Commons:WikiProject Chemistry/Deletion requests

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File:(2S,3S)-3,4-dimethyl-2-phenylmorpholine.jpg[edit]

{{badJPG}}; orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:14, 22 January 2017 (UTC)

File:2-ethyl-6-(3-methoxy-phenyl)-4-propyl-morpholin-3-one.jpg[edit]

{{badJPG}}; orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:13, 22 January 2017 (UTC)

File:(5S)-2-(3-methoxyphenyl)-5-methyl-4-propylmorpholin-2-ol.jpg[edit]

{{badJPG}}; orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:12, 22 January 2017 (UTC)

File:2-hydroxy-5-(4-propylmorpholin-2-yl)benzamide.jpg[edit]

{{badJPG}}; orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:12, 22 January 2017 (UTC)

File:4-(4-propylmorpholin-2-yl)phenol.jpg[edit]

{{badJPG}}; orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:11, 22 January 2017 (UTC)

File:Nociceptive morpholine dopamine agonist.jpg[edit]

{{badJPG}}; orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:11, 22 January 2017 (UTC)

File:3-benzylmorpholine.jpg[edit]

{{badJPG}}; orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:10, 22 January 2017 (UTC)

File:3-methyl-4-nitroso-2-phenyl-morpholine.jpg[edit]

Orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:09, 22 January 2017 (UTC)

File:4-Isopropyl-2-phenylmorpholine.jpg[edit]

Orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:08, 22 January 2017 (UTC)

File:2-phenyl-3,5-dimethylmorpholine.jpg[edit]

Orphaned/replaced in en:Substituted phenylmorpholine. Leyo 20:08, 22 January 2017 (UTC)

Categories for discussion[edit]

Category:Thioic acids[edit]

No obvious difference to Category:Thioacids (both have some comparable diagrams of the functional groups). Propose merge, and then subcats for Category:Thiocarbonates vs thiocarboxylic variants. DMacks (talk) 19:37, 19 September 2016 (UTC)

Sounds reasonable. For the record, the original rationale for having separate categories was:
  • a thioacid is a sulfur analogue of an oxoacid
  • a thioic acid is a sulfur analogue of a carboxylic acid (what you call a thiocarboxylic acid)
By 'analogue', I mean replacement of one or more of the oxygen atoms by sulfur atoms.
If you consider carboxylic acids to be oxoacids, then "thioic acids" (or "thiocarboxylic acids") would be a subcategory of "thioacids".
Happy to help with the changes. --Ben (talk) 11:26, 20 September 2016 (UTC)
@DMacks: Would you like to respond? --Leyo 14:28, 3 January 2017 (UTC)

Category:Alpha and beta proteins (a+b)[edit]

movement is not necessary: thousands of files linking to this category Wieralee (talk) 13:38, 16 April 2016 (UTC)

What exactly are you talking about? What is your suggestion? --Leyo 20:44, 16 April 2016 (UTC)
Leyo is right about the bots, and so on, but it was actually wrong from me to rename this category. I thought it was a bad name in contradiction of our conventions, as was the previous name of the mother-category ("Structural Classification of Proteins (SCOP)"), but if we mimic the categories organization of SCOP, we need the parentheses as there is one "homonym", "Alpha and beta proteins (a/b)" (named "Alpha and beta proteins (a or b)‎" here, since "/" can't be in titles). I'm moving back the category to its old name (but I'm still somewhat circumspect with these categories). Rhadamante (talk) 21:57, 17 April 2016 (UTC)
of course, I wrote that before seeing that all sub-cats had already been bot-moved. Gasp. Rhadamante (talk) 21:59, 17 April 2016 (UTC)

Category:Silylamines[edit]

Redundant to Category:Silicon-nitrogen compounds...proposing merge. Seems like just different terminology for same subject. All entries here seem analogous to ones there (or subcats of there). DMacks (talk) 19:59, 13 April 2016 (UTC)

I don't have strong feelings either way on this one, but silylamines could be a subcategory of silicon-nitrogen compounds. Compounds that would belong in Si-N but not silylamines would be things like N-silyl imines, silicon isocyanates and silicon nitride. Silylamines would be silicon sp3 silicon bound to sp3 nitrogen. Although some of these categories seem pretty academic, I believe they get more useful over time as the number of images on Commons massively increases. --Ben (talk) 21:28, 13 April 2016 (UTC)
My concern will be the exact opposite : silylamines = silanes with amine function(s). "Silicon-nitrogen compounds", as per all other categories named the same way, doesn't make any sense to me. Chemically even less. I mean are they compounds only consisting of nitrogen and silicon ? In this case, the term is not synonym with silylamines, because there is no hydrogen. Are they compounds that have both silicon and nitrogen, along with any other kind of atoms ? In that case I don't see how the term would be equivalent to "silylamines". Rhadamante (talk) 21:55, 13 April 2016 (UTC)
When I created all the "element X-element Y compounds" categories, I did so with X-Y bonds in mind. The reason was, I often want to find all compounds that contain an X-Y bond, whether organic or inorganic. There are plenty of useful comparisons that can be made, such as between P-S bonding in SPCl3 and SPPh3. It serves as a really useful indexing and searching tool in the absence of structure-based searching.
To me, a category like silylamines is useful for finding compounds containing Si-N< fragments. If it includes molecules where the silicon and nitrogen atoms are widely separated then it's less interesting and useful, since the two functionalities are unlikely to influence each other (unless there's some non-covalent interaction between them).
There's no real limit on categories. We can have as many different categorisations as we want, as long as they're useful. I aim to have a separate category for each distinct substance (compound, allotrope, ion, chemical species, whatever as long as it's distinct and well-defined). The aim is to make it easy to find images that depict the same substance, even though their filenames might be in different languages and otherwise quite difficult to quickly locate simultaneously using the search box. It also makes recategorisation much quicker and easier as new, more specific parent categories become available.
Ben (talk) 23:49, 13 April 2016 (UTC)
I can understand the usefulness of subcats for classifying different N hybridizations, and I assumed that the meaning of "X–Y compounds" was direct bonding. However, we have very few that aren't amines, so I wonder if a more useful scheme is to have subcats for those (silylimines, iminosilanes, N-silylamides, etc), if we start to overpopulate the parent Si–N cat, rather than having to know the intermediate step (for example, at HMDS is a silylamine is a Si–N) for the more common cases. That is, keep an on-average flatter tree to simplify tree navigation. Some day there might be value to having a deep tree from Si–N via the nature of the Si and/or N and/or their bond to each individual chemical's own cat as a highly specific intersection. But for now, I dislike violating the COM:CAT "simplicity principle" with such sparse subsubcats. On en.wp, for example, the most common pattern for newbie editors is to draw all their structures from scratch, which means they don't know how to easily find them and we then have to figure out where best to categorize them. I think having too narrowly focused and too deeply nested cats makes both those tasks harder. DMacks (talk) 02:56, 14 April 2016 (UTC)
Good points. I generally aim for moderately full categories, for the reasons you give. You have to use your judgement to strike a balance between a simple tree and having categories that are empty enough that you can browse the images in them quickly. At present, the problem of overfull categories seems to affect organic compounds much more than inorganic ones. See Category:Tertiary amines, for example.
Perhaps the current situation with silylamines and Si-N compounds has arisen because Rhadamante and I have different ideas about how categorisation should be on Commons. I'm happy to discuss general views here or elsewhere.
For really easy navigation, I have some periodic table-based tools at User:Benjah-bmm27/compounds by element, such as User:Benjah-bmm27/compounds by element/nitrogen#Element-nitrogen compounds for E-N compounds. We could definitely think about using things like these to help users find the right category for their image.
I tried to make tables (here) for finding organics, but they're a bit wordy. I find tables with structural images, such as this one, more useful for organics, as long as the category describes a structure that can easily be drawn.
--Ben (talk) 08:08, 14 April 2016 (UTC)

@DMacks, Benjah-bmm27: Do I understand correctly that you both reached consensus on this? It's all over my head, but it would be great if we could close discussion. - Themightyquill (talk) 08:31, 2 June 2016 (UTC)

Kept as in-use[edit]

This deletion debate is now closed. Please do not make any edits to this archive. You can read the deletion policy or ask a question at the Village pump. If the circumstances surrounding this file have changed in a notable manner, you may re-nominate this file or ask for it to be undeleted.

File:3DAmmonium mandelate.png[edit]

Incorrect structure/geometry at ammonium. Leyo 00:13, 17 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:09, 19 December 2015 (UTC)
  • Ball-and-stick models absolutely need to have an accurate geometry. Otherwise, they are misleading. Hence, still Symbol delete vote.svg Delete. --Leyo 16:53, 22 December 2015 (UTC)

Kept: . .     Jim . . . . (Jameslwoodward) (talk to me) 23:39, 28 December 2015 (UTC)

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File:3D Ammonium tartrate.png[edit]

Incorrect structure: hydrogens in ammonium are not bound like that. Leyo 00:12, 17 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:10, 19 December 2015 (UTC)
  • Delete. It is misleading to show naked ammonium centers, especially such slick graphics which implies advanced knowledge (but results from the opposite). --Smokefoot (talk) 13:33, 19 December 2015 (UTC)

Kept: . .     Jim . . . . (Jameslwoodward) (talk to me) 23:39, 28 December 2015 (UTC)

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File:3D Sodium carbamate.png[edit]

Incorrect structure: sodium is not covalently bound. Poor quality anyway. Leyo 00:03, 17 December 2015 (UTC)


Kept: In use .     Jim . . . . (Jameslwoodward) (talk to me) 23:37, 28 December 2015 (UTC)

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File:3d Sodium cacodylate.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 00:02, 17 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:39, 19 December 2015 (UTC)
  • Ball-and-stick models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 17:06, 22 December 2015 (UTC)

Kept: This, and the remaining similar files below, are all in use. .     Jim . . . . (Jameslwoodward) (talk to me) 23:38, 28 December 2015 (UTC)

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File:3D Sodium caprylate.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 00:02, 17 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:37, 19 December 2015 (UTC)
  • Ball-and-stick models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 17:06, 22 December 2015 (UTC)

Kept: In use .     Jim . . . . (Jameslwoodward) (talk to me) 23:36, 28 December 2015 (UTC)

This deletion debate is now closed. Please do not make any edits to this archive. You can read the deletion policy or ask a question at the Village pump. If the circumstances surrounding this file have changed in a notable manner, you may re-nominate this file or ask for it to be undeleted.

File:3D Sodium caproate.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 00:01, 17 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:37, 19 December 2015 (UTC)
  • Ball-and-stick models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 17:08, 22 December 2015 (UTC)

Kept: in use .     Jim . . . . (Jameslwoodward) (talk to me) 23:36, 28 December 2015 (UTC)

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File:3D Sodium lactate.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 00:01, 17 December 2015 (UTC)

  • File improved. It's not a matter of deleting, but of improving. Thanks for helping. Claudio Pistilli (talk) 06:41, 18 December 2015 (UTC)
  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:40, 19 December 2015 (UTC)
  • Ball-and-stick models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 17:08, 22 December 2015 (UTC)

Kept: In use .     Jim . . . . (Jameslwoodward) (talk to me) 23:35, 28 December 2015 (UTC)

This deletion debate is now closed. Please do not make any edits to this archive. You can read the deletion policy or ask a question at the Village pump. If the circumstances surrounding this file have changed in a notable manner, you may re-nominate this file or ask for it to be undeleted.

File:3D Sodium caprate.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 00:01, 17 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:41, 19 December 2015 (UTC)
  • Ball-and-stick models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 17:09, 22 December 2015 (UTC)

Kept: In use .     Jim . . . . (Jameslwoodward) (talk to me) 23:34, 28 December 2015 (UTC)

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File:Sodium orto-periodate 3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:55, 16 December 2015 (UTC)

  • File substituted. The structure was corrected, thank you for helping. Claudio Pistilli (talk) 18:33, 17 December 2015 (UTC)

Kept: In use] Natuur12 (talk) 15:41, 28 December 2015 (UTC)

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File:3D Sodium methyl paraben.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:53, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:42, 28 December 2015 (UTC)

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File:Sodium benzenesulfonate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:50, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:43, 28 December 2015 (UTC)

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File:Disodium phenylphosphate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:49, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:43, 28 December 2015 (UTC)

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File:Sodium phenyl-butyrate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:47, 16 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:50, 19 December 2015 (UTC)
    Ball-and-stick and calotte models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 22:21, 22 December 2015 (UTC)

Kept: In use Natuur12 (talk) 15:44, 28 December 2015 (UTC)

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File:3D Sodium phenyl-acetate.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:47, 16 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:48, 19 December 2015 (UTC)
    Ball-and-stick and calotte models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 22:22, 22 December 2015 (UTC)

Kept: In use Natuur12 (talk) 15:44, 28 December 2015 (UTC)

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File:Sodium pantothenate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:47, 16 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:49, 19 December 2015 (UTC)
    Ball-and-stick and calotte models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 22:23, 22 December 2015 (UTC)

Kept: In use Natuur12 (talk) 15:44, 28 December 2015 (UTC)

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File:Sodium picramate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Poor quality anyway. Leyo 23:46, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:44, 28 December 2015 (UTC)

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File:Sodium picrate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:45, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:44, 28 December 2015 (UTC)

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File:Sodium propanoate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:45, 16 December 2015 (UTC)

  • This looks to have been changed. Though I would like to see the anion drawn more like what you see in File:Ammonium-acetate-3D-balls.png with a dotted line across the two oxygens. Graeme Bartlett (talk) 07:50, 19 December 2015 (UTC)
    Ball-and-stick and calotte models absolutely need to have an accurate geometry and size of atoms. Otherwise, they are misleading like in this case. Hence, still Symbol delete vote.svg Delete. --Leyo 22:24, 22 December 2015 (UTC)

Kept: In use Natuur12 (talk) 15:44, 28 December 2015 (UTC)

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File:Sodium acrylate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:44, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:45, 28 December 2015 (UTC)

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File:Sodium salicylate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:43, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:45, 28 December 2015 (UTC)

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File:Sodium sorbate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:43, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:45, 28 December 2015 (UTC)

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File:Sodium trichloroacetate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 23:41, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:45, 28 December 2015 (UTC)

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File:Sodium telluride3D.png[edit]

Likely incorrect structure/geometry; poor quality (assembled). Leyo 23:39, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:46, 28 December 2015 (UTC)

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File:Sodium tellurite3D.png[edit]

Incorrect structure: potassium and sodium are not covalently bound. Leyo 23:37, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:46, 28 December 2015 (UTC)

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File:Sodium orthotellurate3D.png[edit]

Incorrect structure: sodium are not likely covalently bound. Leyo 23:37, 16 December 2015 (UTC)

We must better and not delete because it's missing in Wikipedia. Thank you for helping. Claudio Pistilli (talk) 13:35, 17 December 2015 (UTC)

There is no urgent need for ball-and-stick structures for all possible salt compounds. No image is better than a factually incorrect one. --Leyo 13:43, 17 December 2015 (UTC)

Kept: In use Natuur12 (talk) 15:47, 28 December 2015 (UTC)

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File:Sodium trithionate3D.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 22:51, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:49, 28 December 2015 (UTC)

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File:Sodium potassium tartrate3D.png[edit]

Incorrect structure: potassium and sodium are not covalently bound. Leyo 22:47, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:49, 28 December 2015 (UTC)

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File:Sodium monothiophosphate 2.png[edit]

Incorrect structure: sodium is not covalently bound. Leyo 22:29, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:49, 28 December 2015 (UTC)

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File:Sodium dithiophosphate.png[edit]

Incorrect structure: sodium is not covalently bound. See Category:Sodium dithiophosphate for correct alternatives. Leyo 22:23, 16 December 2015 (UTC)


Kept: In use Natuur12 (talk) 15:49, 28 December 2015 (UTC)


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