bartlett (talk) 11:50, 3 August 2014 (UTC)
For clarity, where does it say that policy trumps guidelines? Using your own example, there is revealed a flaw - "Avoid ambiguous abbreviations" - WP:AT. MGH already exists, and MgH is also known as 'magnesium hydride'. Plasmic Physics (talk) 12:05, 3 August 2014 (UTC)
P.S. Regarding the overriding of commonality: "If it exists, choose an alternative name that the subject is also commonly called in English, albeit not as commonly as the preferred-but-ambiguous title." - WP:AT. Plasmic Physics (talk) 12:40, 3 August 2014 (UTC)
Take a look at Wikipedia:Policies and guidelines. Just because something is ambiguous does not mean that we have to avoid using the name, especially when one use is far more common than other uses. It is when the different uses are roughly as likely that we need to chose names that will distinguish them. Otherwise the common use get the name, and a hat note will help you find the other use or uses, possibly via a disambiguation page. In some cases it makes sense to have an article on the family of compounds, which would be possible for hydrides of an element. I still support the existence of redirects for official names to the common name. Also there should be redirects for formulas. I am not sure why MgH redirects to MGH. But there is no article or writings on magnesium monohydride yet, so readers have no reason to complain. Graeme Bartlett (talk) 23:58, 3 August 2014 (UTC)
Where in WP:AT does it draw the distinction? Plasmic Physics (talk) 00:17, 4 August 2014 (UTC)
Just around what you quoted above. Primary topics and such. --Dirk Beetstra T C 05:51, 4 August 2014 (UTC) I am moving the Thallium hydride part to a new subsection below, needs a bit of different discussion
Can we at least agree on the compromised proposal for boron, and gallium, if not for the remainder; and a hat note for beryllium? Plasmic Physics (talk) 21:29, 4 August 2014 (UTC)
The redirects for boron and gallium are cheap (and I would not really oppose that all the redlinks here are converted to redirects) .. the hatnotes I am really not sure, per WP:UNDUE. --Dirk Beetstra T C 03:28, 5 August 2014 (UTC)

Miscellaneous moves[edit]

While not necessary to address the aforementioned issues, for the sake of conformity, Beryllium monohydride and Indium trihydride could also be moved to Beryllium(I) hydride and Indium(III) hydride, respectively. Furthermore, Mercury(II) hydride does not require a structurally neutral name, also for the sake of conformity, I thus suggest moving it Mercurane(2). Plasmic Physics (talk) 10:11, 2 August 2014 (UTC)

Plasmic, first of all, thanks for asking about some of your thoughts on renaming. My advice is that you avoid issues of nomenclature. Recent initiatives on nomenclature has kicked up a lot controversy and has sucked up too much effort on the part of editors, you included, who could be contributing high level content in other areas. --Smokefoot (talk) 13:46, 2 August 2014 (UTC)
There is a subtle difference here. While a related topic, the issue regards article naming, and is of a practical nature. It is not about something as relatively trivial as simple nomenclature within the article space. Although, I suppose that it will have to be updated after the moves to reflect the new article names. Plasmic Physics (talk) 14:16, 2 August 2014 (UTC)
See above. For Mercury(II) hydride, since Hg(I) and Hg(II) are both quite common (both Mercury(II) hydride and Mercury(I) hydride exist), here the indication is necessary. I oppose strongly against Mercurane(2) as the name for the article, again, that is far, far from the common name. --Dirk Beetstra T C 06:27, 3 August 2014 (UTC)
Really? Can you cite that it is most common? Plasmic Physics (talk) 06:52, 3 August 2014 (UTC)
It strikes me as highly unusual that such an esoteric compound, which has only been known for barely a decade, would already have a most common name. Plasmic Physics (talk) 07:37, 3 August 2014 (UTC)
Well, Mercurane(2) is the .. IUPAC suggested name, I would however look for .. mercury hydride (and then figure out there is mercury(I) hydride and mercury(II) hydride .. ). Just like I would look for sodium hydride, beryllium hydride, aluminium hydride, phosphane and borane .. As per my suggestion above, if the article was created as Mercury(II) hydride, then the editor doing that found that the .. more common name. Please leave the renaming, naming issues etc. alone. --Dirk Beetstra T C 07:56, 3 August 2014 (UTC)
Not necessarily - the creator may have simply synthesised the name, and lacked any knowledge of the common name, which seems the more likely explanation when taking into account the circumstances of the article's origin. Plasmic Physics (talk) 10:58, 3 August 2014 (UTC)
Let's ask User:Whoop whoop pull up to comment on that, and whether they lack that knowledge. All I see that you went into a near edit-war with the editor about a section in this article where you added unreferenced material which they removed again, and later, when you added references, added references which were found to be dubious. Later that whole section was again wholesale removed due to the lack of references capable of supporting the material that you added. I don't know how likely that lack of knowledge on their side is. --Dirk Beetstra T C 11:30, 3 August 2014 (UTC)
[16]. From what I remember, the article was created in haste, and out of spite over a content dispute. Plasmic Physics (talk) 12:49, 3 August 2014 (UTC)
Whatever, you asked for opinions on the namechange, you've got mine and maybe others will comment as well - that article name is just fine. My suggestion however is still, leave naming discussions alone, Plasmic Physics. --Dirk Beetstra T C 03:49, 4 August 2014 (UTC)
And if there is no 'more common' use of either of them, then there is no reason to move either, we leave it at the place where the original author, who thought that that was more recognisable, natural, sufficiently precise, consise and consistent with the titles of related articles, or even where they chose it to be. The request for citations of 'which is more common' is hence circular. --Dirk Beetstra T C 08:07, 3 August 2014 (UTC)
That reasoning is acceptable, since the suggestion was based on the idea of conformity to a common style, as stated in the lead. Plasmic Physics (talk) 10:58, 3 August 2014 (UTC)
Although our MOS suggests that conformity, it is by no means a driving force for the choice of article names - the 'conformity' at the moment is that we follow the 'common name', not one type of style systematically (and we don't have to, neither is it going to make any sense in the end as while for Mercury(II) hydride it makes sense to use this name, for Calcium hydride another naming convention makes more sense, and for diborane yet another makes more sense - making it conform to one makes sense on the small scale, but becomes useless if one extrapolates to the other extremes: Carbon(IV) hydride, Oxygen(II) hydride? Use common sense, not rules, we're never getting things to an all-over conform system as that would result in, albeit perfectly correct, impossible and completely uncommon names for articles). --Dirk Beetstra T C 11:30, 3 August 2014 (UTC)
The guidelines given above, regarding consistency specifies "similar articles", those extremes are exactly that, extremes. They certainly not similar to the same degree. Plasmic Physics (talk) 11:37, 3 August 2014 (UTC)
Besides, they would be called Hydrogen carbide(-IV) and Hydrogen oxide(-II), since hydrogen is the more electropositive. Plasmic Physics (talk) 11:40, 3 August 2014 (UTC)
The situation for Calcium hydride (vs. Calcium(II) hydride) is not that dissimilar from Water (vs. Hydrogen oxide(-II), or even ), in both cases the former is, by far, the more commonly used name. That's what our MOS suggests, that is where the article is. Although Calcium(I) hydride may exist, I would even oppose to have it named as a 'you may be looking for ..' above the lede of the article - Calcium hydride (Calcium(II) hydride) is a bulk chemical, all the other hydrides are 'rare' (and some may even lack notability on a Wikipedia level, even if they reasonably exist). --Dirk Beetstra T C 03:49, 4 August 2014 (UTC)

Thallium hydride[edit]

What about the case of Thallium hydride? The monohydride is the more stable hydride, and better known than the trihydride, yet the trihydride receives preferential treatment. Plasmic Physics (talk) 00:17, 4 August 2014 (UTC)

No, Plasmic Physics. That Thallium hydride receives 'preferential treatment' is because you rewrote the article from being about both hydrides to being about the trihydride only. Thallium hydride either probably be about the monohydride (as you suggest the more known hydride, and to my recollection, Th(I) is, reasonably by far, the more common oxidation state), and Thallium(III) hydride should be about the trihydride (but if I am wrong in that, and the Category suggests that, maybe the couple should be 'Thallium(I) hydride' and 'Thallium(III) hydride').
It is, however, not 'preferential treatment', it is about how the editing process works. Sometimes articles end up in 'really wrong' :places (you may be right about that for Thallium hydride), and then renaming, moving, splitting is an option. However, for the far majority of articles that you name in this section the name is not 'really wrong' - where for Thallium hydride my guess would indeed be 'ThH' (not ThH3), for Magnesium hydride, Calcium hydride, Aluminum hydride, Zinc hydride, and Beryllium hydride that ambiguity does not really exist, those elements have one really major preferred oxidation state that any chemist would expect it to be in (and even high school students - no teacher would teach their students to add 'sodium one sulfate' or 'calcium two carbonate', it would be 'sodium sulfate' or 'calcium carbonate'). --Dirk Beetstra T C 03:49, 4 August 2014 (UTC)
Thinking about this, as both 'Thallium(I) hydride' as well as 'Thallium(III) hydride' (could) exist (as well as maybe other binary compounds of H and Th), but none of them seem to have independent notability (they seem to be just of academic interest at the moment), maybe the article should be about the (possible) thallium hydrides in general (I do think we should have articles on all 'bulk-element' hydrides), not specifically about one of them (as it seemed to be before the changeover by Plasmic Physics). If one of them gets individual notability that can be handled by a split at that time. --Dirk Beetstra T C 05:51, 4 August 2014 (UTC)
If something doesn't have "independent notability", why does it have an article? We deal with lots of essoteric and niche topics in chemistry, but WP:GNG still is an overall site guideline. DMacks (talk) 12:52, 4 August 2014 (UTC)
Agree 100%, especially if the development of these articles is supported by flimsy sources (3rd rate journals and such), On the other hand, one salutary aspect is that this strangeness focuses on unimportant topics, vs threatening important ones. --Smokefoot (talk) 13:38, 4 August 2014 (UTC)
That is why I say that the article should turn back to be about all 'possible' hydrides of Thallium. The fact that 'they do not exist - or are at least of minor importance' is in itself notable where (practically) all other element-hydrides do exist. The article should never have specialised to a specific hydride. --Dirk Beetstra T C 03:20, 5 August 2014 (UTC)
Agree that this activity by Plasmic is ill-advised and the results are almost invariably mediocre and suffer from WP:UNDUE. Unfortunate. --Smokefoot (talk) 13:04, 5 August 2014 (UTC)

Mercury hydride[edit]

Mercury hydride is at AfD, having been nominated by user Plasmic Physics. See Wikipedia:Articles for deletion/Mercury hydride. -- 101.117.57.173 (talk) 00:09, 11 August 2014 (UTC)

I see that, after the above discussion and a discussion with User:John on their talkpage, User:Plasmic Physics unilaterally decided, following the thoughts of the discussion and ignoring the suggestion to leave naming issues alone, that Mercury(I) hydride is not as notable as Mercury(II) hydride, and that therefore Mercury hydride has to be a redirect to the, in their opinion, more common Mercury(II) hydride. When that did not stick, they decided to AfD the article. I am sorry, Plasmic Physics, but I can't decide here whether these actions are WP:POINTy, a failure to drop the WP:STICK, or WP:DISRUPTive. Can you please withdraw the AfD and from now on really leave naming and nomenclature issues alone, at least for a year or two? --Dirk Beetstra T C 03:30, 11 August 2014 (UTC)
I came into this not knowing any of the history, but looking at the arguments in this specific case, I'm not convinced that Mercury (I) hydride is not a good target for redirect from Mercury hydride, assuming that Plasmic Physics' claims about IUPAC nomenclature don't hold water (and the consensus seems to be that they don't). Mercury hydride is the systematic name for Mercury (I) hydride, according the the article, and according to the IP editor at the AfD, mercury hydride most commonly refers to Mercury (I) hydride in the literature. At the moment, I'm not sure what the disambiguation page is even adding here - most people would need to choose one of the pages at random anyway to try and figure out which hydride they are looking for anyway, since the disambiguation page only disambiguates based on the chemical formula - which is probably not going to help non-chemists disambiguate between the two, and chemists would likely find redundant anyway since the article titles are disambiguated by oxidation state anyway. 0x0077BE [talk/contrib] 03:43, 11 August 2014 (UTC)
The disambiguation page is there to show that there are two pages that 'Mercury hydride' could refer to. I don't think either has a significant significance over the other, so solutions could be to either merge the two into Mercury hydride (which may become somewhat confusing if there is enough to tell about either), or have both separated with a disambig in front of it. I do not believe there is a primary topic here at this time, I might only agree that the disambiguation could do a better job in disambiguation. I just think that this is an 'extrapolation' by User:Plasmic Physics from the naming and organisation other hydrides, where the situations are obviously different, and that that then also has to be implemented here. --Dirk Beetstra T C 06:14, 11 August 2014 (UTC)

Particulates[edit]

The uses of Particulate, Particulates, Particulate matter is under discussion, see talk:Particulates -- 65.94.169.222 (talk) 04:35, 4 August 2014 (UTC)

pertechnetic acid[edit]

i think an image for technetic(V) acid got lost 24.131.80.54 (talk) 03:40, 9 August 2014 (UTC)

Do you mean Pertechnetic acid? The revision history doesn't seem to indicate that any images were lost. Care to enlighten? 0x0077BE [talk/contrib] 03:07, 11 August 2014 (UTC)
Something is wrong with the image used in the article. File:Pertechnetic_acid.png is used in the infobox but it does not display properly for me either. ChemNerd (talk) 11:22, 11 August 2014 (UTC)
Fixed. Project Osprey (talk) 12:06, 11 August 2014 (UTC)
In the new image, File:Pertechnetic acid 3D ball.png, shouldn't three of the Tc-O bonds be double bonds, rather than only two of them? And in the old image, File:Pertechnetic_acid.png (which for some reason is displaying properly for me now when I look at the article history) is there an oxygen atom missing, or is it just hidden behind the Tc atom? ChemNerd (talk) 17:10, 11 August 2014 (UTC)
  • Actually, in the new image there are 3 double bonds; it's just hard to see because of how its orientated. No idea what was happening in the original image. I'm not actually the one making these btw, I just find them on wikimedia. Project Osprey (talk) 21:28, 11 August 2014 (UTC)
Thanks. I see now what I missed in Pertechnetic acid 3D ball.png ChemNerd (talk) 20:21, 12 August 2014 (UTC)

Chlorine Peroxide[edit]

Chlorine peroxide should be of this form: Cl-O-O-Cl but instead it redirects to O=Cl=O or chlorine dioxide. A peroxide is by definition of this form: A-O-O-A or A-O-O-B where A and B are any atom besides oxygen or flourine(F-O-O-F is Dioxygen Diflouride with each O in a +1 oxidation state). The O-O single bond is what differentiates peroxides from other oxides. Chlorine peroxide should redirect to Dichlorine Dioxide instead of Chlorine Dioxide and the infobox for Dichlorine Dioxide should be edited in the Other Names section to include Chlorine Peroxide since it is in fact a peroxide.Caters1 (talk) 01:23, 12 August 2014 (UTC)

The spirit of the redirect is to help readers vs satisfy the fastidious tendencies of chemists. Readers might think that ClO2 is a cyclic peroxide. Wikipedia would welcome an article on ClOOCl (RN 12292-23-8). Key to creating an article are WP:SECONDARY references to establish notability, and here are two reviews:
  • "Oxygen compounds of halogens X2O2(X is a halogen atom" doi 10.1070/RC2002v071n02ABEH000684
  • "UV Photolysis of ClOOCl and the Ozone Hole" DOI: 10.1002/asia.201100151

Happy editing.--Smokefoot (talk) 02:52, 12 August 2014 (UTC)

ClO2 indeed has a resonance structure in which there is a peroxide bond in the ring. However this is very unstable, more so than O=Cl=O. This is why CO2 does not exist in a cyclic form is because cyclic peroxides are unstable in normal conditions, especially ones in 3 membered rings.
Because of this, acyclic peroxides are preferred over cyclic peroxides and so chlorine peroxide would most likely be Cl-O-O-Cl. It is the free radical form of this, that is 2 Cl-O + CO2 that causes there to be the ozone hole(and not the peroxide itself) because Cl-O(chlorine monoxide) violently reacts with Ozone to form Chlorine Dioxide and O2 and CO2 is easily(more easily than O2) photolysed into CO and O(atomic oxygen) both of which violently react with the Ozone. CO reacts with O3 to form CO2 and O2(similar reaction to the one with chlorine monoxide) and atomic oxygen reacts with the Ozone to form 2 O2 molecules.
Thus because of acyclic peroxides being the prefered type of peroxide the Chlorine Peroxide page redirect is redirecting to the wrong page.Caters1 (talk) 03:07, 12 August 2014 (UTC)
Dear Caters1: recheck meaning of resonance structure. --Smokefoot (talk) 10:57, 12 August 2014 (UTC)
  • We do have an article on ClOOCl at dichlorine dioxide. I can't see anyone objecting to you changing the redirect. Project Osprey (talk) 09:18, 12 August 2014 (UTC)
  • I have made an improved page at ClO dimer using one of the suggested references that actually includes info that I can find online. I have changed redirects all round. Graeme Bartlett (talk) 10:31, 12 August 2014 (UTC)
Resonance structure means "If you move these electrons onto here and form a new bond or just move the electrons(like in forming an alkoxide from a ketone or aldehyde for instance) you get a different structure of the same molecule" Thus ClO2 has a cyclic resonance structure because you can move the pi electrons onto the oxygen atoms and form a peroxide bond to get a cyclic peroxide. It also has acyclic resonance structures much like those of CO2.Caters1 (talk) 14:16, 12 August 2014 (UTC)

Base[edit]

I am looking for more opinions on whether to call substances that can react with the naked proton a base or not. In Talk:Methylidyne radical User:Plasmic Physics considers that Methylidyne radical and even argon and helium are bases because they can react with a proton (in the gas phase). However I think we should only state that the substance is a base if other reliable sources say so. What do others think? Should every hydride that can part with a proton or accept a proton be called amphoteric with an unsourced Amphotericity section? Graeme Bartlett (talk) 11:04, 13 August 2014 (UTC)

"Naked proton" is hyper specific. Argon and helium being bases are extreme examples, which you raised to ridicule the implications of the argument. Yes, technically helium is the conjugate base of the helium hydride ion, but it is such a weak base, that its basicity is not notable. Methylidyne is not in the same ball-park; it is not a fair comparison.
The basicity of methylidyne is a logical implication of the conjugate acid-base model of Brønsted–Lowry acid–base theory, and as such, it is covered by "uncontroversial knowledge" under WP:SCICITE. The Amphotericity section describes methylidyne's ability to act as both a Lewis acid, and a Lewis base. As you all know, protonation within the Brønsted–Lowry acid–base theory is a particular type of adduction, where the hypothetical proton acts as the Lewis acid. The 'adduct' of methylidyne and a proton is known to exist. Furthermore, the section is making no speculative commentary which cannot be independently confirmed to comply with the BL theory. Another important concept is proton affinity, which specifically describes the helium hydride ion as an extreme example. Now the section does not say that methylidyne is more basic than it is acidic, only that both types of character are exhibited. Plasmic Physics (talk) 11:57, 13 August 2014 (UTC)
H+ can accept H+ in proton–proton chain reactions to give D+. Can I therefore argue that acid has Lewis basic character with a pKa of infinity? Project Osprey (talk) 12:17, 13 August 2014 (UTC)
No, that is non-sense. You example is concerns nuclear physics, not a chemical reaction. It's like counting whales among the number of fish in the ocean. Just because both swim... Plasmic Physics (talk) 12:21, 13 August 2014 (UTC)
No, it is actually pretty funny. Please turn on your humor detector ;-) Boghog (talk) 13:59, 13 August 2014 (UTC)
What am I missing, because I don't get it? Plasmic Physics (talk) 14:21, 13 August 2014 (UTC)
Unless I am terribly mistaken, the above is a subtle example of surreal humour. Boghog (talk) 14:44, 13 August 2014 (UTC)
That explains it - having Asperger's syndrome means that I'm naturally immune to surreal humour. Plasmic Physics (talk) 22:48, 13 August 2014 (UTC)
Would Plasmic agree to discuss proposed edits on Talk pages? If consensus is achieved, the changes could be implemented by another editor. End of problem. Otherwise we get caught up in these litigious and time-consuming discussions. Plasmic's contributions to chemistry are often of highly debatable quality (see discussion above), being supported by his own interpretations (synthesis) or flimsy referencing. Through vetting on a talk page and then seeking consensus, Plasmic could still contribute and the real mission here = serving readers - could move forward. --Smokefoot (talk) 13:50, 13 August 2014 (UTC)
I agreed to discussion of controversial edits; amending my own contributions is hardly controversial. And, all these "litigious and time-consuming discussions" are in actuality the result of consensus building. Plasmic Physics (talk) 14:17, 13 August 2014 (UTC)
  • I would argue we already have a consensus. You've broached the concept of the amphotericity of radicals before in Methylidenecarbene [[17]] and Methylene [[18]]. I seem to remember that in both cases the concept was discussed here and that the consensus was that it was inappropriate (so Smokefoot is right to desire a discussion on talk pages, it would make such records easier to find). Amphoteric is a poor description, radicals don't have special reactivity with both acids and bases, they have wild and all-inclusive reactivity towards almost everything, including each other. That's the sort of chemistry we should be describing. Project Osprey (talk) 14:40, 13 August 2014 (UTC)
I'm not certain about what you're saying. Are you making the sweeping statement that for all radicals, that their radical chemistry is solely notable in such a way that all other chemistry should be ignored? What then of the superoxide ion, and many others? Should we proceed to remove any content for them which does not pertain to their radicality? Plasmic Physics (talk) 22:44, 13 August 2014 (UTC)
We did start to discuss the issue on the talk page. But few others participate there, and more people join in here on the project page. I brought in the example of argon to say we would not call it a base, but Plasmic then brought up helium. Any way that is a side issue to whether Brønsted–Lowry acid–base theory can be used to draw a previously unpublished conclusion to include in an article. The idea here is to be constructive rather than litigious. Since there are more around here that actually know Chemistry. Graeme Bartlett (talk) 12:09, 14 August 2014 (UTC)
Indeed. As I see it, it is a fair conclusion, comparable to the statement "The Oxford Scientific Dictionary will fall to the ground with an acceleration of 9.8 m s-2 , if it is dropped from a height", derived from Newton's theory of gravity. Now, I can almost guarantee, that statement will not be published anywhere. Plasmic Physics (talk) 21:42, 14 August 2014 (UTC)
However we do not include this fact on the Oxford Scientific Dictionary article on Wikipedia. WP:OR allows some application of simple logic, such as counting, adding, converting units, reading a map, but it does not include chemistry related derivations. I would say even working out equilibrium ratios at different temperatures would be WP:OR. Graeme Bartlett (talk) 22:27, 14 August 2014 (UTC)
Yes, but WP:SCICITE overrides WP:OR. Plasmic Physics (talk) 23:04, 14 August 2014 (UTC)
Wrong. First of all WP:OR is a policy while WP:SCICITE is a guideline. Second, WP:SCICITE does not contradict WP:OR. All WP:SCICITE says is that is not necessary to document each and every uncontroversial statement as long as a general source is included that can be used to support these statements. Further WP:SCICITE states that material whose verifiability has been challenged, should always be accompanied by an inline citation. The verifiability of your assertion that Methylidyne radical can be classified as a base has been challenged. If you want to include a statement to that effect, you now must provide a reliable source to support that statement. Boghog (talk) 05:51, 15 August 2014 (UTC)
It should be all too easy to provide an inline citation to BL theory. Plasmic Physics (talk) 06:42, 15 August 2014 (UTC)
You completely missed the point. You assertion has been challenged. If you want the statement to be included in the article, you must provide a reliable source that directly supports your statement. Full stop. Boghog (talk) 06:55, 15 August 2014 (UTC)
Obviously we have a contrasting interpretation of WP:SCICITE. Lets just agree to disagree, shall we? Plasmic Physics (talk) 09:53, 15 August 2014 (UTC)
When it comes to Wikipedia policy, I will not agree to disagree. WP:OR is policy and must be followed. Your interpretation of the WP:SCICITE guideline is WP:WIKILAWYERING and is seriously flawed. Furthermore your actions directly contravene proposed solution that you agreed to above. If other editors question your contribution, the contribution by definition become controversial and you then are obligated to proved reliable sources to support your contribution. So far you have provided no source that directly supports that Methylidyne radical can act as a proton acceptor. Unless you can supply such a source, your edits will be reverted. Boghog (talk) 10:30, 15 August 2014 (UTC)
In order for Methylidyne radical to act as a proton accepting base, the product CH2+ should be stable. The following source suggests CH2+ is not stable:
  • Wetzel TL, Welton RF, Thomas EW, Borkman RF, Moran TF (1993). "The elusive CH2+ ion". Journal of Physics B: Atomic, Molecular and Optical Physics 26 (1). doi:10.1088/0953-4075/26/1/005. "Experiments with an electron cyclotron resonance ion source have been employed in a hunt for the elusive CH2+ ion. The authors' experiments do not find evidence for the existence of stable CH2+ ions. Different levels of ab initio molecular orbital theory have been employed to obtain potential energy curves for CH2+. Although SCF calculations show a small minimum in the potential, post-Hartree-Fock computations indicate CH2+ states to be repulsive." 
Hence it is very doubtful that methylidyne radical could act as a base. Boghog (talk) 06:29, 15 August 2014 (UTC)
Where did you hear that the conjugate acid needs to be stable? There are plenty of known bases, in which the CA is unstable. Post protonation reactions have no effect on the qualitative basicity of the original reacting species. The tetrahydridoborate anion is a well known superbase, the protonated conjugate acid is highly unstable, ejecting a dihydrogen molecule. This neutralization reaction is key to explaining the hydrolysis of tetrahydridoborate salts. Plasmic Physics (talk) 06:42, 15 August 2014 (UTC)
Agreed that the conjugate acid can be unstable, but it should at least be a local minimum along the potential energy surface so that has a finite life time. The above source suggests that the CH2+ configuration is repulsive (i.e., not a local minimum). Boghog (talk) 07:02, 15 August 2014 (UTC)
Here is a more recent reference that shows that it is a minimum: Wang, Haiming; Neese, Christopher Neese; Morong, Christopher P.; Kleshcheva, Maria; Oka, Takeshi (3 October 2013). "High-Resolution Near-Infrared Spectroscopy of CH+
2
and Its Deuterated Isotopologues". The Journal of Physical Chemistry A (ACS Publications) 117 (39): 9908–9918. doi:10.1021/jp3128803.
 .
Within the article there is also says that a group identified it from a spectrum in 1991 which predates your source. Plasmic Physics (talk) 09:53, 15 August 2014 (UTC)
The conflicting literature above supports that the existence of CH+
2
is controversial. Furthermore the references that you have provided above only indicate that it is theoretically possible that CH+
2
CH could act as a base. A reliable source that directly states that CH+
2
CH can act as a proton acceptor is required. Otherwise your assertion becomes WP:OR and has absolutely no place in Wikipedia. Boghog (talk) 10:41, 15 August 2014 (UTC)
(You mean CH?) I could rewrite it as a juxtaposition of standalone sentences, which are all referenceable in their own right. Leaving the reader to draw a conclusion to the same effect. Maybe something like "Methylidyne has Lewis base character", "A proton has Lewis acid character", "CH+
2
is known to exist", "A proton is both a Lewis acid and a Brønsted acid", etc.
Almost nothing would be achieved by reversion, you would removed a other information which is explicitly sourceable, and you'd still be left with a section which contains information on its Arrhenius acidity, which I amended. If you want to make a successful alteration, I would suggest careful dissection of the offending content rather than cauterising it. However, it's best to leave that decision until we've finished the preceding discussion on whether it can simply be rewritten. Plasmic Physics (talk) 11:58, 15 August 2014 (UTC)
By reverting your contribution, we would be eliminating content which is neither verifiable nor notable and bring the article into conformity with long standing Wikipedia policies. Wang et al., 2013 does support the existence of the methylene cation CH+
2
. However we still need a reliable source to support that methylidyne radical (CH) will react with protons to form methylene cation (CH+
2
). Boghog (talk)
Just to clarify: the Wetzel paper[19] concerns the doubly charged CH2+
not CH+
2
. The latter is stable.[20] --Kkmurray (talk) 21:27, 15 August 2014 (UTC)
My mistake. Thanks Kkmurray or clearing that up. Boghog (talk) 21:36, 15 August 2014 (UTC)
@Plasmic Physics: Because your contributions to the Methylidyne radical article are controversial and you have not provided reliable sources to support your contributions, I have reverted them. Per the proposed solution that you agreed to above, you must provide a reliable source that directly supports your assertion before re-adding this material. Boghog (talk) 21:32, 15 August 2014 (UTC)

Nomination for deletion of Template:Material properties (thermodynamics)[edit]

Ambox warning blue.svgTemplate:Material properties (thermodynamics) has been nominated for deletion. You are invited to comment on the discussion at the template's entry on the Templates for discussion page. DH85868993 (talk) 11:13, 14 August 2014 (UTC)

Compeed (hydrocolloid technology)[edit]

Please check if the chemistry behind Compeed plaster is properly described in Techology part. I was using cited sources (patents, Compeed description at Expainthatstuff article]) as well as Amazon ingredients data. -- TigerInWoods (talk) 13:15, 17 August 2014 (UTC)

smart rubber needs a rewrite[edit]

Cross-posting from WikiProject Polymers to get a wider audience: Section title:"Smart rubber page is hard to read". Most of the content of the article appears to have been copied from a single article, on a single type of polymer. Wasn't general at all, and virtually no context. Also no inline citations, so hard to see where most material was being sourced from. I took a stab at a major rewrite myself, but it could probably use some more work. (+)H3N-Protein\Chemist-CO2(-) 22:47, 21 August 2014 (UTC)

template should contain sections on toxicology and environment[edit]

Hi, IMHO a general problem with chemistry articles is, that they have no toxicology section and no environmental fate section in their template. I suggest to build that in. I have found, that most chemists appear uncomfortable with the material, be it because it reaches into other disciplines like biology, environmental sciences etc, or because of a COI if working for a producer, even though each C&En News is full of reports in that area...

I think this is a very important service, that the public looks for, and it ought to be tackled upstream, rather than in a non systematic remediative fashion, pasting a few lines here and there in grandfathered articles.

Can this please be changed? --Wuerzele (talk) 18:24, 27 August 2014 (UTC)

The chembox contains a Hazard section, but it is often incomplete. The GHS labelling misses in most cases (as opposite to de.wikipedia). --Leyo 19:00, 27 August 2014 (UTC)hanks .
Leyo thanks, so we agree. would you help with my request? please steer me to the hunchos working on chem templates.--Wuerzele (talk) 06:36, 31 August 2014 (UTC)
Those hunchos are watching this. There is a bit of an issue there with respect to safety (though I agree that we can display more there) - Wikipedia should be careful with giving 'medical' advice (on the other hand, I once read that Wikipedia is really plainly used as a primary entry point for medical advice due to ease of access and the 'relative reliability' in emergency cases).
You could easily copy the contents of Template:Chembox Hazards into a Template:Chembox Hazards/sandbox and adapt (add) fields, and similarly start creating a Template:Chembox Environment (with an own Template:Chembox Environment/sandbox). The nice thing of those sub templates is that they could be used immediately, and you can show on one or two pages the sandbox 'life' (just use 'section#={{Chembox Environment/sandbox|<fields>}}' instead of 'section#={{Chembox Environment|<fields>}}' and hit preview). --Dirk Beetstra T C 07:37, 31 August 2014 (UTC)
I don't think that adding fields to the chembox template is needed. It's the articles that need their hazard section being completed. For instance, not even the article ethanol contains the official GHS labelling information. In addition, the DSD classification is incomplete, since the chemical hazard symbol is missing (ref).
What about making the GHS parameters compulsory? In cases, where neither an official GHS labelling, nor one by a chemical company is available, this fact (as opposed to cases where it exists, but is missing in the article) would need to be stated explicitly in the chembox. --Leyo 21:42, 31 August 2014 (UTC)
Dirk Beetstra, thanks for your suggestion. I am not interested in the chembox whatsoever, since it does not fit the need- too small. I think I am being misunderstood. I am asking for mandatory description of known ecosystem hazards, and that includes human health. BTW: That has NOTHING to do with medical advice, so shouldnt be any problem; all of you hunchos hearing this?
Leyo thanks for the suggestion-if you mean by GHS labelling info in articles, establishing 15 sections similar to the Global Harmonised System in the body of the article, we are talking the same thing. Although 15 sections sounds too much and section 4-6 (firefighting, acc release info, storage) may be a bit too much for an encyclopedia... I do agree with you, that many many (the majority ?) of WP chemicals contain no hazard/ecosystem/toxicology info. I also agree with you about unambiguously stating explicitly "no info available as of..."! as one does with N.A. in empty cells.--Wuerzele (talk) 05:07, 3 September 2014 (UTC)
Then I am confused, you mention a template in the header of this section, which template do you mean? Also, medical advice is a bit of an extreme case, but the same goes for 'don't stuff this into your tank with piranha's' or 'don't dump this stuff in the nearest canal' .. IMHO, we should be more descriptive, 'this stuff is interfering with the whatever-biological-pathway in fish', 'this stuff accumulates in the larger predator fish which recycles it back into the human food chain in high concentrations' (I think the latter is the main reason why some compounds have that hazard-symbol). I also have problems with the 'mandatory' nature .. but there is nothing against having more information on this, indeed. Do you have an example page which has this info already? --Dirk Beetstra T C 06:06, 3 September 2014 (UTC)
With regard to health matters, it may be worth reaching out to WikiProject Medicine; and borrowing from their well-developed policies on the inclusion and referencing of such material. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 08:34, 26 September 2014 (UTC)

@Wuerzele: I was not referring to a MSDS, but to labelling (example for dichlorophen; the de.wikipedia article contains this information in the chembox). --Leyo 10:17, 20 September 2014 (UTC)

Sulfonyl and Sulfone[edit]

As completely changing the definition a functional group might prove contentious, I thought I’d better bring this up here first.

Sulfone.png

Currently we describe the functional groups Sulfonyl and Sulfone as being the same thing i.e. R-S(=O)2-R'. Both pages use the same image displayed on the right. The IUPAC goldbook has no definition for sulfonyl but does list RS(=O)2R for sulfones and RS(=O)2OH for sulfonic acids. I think sulfonyl should probably refer to sulfonyl halides RS(=O)2X and that it should be merged into that page. I’d be interested in hearing any other opinions though. Project Osprey (talk) 13:05, 29 August 2014 (UTC)

The former refers to the functional group, the latter refers to the parent compound, in the same way as "carboxyl" and "carboxylic acid" relate. Plasmic Physics (talk) 03:14, 30 August 2014 (UTC)
If that's true then the page still need to be changed; to define sulfonyl as being RS(=O)2Y, where Y = C, OH, X etc. Project Osprey (talk) 12:53, 30 August 2014 (UTC)

The sulfonyl can also be considered a fragment in inorganic compounds, where it is more commonly termed 'sulfuryl', such as in sulfuryl chloride and sulfuryl fluoride. I quite like the fact Wikipedia has separate articles for related but distinct fragments, functional groups and classes of molecules such as these. It makes it easier for a reader to search for the word when they encounter it, and find an article that quickly and unambiguously defines the word, provides a structure and links to specific examples or related articles. I actually think merging such articles does a serious disservice to our readers. If I don't know what 'sulfonyl' means and I get redirected to sulfone, I will have to read a load of irrelevant information about sulfones before getting the definition I actually want. I feel we should change our policy on this and fix all such situations throughout chemistry articles on Wikipedia. --Ben (talk) 17:18, 30 August 2014 (UTC)

I'm fine with having pages on fragments, I just don't think this one is described properly. We already have a page on Sulfuryl. Project Osprey (talk) 19:39, 30 August 2014 (UTC)

Acid-base indicators: a graphic view[edit]

I have created a graphic view of the pH indicators giving their operation range and the associated colour change. The image can be found here: https://commons.wikimedia.org/wiki/File:A_graphic_view_of_Acid-Base_Indicators.svg

I would like to know where the image can be placed for a better usage. (Damitr (talk) 7:59 am, Today (UTC−4))

It's an impressive graphic! pH indicator would be one good place to use it. By the way, the way I see it rendered on my Windows/Chrome system, three of the indicator names are displaced to, or beyond, the left edge of the image. As it's SVG, this could easily be corrected. Maproom (talk) 12:29, 2 September 2014 (UTC)
It looks good. Though thymol blue is missing the base side of its colour change. For Crystal violet I cannot see green or violet in the colour band. There are several indicaters here with no article, for example Methyl green. Graeme Bartlett (talk) 21:22, 18 September 2014 (UTC)

Wikipedia talk:Articles for creation/Boronizing and Boriding[edit]

Dear chemistry experts: Apparently these two pages are about the same topic. Is any of the information/sourcing in the draft suitable to expand the stub? —Anne Delong (talk) 02:27, 18 September 2014 (UTC)

Smokefoot has taken care of this with a merge. Graeme Bartlett (talk) 21:23, 18 September 2014 (UTC)
Sorry if I acted too swiftly, but the merge seemed pretty obvious. I am still refining the article, parent boriding, but others are welcome to join in. It seems to be an important topic, so we can all thank Anne for rescuing another topic. --Smokefoot (talk) 22:27, 18 September 2014 (UTC)
I have moved the draft to mainspace and added the appropriate "merge to" and "merge from" templates to preserve attribution. One more off my list... —Anne Delong (talk) 12:09, 20 September 2014 (UTC)

Water ionizer[edit]

Water ionizer appears to be a page on some form of quackery. It's not a new page but its recently had a huge surge in page views, currently ~15,000 per day, making it the most viewed chemistry page so far this month. I'm going to try and clean it up but the science is shaky and WP:MEDRS will likely raise its head, so if anyone is free I'd appreciate a hand. Project Osprey (talk) 22:11, 18 September 2014 (UTC)

Looks like fringe science that would not be cured even by Earthing Therapy, although boriding certain editors might be worth considering. More seriously, you could point out that the autoionization constant for water is a constant, see Self-ionization of water.--Smokefoot (talk) 22:27, 18 September 2014 (UTC)
Oh its plenty wacky, for example autoionization wouldn't apply as this device only produces negative ions. I'm guessing that the 'science' might actually be electrolysis to produce small amounts of hydrogen peroxide which then breaks down to form all sorts, with a net increase in pH. That would make it a hybrid between hydrogen peroxide therapy and electrolysed water. A perfect irony is that its marketed as an anti-oxidant. It has the usual crazy claims, my favourite being that it can protect you from nuclear fallout.

npp for category tool[edit]

Please comment. Gryllida (talk) 23:38, 23 September 2014 (UTC)

Royal Society of Chemistry - Wikimedian in Residence[edit]

Hi folks,

I've just started work as Wikimedian in Residence at the Royal Society of Chemistry. Over the coming year, I'll be working with RSC staff and members, to help them to improve the coverage of chemistry-related topics in Wikipedia and sister projects.

You can keep track of progress at Wikipedia:GLAM/Royal Society of Chemistry, and use the talk page if you have any questions or suggestions.

How can I and the RSC support your work to improve Wikipedia? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 15:26, 24 September 2014 (UTC)

I was under the impression the Wikimedian was going to have a chemistry background? V8rik (talk) 17:31, 24 September 2014 (UTC)
Sorry to disappoint; I'm a Wikimedian in residence at a chemistry organisation, not a chemist in residence at a Wikimedia organisation. There are plenty of very knowledgeable chemists there, upon whose expertise I can call as needed. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 17:51, 24 September 2014 (UTC)
How can you and the RSC support our work? Good question. We would like to see more active and knowledgeable editors, that is for sure. V8rik (talk) 19:44, 25 September 2014 (UTC)
This appointment seems ridiculous - and possibly arrogant - to have a nonchemist installed in this position at the RSC. I guess we can look forward to the RSC pushing their "branding".--Smokefoot (talk) 22:31, 25 September 2014 (UTC)
Does anyone have any use for the Wikipedian in Residence at the RSC? I mean this legitimately, because I have no idea what this position is about. Is this just a person at RSC who helps the chemists there edit wikipedia articles? Is he just going to be running training sessions or something, or is he supposed to be like helping us edit Chemistry articles himself? If the latter, I feel like his time will be more or less wasted in our very technical field, for which a single year is probably inadequate preparation. If the former, I guess I don't care all that much if he's a chemist or not. Then again, I'm not paying his salary, so it's none of my business who the RSC hires and for what purpose, just as long as he's not going to start spamming us or otherwise disruptively interfering with us. 0x0077BE [talk/contrib] 01:04, 26 September 2014 (UTC)
I'll see if I can get the job description re-published (it was online during the recruitment phrase, but disappeared, as is usual, when the deadline passed). But in brief, the role is about outreach, training and awareness raising, not simply editing; see Wikimedian in Residence and outreach:Wikipedian in Residence for background.. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 08:02, 26 September 2014 (UTC)
I've no interest in "pushing branding", nor have I been asked to do so. I've been a Wikipedian in Residence several times before, and that's never been an issue. Please judge me by my actions. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 08:02, 26 September 2014 (UTC)
Thank you - that's a primary objective of the initiative. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 08:02, 26 September 2014 (UTC)
Welcome, Andy! Encouraging chemists at the RSC to get involved writing and improving chemistry articles would be of the most direct help to the project. I suspect one COI challenge you will face is RSC staff who want to work on RSC-related articles. Good luck in your new position. --Mark viking (talk) 03:28, 26 September 2014 (UTC)
Thank you. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 08:02, 26 September 2014 (UTC)
There is already some kind of collaboration with ChemSpider. We use ChemSpider and ChemSpider uses Wikipedia, but is this process documented anywhere, and is there any effort to get the connection up to 100% accurate? Perhaps we need a page called WP:ChemSpider where this process is described. Is there a program to provide access to RSC journals to Wikimedians prior to free access from next year? Graeme Bartlett (talk) 05:57, 26 September 2014 (UTC)
WP:ChemSpider is a good idea; thanks. I'll raise it with the ChemSpider team next week. I'm already in discussion regarding journal access; no promises, but watch this space! Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 08:02, 26 September 2014 (UTC)
I think you’re going to face quite a bit of this in your early days. The problem is that you’ve just been appointed here out of the blue. It is commendable for the RSC to want to get involved, but they might have thought to have talked to us about it. However, in the spirit of good faith, welcome! What you can do for us is probably tied-in with your role and like the others I would like to see some detail on what that is. More editors though, would always be welcome. This being an outreach role, what are you hoping we can do for you? Project Osprey (talk) 09:14, 26 September 2014 (UTC)
Thank you. Like I said, I've done this before ;-) Obviously, I wasn't involved in specifying and conducting the recruitment process, but I do know that the RSC spent considerable time talking to Wikimedia UK, and to members of the editing community in the UK, including hosting an editathon (at which I volunteered as a trainer) and attending Wikimania and other events. Please see the links above for more on the WiR role. I'm already getting lots of useful ideas, such as the WP:ChemSpider suggestion above and a request on my talk page for help sourcing images. Another way members of this project can help is, as I introduce more chemists to the community of editors, to welcome, and even mentor, them. Those of you in the UK (or elsewhere - I may be travelling) might also volunteer at training or outreach events. I'll return with other ideas for collaboration as the role develops. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 09:42, 26 September 2014 (UTC)
Andy: Do you have access to all of the journals the RSC publish? Currently there are two articles I would like to see if the content is worth while. One for example I have listed as "C. C. Addison C. D. Garner W. B. Simpson D Sutton, S. C. Wallwork Proceedings Chemical Society 367 1964" but the online index does not even seem to mention "article" names. So perhaps it is available on paper. Graeme Bartlett (talk) 08:11, 29 September 2014 (UTC)

Media[edit]

What about asking RSC for releasing some of their pictures or video clips on e.g. chemical reactions, lab equipment, etc. under a free license? Or advertising this request among interested RSC members? See also Wikipedia:WikiProject Chemistry/Image Request or Category:Wikipedia requested photographs of chemical compounds. --Leyo 12:03, 27 September 2014 (UTC)

"carbon fiber"[edit]

The usage of Carbon fiber (edit | talk | history | protect | delete | links | watch | logs | views) is under discussion, see talk:carbon (fiber) -- 65.94.171.225 (talk) 04:23, 25 September 2014 (UTC)