User talk:Benjah-bmm27

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Contents 1 Nitrosation 2 Request for edit summary 3 Polyethylene terephthalate 4 Jmol and Chemistry 5 Uranium Trioxide 6 Arsine and co. 7 The new amino acid images 8 UO3 9 Drawing copied from Cotton (1991) 10 Sulfamic acid 11 Uranium trioxide structure 12 Jmol and more ... 13 Nice work - and a tip on how to draw bitetrahedra 14 Monomeric BuLi structure is incorrect 15 License tagging for Image:Malathion.png 16 Graphic Designer Barnstar - Molecular Diagrams 17 BuLi 18 Tetrazene 19 3D Images 20 Thiosulfate 21 ⇌ 22 UO3 structure 23 Thanks 24 Isocyanate pages without images 25 Elaidic Acid 26 chip pan fire photo 27 3D images 28 helicene 29 Molecular models 30 Image tagging for Image:DS-Visualizer-Pro.png 31 Thanks! 32 Thanks 33 Still more thanks 34 ammonia 35 Question 36 Minor edits reminder 37 Caffeine structure image 38 Please consider also warning vandals 39 3D picture of glyceraldehyde 40 Hello. I created a baby stub for the article benzethonium chloride. 41 Wow! 42 Hello Benjah-bmm27, 43 Glyceraldehyde 44 MakingMolecules 45 special:chemicalsources 46 2D Skeletal formulae 47 Hi on selegiline case 48 Sodium acetate image 49 Glucose images 50 Hey :-) 51 Chlorine pentafluoride 52 A favor 53 dihydrolipoic acid 54 hydrogen sulfide 55 Image tagging for Image:Hollyberryine-3D-vdW.png 56 Applied and Pure Chemistry 57 MAO 58 Phenyl 59 Images 60 Chemistry Question 61 Thanks! 62 Fluoxetine 63 Free beer! 64 Molecular accuracy 65 Chloroform 66 Help! 67 SVG 68 Perrhenic acid 69 Hexamethyltungsten structure 70 Sytematic Naming - Chloroacetic acids 71 Bedfordshire project user box

[edit] Nitrosation

Hi, I was just wondering if you could help me with a problem i have. I'm a 3rd year chemist and i'm trying to do a project that involves the mechanism of nitrosation of secondary amines by the nitrosonium cation. Don't suppose you know the mechanism for the reaction do you (arrow pushing organic mechanism, not the kinetic mechanism). Thanks Sameyley 15:01, 11 February 2007 (UTC)

Hi Sam. I assume the reaction you're studying is secondary amine + nitrosonium → nitrosamine + proton.

R₂NH + NO⁺ → R₂NNO + H⁺

I would imagine the mechanism is similar to that for diazotisation, but because the amine is seconary, it cannot tautomerise and go on to form a diazonium compound.

A mechanism for diazotisation is here: http://www.organic-chemistry.org/frames.htm?http://www.organic-chemistry.org/namedreactions/diazotisation.shtm

Here's a 1977 paper on the nitrosation of secondary amines: http://www.springerlink.com/content/u15h802n68622117/

Hopefully you can access that through your university network or with a password from the departmental library.

Any further problems, just leave another message here.

Good luck!

Ben 15:33, 11 February 2007 (UTC)

Thanks, that was very helpful, that was the reaction mechanism that i had assumed, i was just struggling to find anything to back it up. Thanks for your help. Sameyley 17:08, 11 February 2007 (UTC)

[edit] Request for edit summary

Hi. I am a bot, and I am writing to you with a request. I would like to ask you, if possible, to use edit summaries a bit more often when you contribute. The reason an edit summary is important is because it allows your fellow contributors to understand what you changed; you can think of it as the "Subject:" line in an email. For your information, your current edit summary usage is 2% for major edits and 100% for minor edits. (Based on the last 130 major and 1 minor edits in the article namespace.)

This is just a suggestion, and I hope that I did not appear impolite. You do not need to reply to this message, but if you would like to give me feedback, you can do so at the feedback page. Thank you, and happy edits, Mathbot 16:00, 28 February 2006 (UTC)

[edit] Polyethylene terephthalate

Good job on the new image; keep up the good work! TenOfAllTrades(talk) 21:11, 2 March 2006 (UTC)

[edit] Jmol and Chemistry

Thanks for indicating your interest in this project. I also see that you have added your name to the participants in Wikipedia:WikiProject Chemistry. Welcome. As far as the Jmol project is concerned, it may take a bit of time to get moving. I would like to have some of the discussion on this done by e-mail as we will be testing it on a different Wiki. Could you go to my user page and use the appropriate userbox to e-mail me and let me know your e-mail address? I will then reply with mine. --Bduke 22:47, 9 March 2006 (UTC)

[edit] Uranium Trioxide

Thank-you for your timely and welcome edits on this page. I was getting tired being the only one holding back the contention by one other editor that clouds of UO3 gas were being produced from uranium combustion. --DV8 2XL 18:43, 14 March 2006 (UTC)

Oh dont grill me, toast me, boil me or fry me in hot oil ..... Monty Pytons Uranium Trioxide is a hot topic, but if you have a good suggestion DO IT! I also try and get reverted from time to time! Thanks to get everything right! Phd only means that you know more about one tiny little and forgot most of the stuff learned for your master.--Stone 20:39, 14 March 2006 (UTC)

[edit] Arsine and co.

Hi, it looks like you help insert ChemDraw. If so, could you please look at arsine. The drawing does not match the structure (the H-As-H angle is misrepresented vs the text, which is correct).And if you have any free time, here are some molecules awaiting their portraits:

asparagusic acid, Benzo(C)cinnoline, bismuthine, Cupferron - a tricky one as it is the NH4+ salt, nitrosonium (i.e. just the diatomic), and Phenylhydroxylamine, where you can simply edit your PhNO pic. I dont know how to upload ChemDraw, so if you could point me to simple instructions, I can start to do this too. --Smokefoot 00:58, 18 March 2006 (UTC)

Hi Smokefoot. I'll definitely get some images done for those articles. As for uploading images from ChemDraw, I copy the structure I've drawn in ChemDraw to the clipboard. Then I open Photoshop and paste it into a blank document. Then I save the image as a hi-resolution PNG. I think there are other programs available free if you don't have access to a version of Photoshop. Hope this is helpful. I can give you more detailed instructions if you'd like. Cheers. Ben.

I've done them all! Let me know if you like them. Ben.

Ben - nice stuff. BTW, for cacodylic acid, it's tetrahedral (like most 4-coordinate main group things lacking lone pairs), so you could still more accurately represent it by modifying say AsH3, replacing l.p. with =O, 2xH with Me's and one H with OH. I dont know the structural details, but to the extent that anyone looks up cacodylic acid, we dont want them thinking it's planar. I understand if you dont have time for this.--Smokefoot 21:55, 19 March 2006 (UTC)

[edit] The new amino acid images

Hi Ben. I see you have uploaded new "high resolution" images for the amino acids and have replaced the old structural ones with them. First - i didn't like the old images too much either, but you can't wipe out someone's contribution just b/c you don't like their style, an edit is suposed to improve the article - yours don't - in fact they worsen it b/c the images you have removed and the color ones next to them were sets - they both had similar spatial position of the atoms, well not anymore. Another thing is the size of your images - ~ 20K, for the ~3K the old ones have. That's too much for a simple structure such as an amino acid. Now if you want to draw images there is plenty for you to do, just check Category:Chemistry_stubs, Category:Pharmacology_stubs and List of organic compounds. I suggest that you take a sub class of similar structures that noone has worked on it yet, this way all the images in that sub-class will have the same style - see the bile pigments Biliverdin, Bilirubin, Urobilin and Urobilinogen. -- Boris 04:56, 20 March 2006 (UTC)

Hi Boris - sorry you didn't like my updates. You're right - my skeletal structures for amino acids do not coincide with Michael Ströck's 3D ones. However, I think having a skeletal structure is a lot neater and clearer than lots of C-H's. Having ambiguous planar representations of molecules whose 3D structure is very important is not good. The bond angles are realistic and the stereochemistry is apparent in my versions. In fact, the older images I wrote over were the D-enantiomers, the ones not found in nature, and therefore of much less interest.

As for the 20K issue, Wiki automatically resizes images when the page is rendered, meaning that 20K of image is not downloaded - it's probably about the same as before. The pages will not load more slowly. The WikiProject on Chemistry recommends wholeheartedly in uploading hi-res PNG structures, so that's why I've done it. There is no disadvantage in this format.

I'll happily add some structures for currently unillustrated groups of compounds, as you suggest, but I do feel I was right to update the amino acids. I was being bold! Hopefully we can get the amino acid articles to a state that we're both happy with.

Cheers

Ben 15:43, 20 March 2006 (UTC)

You have to work with Michael to find a solution, i like the idea of having two images next to each other, but you have to chose another way to draw these structures becasue with some of the bulky amino acids like Arginine, Tryptophane the currunt sceletal images will make it hard for the color ones to fit.
The images you have replaced were not the D-enantiomers, the ones before them were (for more see Wikipedia:WikiProject_Chemicals/archive0, section "76. Amino acids"). -- Boris 19:50, 20 March 2006 (UTC)

I've been able to make my own 3D structures in the style Michael used. I've added a modified skeletal structure and my own 3D image of arginine. They looked too small side-by-side so I put them one on top of the other. What do you think? Ben 11:11, 21 March 2006 (UTC).

Excellent. Now since you've started it, you have to finish it - don't stop in the middle. -- 14:30, 21 March 2006 (UTC)

I've been working on these all day and I'll keep going till it's done. Hopefully in a few hours time. Ben 14:44, 21 March 2006 (UTC).

All complete. 1 day's work! Have fun with them. Ben 21:48, 21 March 2006 (UTC).

I just wanted to let you know that I think they look great. Thanks for all the hard work. --Ed (Edgar181) 21:58, 21 March 2006 (UTC)

My pleasure! Ben 22:15, 21 March 2006 (UTC)

You are not done yet :). Here's more - Category:Amino acids. I'll star alphabetically with 1-Aminocyclopropane-1-carboxylic acid, skipping the ones you did, to put infoboxes where they are needed or change their look to make them look similar, you make the images the same way. To give me some time you can change the images for Arg and istead of having the side chain go horizontal make it go vertical, this way we can fit the two images next to each other instead on the top of each other. -- Boris 01:01, 22 March 2006 (UTC)

OK, I'll re-draw arginine but I can't promise to do all those other unusual amino acids right away. I'm happy to do them eventually, but there's 50 odd so it may be a while. You're a hard taskmaster! Thanks for the info though. Ben 09:16, 22 March 2006 (UTC)

How about you put the opening <style> tag at Science page? -- Boris 18:17, 22 March 2006 (UTC)

MS Word made that page for me - not my fault! Ben 18:59, 22 March 2006 (UTC)

[edit] UO3

Before you break your hand patting James on the back here are some places you want to visit to get up to speed:

• Wikipedia:Requests for arbitration/Depleted uranium
• Wikipedia:Requests for arbitration/Depleted uranium/Evidence
• Wikipedia:Requests for arbitration/Depleted uranium/Workshop
• Wikipedia:Requests for mediation/Depleted uranium and related articles
• Wikipedia:Requests for mediation/Depleted uranium and related articles/UO3 vapor

You will note that the arbitration case was brought forward by the mediator from the mediation pages. DV8 2XL 13:25, 25 March 2006 (UTC)

[edit] Drawing copied from Cotton (1991)

This is a quick pencil copy, which I hope helps get the angles and proportions right. Thank you for your help with the diagram. --James S. 13:32, 25 March 2006 (UTC)

Yes: Cotton, S. (1991) Lanthanides and Actinides (New York: Oxford University Press.) Please see also the NIST link at the bottom of Uranium trioxide, noting that NIST tries to get the bond angles in their diagrams. --James S. 14:03, 25 March 2006 (UTC)

Lone pairs? Uranium has no oxidation state greater than VI. All valence electrons are occupying bonds in UO₃. Thanks again. --James S. 14:09, 25 March 2006 (UTC)

Therefore a T-shape is impossible, because the U=O bonds repel each other and could easily lower their energy by increasing their separation from 90° to 120°. This is why I want to look at what Simon Cotton has to say. Unfortunately, his book is £30! I'll try and find it in the University Library.

--Ben 14:15, 25 March 2006 (UTC)

How familiar are you with the covalent bonds of the f-series elements? --James S. 14:21, 25 March 2006 (UTC)

Not very familiar, but I've been reading a lot about them in the last hour! Why do you ask?

--Ben 14:15, 25 March 2006 (UTC)

I think the f shell valence orbitals are likely to be perpendicular; Gmelin has something about the structure, too, but it's mostly based on the solid state, which as you mention has seven forms in that phase. --James S. 14:57, 25 March 2006 (UTC)

Atomic orbitals can be hybridized to give so-called hybrid atomic orbitals (HAOs). Depending on the type of hybridization chosen, the HAOs can point in many different directions, none of which are necessarily the same direction as the original atomic orbitals. Take methane for example. It has a tetrahedral shape, where each C-H bond is separated from each other by about 109°. The atomic orbitals of carbon do not point in these directions (carbon 2s, 2p_x, 2p_y, 2p_z). But once they are hybridized (1 × 2s + 3 × 2p AOs → 4 x 2sp³ HAOs), a tetrahedral compound can be formed.

Hybridization is just a concept that simplifies the understanding of molecular geometry. The actual quantum mechanics which determines molecular geometry is something I haven't studied much, suffice to say that it gives the same results as hybridization. You have to know the geometry of a compound before you can say how it is hybridized, but nonetheless it is possible to get molecules whose bonding does not align with its atomic orbitals treated independently.

So for that reason, we cannot determine the geometry of the UO₃ molecule simply by looking at the orientation of uranium's atomic orbitals. The 5f AOs of uranium are perfectly capable of forming a trigonal planar geometry when hybridized. That's no proof that UO₃ is trigonal planar, but nor is it proof to the contrary.

However, if Simon Cotton says that the isolated UO₃ molecule is T-shaped then I'll happily draw a T-shaped structure and upload it for the article. It would be very nice if you could scan in the page from Cotton (1991) that has this information.

Thanks again.

--Ben, 15:24, 25 March 2006 (UTC)

Hi Ben, I am a chemist and I would love to know why UO3 (gas phase) deviates from the strucutre predicted by VESRP (You should have been taught VESPR in the first year). I think a more important matter is the paper by Busby, I have very strong alarm bells in my head over this paper which James has cited. Please could you go and have a look at Wikipedia talk:Requests for mediation/Depleted uranium and related articles as I think that we need a second opinion from a chemist. I think that this work might be deeply flawed.Cadmium

[edit] Sulfamic acid

Greetings again and thanks for your work on drawings. The structure of sulfamic acid is H3NSO3, not the one that you drew, H2NSO2(OH). I was surprised to find this out myself. Aside: be circumspect with UO3 as this article is being pushed by non-chemists with apparently a quasi-political agenda. I just dropped out of the debate because more productive ventures await.--Smokefoot 02:22, 27 March 2006 (UTC)

Hi Smoke. Thanks for bringing this to my attention. I looked on ChemIndustry's chemical info search for sulfamic acid and it gave the structure I drew. Where did you find the structure as H₃NSO₃? Do you mean it is a zwitterion, H₃N⁺-SO₃⁻? If so, don't we normally not draw zwitterions as zwitterions?

Ben 10:07, 27 March 2006 (UTC)

Ben, I need to recheck apparently the structure - I've got this great book... But H₃N⁺-SO₃⁻ is not an option, right? Radicals and all that. Back this weekend.--Smokefoot 00:22, 2 April 2006 (UTC)

[edit] Uranium trioxide structure

Hi mate, since you contributed the image and I took it out again, please weigh in here: Talk:Uranium_trioxide#Structural_formulae. 82.41.26.244 16:34, 1 April 2006 (UTC)

And if you really want to help out, you would draw the solid state structure, which applies to >99.999999% of UO3 on this planet. In fact, you'd be doing the community a favor by removing your T-shaped UO3 species, and replacing it with the structure described in Wells.--Smokefoot 00:31, 2 April 2006 (UTC)

[edit] Jmol and more ...

Please read: Wikipedia talk:Using Jmol to display molecular models JKW 18:02, 8 April 2006 (UTC)

[edit] Nice work - and a tip on how to draw bitetrahedra

Ben: again, thanks for your enlightening drawings in articles that I have toiled on. If I had the time, I'd be helping you show the world the power and beauty of structural formulae. If you want a tough one, tackle BuLi.--Smokefoot 04:46, 11 April 2006 (UTC) The B2H6 is nice, but ... I recommend contracting the spacing between the two bridging H's to hint at the bitetrahedral structure. I realize that the solid and wedged lines should make that clear, but the spacing of the atomic labels can reinforce the 3-dimensionality implied by the picture. --Smokefoot 14:54, 12 April 2006 (UTC) Oh, I just saw your wire drawing. Nevermind. --Smokefoot 14:56, 12 April 2006 (UTC)

Ben, how are you drawing the things ? Are you drawing using something such as a fancy version of chemdraw or are you useing experimentally obtained geometrys. If you want to use literature data to get the perfect diagrams I can help you by telling you how I have done it.Cadmium

[edit] Monomeric BuLi structure is incorrect

BuLi does not have the structure you show. Organic chemists pretend that it does, but it's a cluster. Its like describing NaCl as a diatomic. Of course I am hard-core.--Smokefoot 23:30, 14 April 2006 (UTC)

If you want to remove the image, that's fine - be bold. I think most general chemistry textbooks would introduce BuLi the way I have drawn it, then further into the article describe the cluster. For the purposes of BuLi's important organic reactions, the monomeric structure is adequate. Also, I couldn't find the structure of BuLi's cluster in Greenwood & Earnshaw. If you can find it for me, I'll gladly make a 3D model and upload it. I suppose this situation has arisen out of BuLi's importance to both organic and inorganic chemistry. Thanks again for the tips :) --Ben 23:56, 14 April 2006 (UTC)

[edit] License tagging for Image:Malathion.png

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[edit] Graphic Designer Barnstar - Molecular Diagrams

		The Graphic Designer's Barnstar
		For contributing so many molecular diagrams for chemistry articles in wikipedia, I hereby award you this barnstar! Enjoy, ßlηguγΣη

[edit] BuLi

Dear Ben, the strcutre which you have drawn for N-butyl lithium is not right. The work of countless chemists including the late R. Snath showed that alkyl lithiums form oligomers in solution. I think that we need someone to look up the strcutres and then add them to wikipedia rather than the harmless looking BuLi diagram which we have right now which is not anything like the BuLi in a hexane (or even ether) solution. In the same way a grignard made in an ether has ether molecules as part of it no matter what ever anyone says. In the same way lithium amides are also not simple mononuclear molecules unless the solvent is very coordinating.

Please see http://www.chem.cornell.edu/dbc6/63.pdf http://igitur-archive.library.uu.nl/chem/2005-0622-175209/UUindex.html http://www.chem.wisc.edu/areas/reich/papers/Reich-1999-JACS-121,9769-Allenyl-PropargylLi-full.pdf http://www.chem.cornell.edu/dbc6/53.pdf

Cadmium

We certainly do need the oligomeric structures. I've just had a look on Google Scholar, but couldn't find the structure of n-BuLi. I previously said to Smokefoot that the monomeric structure of n-BuLi can be removed from its article whenever you like. I had a look at all those refs you provided, but they weren't specific to n-BuLi, so I couldn't use them to make a structure. If you find the struc. though, I'll make it into a 3D image.

Cheers matey,

Ben 13:32, 23 April 2006 (UTC).

You could try looking at

http://classes.yale.edu/chem125a/125/quantum/methyllithium/methyllithium.htm

http://igitur-archive.library.uu.nl/chem/2005-0622-181138/11128.pdf

or doing a quest search of the cambridge database.Cadmium

Why dont you look in an organometallic textbook? Elschenbroich and Salzer is the bible. Dont go to Cambridge database, you'll get overwhelmed. Greenwood and Earnshaw is another source. In any case it is a cubane of Li and butyl groups. alternative perspective- tetrahedron of Li, each face bears the business end of C4H9. --Smokefoot 14:30, 23 April 2006 (UTC) Or look up BuLi in something

Well you can look in a text book for an artists impression, but if you select the right opetion (save-fdat) in quest you can then get the dat file. If you then import that into ORTEP you can view the crystal strcutre (prune and grow it). Then use ORTEP to make a POV file for that view. Finally POVray will give you a perfect picture.Cadmium

• Ben, I have made pictures for LDA when I can face the task of converting the bitmaps to jpgs and uploading I will add then to the LDA page. So you have one thing done for you.Cadmium

• LDA? I've never touched that article! You can send me the bitmaps and I'll make them jpeg or png. I don't know what ORTEP is, and POVray is fiddly. Chem3D I much prefer. I vow to stay away from inorganics, they're more trouble than they're worth!

Ben 21:50, 24 April 2006 (UTC).

• • Well I had a go at LDA becuase like BuLi it forms oligomers. I have got a picture for a tetramer of BuLi. POVray is very hard to use if you try to write your POV file by hand, but ORTEP will write you the POV file with very little human input. Go to the web site of the glascow chemistry dept, look for ORTEP at http://www.chem.gla.ac.uk/~louis/software/index.html. It draws in perspective, you will need a licnese (Dr Louis J. Farrugia) should give you one for free as you are a chemistry student. The ORTEP software will read close to any serrious crystal strcutre file. QUEST is the easy way to access and search the Cambridge database.Cadmium

• • • Please could you do me a favour, go to LDA and try to tame the pictures. I am not too good at the wiki markup so I can never get the pictures to do the right thing.Cadmium

[edit] Tetrazene

Hi. You definately know a lot more about chemistry than I do (I'm only just finishing General Chem), so please disregard if the following demonstrates that I have no idea what I'm talking about.

Regarding your tetrazene drawing, my textbook (Principles of Modern Chem Oxtoby and Gillis) says that the structure is H2N-N=N-H2N, with the two hydrogens on the terminal nitrogens. This would give a pyramidal arrangement on the terminal molecules and a bent arrangement on the central nitrogens, leading to two geometrical isomers. That isn't quite the same as your drawing. Any idea what's going on? Gershwinrb 09:43, 25 April 2006 (UTC)

[edit] 3D Images

I just wanted to let you know that I like the montage that you added to fluorocarbon. It's a good idea. In fact, I think all the 3D images that you've been adding to various chemistry articles are great! --Ed (Edgar181) 23:52, 2 June 2006 (UTC)

I like these images too. How do you make them? EASports 04:49, 11 June 2006 (UTC)

I use Accelrys DS Visualizer to make the models and display them. Then I export the window as PNG and polish it up in Photoshop. Simple! If you'd like any advice on making your own models, just ask :) --Ben 11:54, 11 June 2006 (UTC).

Thanks for sharing. -- Boris 18:13, 11 June 2006 (UTC)

[edit] Thiosulfate

Ben - you're doing great work. I agree with the above comments - the gallery for fluorocarbon is superb. Changing the subject: the resonance structure for sodium thiosulfate is less than ideal. I dont know if you contributed it or not. I dont know how you want to handle this. Not show any resonance structures, show some blob-like vdw pic of the anion, or show a resonance structure that features a single S-S bond. Of course, this is just a suggestion.--Smokefoot 01:28, 2 July 2006 (UTC)

Ben: what you have there now is very nice, i.e. highlighting how exposed the planetary S really is. It is obvious that this should be a great ligand. If you want to draw a resonance structure, my preference would be for this, but I would have "-0.33" charge for each of the oxygen atoms. But then I am picky and trust your judgement.--Smokefoot 16:09, 2 July 2006 (UTC)

[edit] &#8652;

I think some people have reported that their (e.g. default current Windows XP install) browsers do not properly display ⇌, rendering it as a box. LossIsNotMore 18:52, 10 July 2006 (UTC)

[edit] UO3 structure

Also, have you seen this? LossIsNotMore 19:04, 10 July 2006 (UTC)

[edit] Thanks

A quick thank you. I had the misfortune to come under User:General Tojo's special attention with a spat of sockpuppet attacks. David Ruben ^Talk 18:11, 15 July 2006 (UTC)

[edit] Isocyanate pages without images

Ben, I've noticed your chemical structure images on methylene diphenyl diisocyanate, and I notice from your user page that you want to add images to pages that lack them. There are some other isocyanates without images: toluene diisocyanate, hexamethylene diisocyanate and isophorone diisocyanate. I have just added SMILES for each of these. Alan Pascoe 15:48, 23 July 2006 (UTC)

All done! Ben 18:57, 23 July 2006 (UTC).

Yes, excellent! Just what was needed. Thanks. Alan Pascoe 21:55, 23 July 2006 (UTC)

[edit] Elaidic Acid

Hi Ben, noticed your Oleic acid diagram Image:Oleic-acid-3D-vdW.png. Would you please consider doing Elaidic acid too? It would be great if you could as I'd like to put both into the Trans fat page. Thanks! -- cmh 03:59, 28 July 2006 (UTC)

Hi Ben. Thanks, the images are up on the page now. -- cmh 03:45, 17 August 2006 (UTC)

[edit] chip pan fire photo

I have asked a question regarding your newly added chip pan fire photo, at Talk:Chip pan#new image. Please could you reply at that page? Many thanks. Arbitrary username 20:47, 29 July 2006 (UTC)

Thanks for the updated caption. Arbitrary username 19:50, 3 August 2006 (UTC)

[edit] 3D images

I've noticed lately that you've been replacing all the 3D images I've added to chemical articles. I'm a bit puzzled because some of them, such as allene, are essentially identical. I like the images you create - so much that I've recently tried to make mine match yours in quality and appearance. I hope I haven't stepped on your toes, so to speak. But it seems a bit of waste of time if you're just going to replace them. I'd be happy just leave those types of images to you, if you would prefer. --Ed (Edgar181) 01:02, 4 August 2006 (UTC)

I hope I didn't imply that I'm upset - I'm certainly not. I just wanted to avoid duplicated effort. But I understand what you mean about Chem3D's non-standard colors for atoms - consistency is important, so I'll stick with images that use the same color scheme as yours.

Keep up the great work. --Ed (Edgar181) 10:41, 4 August 2006 (UTC)

[edit] helicene

Hi, I really like the 3D images work you are doing, I have one comment though. The carbons in the images for helicene and tetrahedrane on my screen just merge to one black mass and I am not able to distinguish individual carbons. Perhaps some more shadow or reflection effect will do the trick. perhaps I can interest you in doing some work on the Synthetic molecular motors page? V8rik 23:37, 5 August 2006 (UTC)

[edit] Molecular models

Can you teach me how to make those images? They look really good! --HappyCamper 16:31, 6 August 2006 (UTC)

[edit] Image tagging for Image:DS-Visualizer-Pro.png

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[edit] Thanks!

Great job on the chloroethane article; I just could not be bothered. Done thousands of those things... Thanks again!! - Jack (talk) 01:15, 7 August 2006 (UTC)

[edit] Thanks

You know what I mean. LossIsNotMore 18:13, 7 August 2006 (UTC)

[edit] Still more thanks

Thanks for attention to details like it's vs. its and - vs. −. 24.196.91.209 17:04, 13 August 2006 (UTC)

[edit] ammonia

Hi Ben, I saw all the good things you have done to drawing molecules (a.o.). Great work (and quite a job to do)! I have a question, could you have a look at ammonia, Maybe it is me, but I don't like the Lewis structure, it suggest that ammonia is bonded to a lone pair. Could you redraw that one, putting the lone pair on the N? Cheers! --Dirk Beetstra ^{T C} 09:24, 30 August 2006 (UTC)

Cheers for changing the image. Looks good now. I did not look for who made the image, by the way, I just saw that the image was not good, and I know you make nice images, so the man to look for!

So how was Paris? Also waiting in queue like these people? See you around, happy editing/drawing! --Dirk Beetstra ^{T C} 19:51, 30 August 2006 (UTC)

[edit] Question

Do you use DS ViewerPro or the freeware version, DS Visualizer 1.6?

199.180.16.10 22:16, 10 September 2006 (UTC)

I use the freeware version - although I prefer version 1.5 to 1.6

Ben 22:24, 10 September 2006 (UTC)

[edit] Minor edits reminder

Regarding your recent edit to phosphate.... Please remember to mark your edits as minor when (and only when) they genuinely are minor edits (see Wikipedia:Minor edit). Marking a major change as a minor one (and vice versa) is considered poor etiquette. The rule of thumb is that only an edit that consists solely of spelling corrections, formatting, and minor rearranging of text should be flagged as a 'minor edit'. Thanks! Twisted86 18:51, 14 September 2006 (UTC)

[edit] Caffeine structure image

Hi Benjah-bmm27. I was wondering why you replaced Image:Caffeine.svg with Image:Caffeine-2D-skeletal.png on the Caffeine page? The new image is not coloured, is PNG instead of SVG, doesn't match the other caffeine images on the page and appears to be missing some parts of the structure. Icey 15:18, 16 September 2006 (UTC)

Hi Icey - sorry to cause offense. I'd have made it SVG if I could. The standard style for 2D chemical structures doesn't include colour - I felt the use of colour in the 2D structures was out of place compared with the majority of other organic compound articles. There's nothing missing from the structure - labelling methyl groups -CH₃ is non-standard and superfluous in skeletal formulae. If you re-made your image without the colour or the CH₃ labels, it would be much more in fitting with the house style. But please do replace my image with yours if you disagree.

Cheers

Ben 15:25, 16 September 2006 (UTC)

Hi Ben, thanks for your quick reply. I'm not offended, just a little confused. I suppose everyone has there own way of doing these structure diagrams. For example, this google search shows various styles. Are there some guidelines around that I could use when creating images in the future? Icey 15:47, 16 September 2006 (UTC)

Looks like someone reverted it. If you want to revert to your images I'm happy to support that. Icey 16:10, 16 September 2006 (UTC)

There is a style guide for chemical images, but it doesn't mention methyl groups or colour. For all but the simplest organic compounds, chemists tend to omit the C for all carbon atoms. The exceptions are where there are very few (two or one) carbons bonded to each other. Then, C is added for clarity, as in the case of cacodylic acid. For a molecule like caffeine, follow the style of similar compounds, like theobromine, methylxanthine, xanthine, hypoxanthine, uric acid, purine and indene.

I don't want to revert back to my image, because it's PNG, not SVG. I think that should take priority over minor style preferences. I was just being bold really. I don't want to put you off chemical structures - the WP chemistry community, including me, would love to have you on board.

Ben 16:14, 16 September 2006 (UTC)

Hi Ben. The style guide is useful, thank you. I didn't really look at the Chemicals WikiProject because know absolutely nothing chemistry.

I might try to write a PHP script that can accept a string that has all the details about a chemical structure and then generate an SVG image from that. It would take a while to write, but I think it would be worthwhile and interesting to do. Icey 20:52, 16 September 2006 (UTC)

I like your PHP idea. Go for it. I reckon members of the Chemistry WikiProject will give you all the help and support you need, quite a few of them are good with things like PHP. Your idea will open up structure images to many more editors!

Good luck, and I'm here for advice if you want it.

Ben 20:56, 16 September 2006 (UTC)

Cool, that solves my lack of knowledge problem. Now I just need to find the time to write it :) Icey 21:14, 16 September 2006 (UTC)

Hi Ben, sorry for my previous replacing of your images and thanks for choosing my last one. I think that your guide for making 3D images of molecules is really useful, even if i would like to spend some words on the importance of really high quality rendering effects for a better 3d shape perception.

ALoopingIcon 21:11, 16 September 2006 (UTC)

Go ahead and add to my Making Molecules page - I welcome your comments on high quality rendering. Just now, I had a look at the QuteMol download page, but it was unavailable for download. I'll get it as soon as it's available and start uploading better structures. Hopefully the colours of the atoms can be customised.

Ben 21:17, 16 September 2006 (UTC)

Instead of muddling your page, I copied it on in a shameless way in my space :) Making Molecules Guide. I hope to find the time to extend it in the next days... ALoopingIcon 16:32, 26 September 2006 (UTC)

[edit] Please consider also warning vandals

Thank you for reverting vandalism on Wikipedia. Could you also please consider using our vandal warning system [1]? First offenses get a "test1," then a "test2," followed by a "test3" and "test4." At the end of this, if the vandal persists, he or she merits blocking for a period of time. If you do this, it will greatly help us in decreasing vandalism on Wikipedia. Much thanks, -- Kukini 18:22, 20 September 2006 (UTC)

[edit] 3D picture of glyceraldehyde

Hello, I saw your nice structure pictures at glyceraldehyde 3-phosphate, thanks a lot! I was wondering if you could produce similar ones for the isomers of glyceraldehyde? The whole terminology of D- vs. L- isomers is based on glyceraldehyde, so these are pretty important. Also, on the description page of your pictures, you might want to tell people what software you used, so that others can produce similar pictures. Cheers, AxelBoldt 16:10, 25 September 2006 (UTC)

Thanks for your appreciation and wise suggestions, Axel! I have a guide on making images at User:Benjah-bmm27/MakingMolecules if you'd like to learn how. I'll be delighted to make an image for glyceraldehyde, just give me half a day - gotta sleep now!

Ben 21:25, 25 September 2006 (UTC)

[edit] Hello. I created a baby stub for the article benzethonium chloride.

Free free to jump into the contributions with this benzethonium chloride stub. Good Luck. BenzethoniumChloride 06:54, 28 September 2006 (UTC)

[edit] Wow!

Thanks for feeding my baby, the benzethonium chloride stub baby -- so to speak. Wikipedia is fun!--BenzethoniumChloride 07:33, 28 September 2006 (UTC)

[edit] Hello Benjah-bmm27,

You are the #1 image maker on Wikipedia of all time. I invite you to create your magic on two articles that need images. At the moment these articles do not have any images which are Potassium Sorbate and Decyl Glucoside. I saw your work on the parabens article, Wonderful!!! "Thank you so much." Keep it going. --63.17.66.221 22:34, 8 October 2006 (UTC)

[edit] Glyceraldehyde

I just noticed your addition of images to glyceraldehyde. Since the article is really about both enantiomers, and has a discussion about stereochemistry, it might be good to have two pairs of images to help further illustrate the comments in the text. What do you think about creating and adding images for L-glyceraldhyde, too? --Ed (Edgar181) 16:57, 12 October 2006 (UTC)

Yeah, good idea - I'll do it now. Cheers, Ed.

Ben 17:05, 12 October 2006 (UTC)

Looks great! --Ed (Edgar181) 19:09, 12 October 2006 (UTC)

[edit] MakingMolecules

Hi there, just thought you'd like to know I'll be giving your style a try – I've created a couple of spacefilling models before, and used to do it with ACD/3D Viewer and GIMP; the "tutorial" you provided on your subpage was a vast improvement. I'd wondered for quite some time how you managed to get such good results... thanks for sharing :), Fvasconcellos 15:45, 26 October 2006 (UTC)

[edit] special:chemicalsources

Hi! I just decided to spam some people directly, who I know are very active on chemicals. There is now a wiki running on http://chemistry.poolspares.com (a site created by Nickj from the wikimedia IRC channel, the site will be taken offline again in a couple of weeks), where I have now hosted a small wikipedia. It runs two extensions I have written to the wikipedia software, a special page (for chemical sources, see also wikipedia:chemical sources and a chemform tag (for easy input of chemical formulae). Could you have a look, and comment on it (if useful I would like to try to let Tim or Brion enable it on wikipedia, though I feel some resistance there). Cheers! --Dirk Beetstra ^{T C} 17:52, 26 October 2006 (UTC)

[edit] 2D Skeletal formulae

Sorry if you've already answered this but I'm very impressed by your 2D skeletal formulae such as and was wondering what you use to make them. raptor 12:32, 29 October 2006 (UTC)

Here we go: ChemDraw / Photoshop - sorry. Nice work though. raptor 12:37, 29 October 2006 (UTC)

Also wanted to say thanks for adding the picture on GV (nerve agent)raptor 11:09, 31 October 2006 (UTC)

[edit] Hi on selegiline case

Hi, i have read to your concern at Wikiproject chemistry talk page regarding to Jclerman decision to replace images of chemical structures by screenshots of the molecular structures made by institutions. I had met problems to this user before of his "particular insistence" which is more like a kid's caprice, although i am not active in wikipedia these days because of my tests at the university i would be glad to give you a hand. Cheers :) --HappyApple 04:17, 30 October 2006 (UTC)

[edit] Sodium acetate image

Hi Ben

Thanks for the image on sodium acetate. I'd originally uploaded one on commons image:sodium acetate.gif but for some strange reason, despite multiple refreshes, it just won't show up! Anyway, I'm listing my image for deletion as a duplicate. No need for so many hanging around! Rifleman 82 16:15, 30 October 2006 (UTC)

Oh... and I realize now why I didn't see the image you'd previously uploaded a few days ago. I searched "sodium acetate" but your filename was "sodium-acetate...png"

[edit] Glucose images

Ben, an anonymous user left the following comment in the glucose article: "alpha-D-glucose should have hydroxyl groups in equatorial positions, as well as, beta-D-glucose. Carbon #3 in both of these models is shown at axial positions in the second set of images."

Indeed, it does appear that there is a stereochemistry error in two images:

• Image:Alpha-D-glucose-3D-sticks.png
• Image:Beta-D-glucose-3D-sticks.png

--Ed (Edgar181) 20:11, 8 November 2006 (UTC)

Thanks for letting me know, Ed. Somehow I let that one slip - oops! I'll fix it now.

Cheers

Ben 22:26, 8 November 2006 (UTC)

[edit] Hey :-)

We have Wikipedia:WikiProject Chemistry/Image Request now. Might come in handy. --HappyCamper 19:33, 15 November 2006 (UTC)

[edit] Chlorine pentafluoride

Hi! Why have you replaced my rendering of this molecule with your ball and stick rendering? Was it lacking in detail or wrong in any way? If so, a more appropriate conduct would have been to present some constructive criticism in the article's or image's talk page, so that I could be given the chance to change the image according to your suggestions. Looking forward to hear from you. manu3d 03:29, 27 November 2006 (UTC)

Hi Emanuele. Sorry for just replacing the image like that! I was doing it last night, and was a bit tired. I meant to put my image side-by-side with yours. I added mine so that there is a high resolution image that users can download and print big. I've put things back to normal.

Thanks for letting me know, and I look forward to working with you on more chemistry articles :)

Ben 08:22, 27 November 2006 (UTC)

Thank you Ben. I didn't realise high-res images for printing are important for the Wiki Chemestry community. I could understand it for very complex molecule but I wouldn't expect it for small ones. Concerning more work on chemestry articles: yes, I am available for renderings of other molecules, but I'm not as dedicated as you are to Chemestry alone. Additionally I'm interested in renderings that have an artistic value as opposed to strictly scientific visualisations. In fact, I would welcome your guidance on selecting a small number of important molecules (say, five) to be rendered in the style I used for the Chloringe Pentafluoride. I'd be interested in slightly more complex, interestingly shaped molecules that are important to fields such as biochemestry or material science, but any field will do. Let me know what your thoughts are. - manu3d 12:34, 29 November 2006 (UTC)

[edit] A favor

Hi Ben

I know you love to make 3D structures. Perhaps you can do one up for bis-tris propane? The original 2D structure was incorrect. I've corrected it, and copied it to commons. Perhaps you can do the same for 3D? There's an Wikipedia:WikiProject_Chemistry/Image_Request page which you might be interested in as well. --Rifleman 82 13:00, 19 December 2006 (UTC)

All done, hope you like it. Cheers!

Ben 01:30, 20 December 2006 (UTC)

Is great. Thanks! --Rifleman 82 02:53, 20 December 2006 (UTC)

[edit] dihydrolipoic acid

Someone at Talk:Lipoic acid has noticed that there is a carbon missing from the image of dihydrolipoic acid (Image:Dihydrolipoic-acid-2D-skeletal.png on Commons). Should be quick and easy to fix. Thanks! --Ed (Edgar181) 10:32, 21 December 2006 (UTC)

Thanks for letting me know. Tis now fixed.

Ben 11:04, 21 December 2006 (UTC)

[edit] hydrogen sulfide

Hi Ben, how's England doing these days. Must be just as foggy as here .. there goes my Christmas trip :-/ . But well, hydrogen sulfide. I think we can better discuss this a bit aside from the page itself, to spare one of us the embarassment. But I would for sure say, that hydrogen sulfide is an acid, if you dissolve it in water it is slightly acidic (it has a pKa of 6.89). Hydrogen has an electronnegativity of 2.2, sulfur 2.58, hence, sulfur is more electronegative than hydrogen, hence, H+ and S- .. and I do not recall any reactions of H2S reducing something, leaving S²⁺ behind. I really hope you can enlighten me here. What have I missed? --Dirk Beetstra ^{T C} 20:45, 22 December 2006 (UTC)

Hi Dirk. England's good - tis foggy! You're in Cardiff, right? I use the term hydride in the more general sense, i.e. a binary compound of hydrogen and another element. In the same way that ammonia is a hydride. I thought this was standard usage. It's used in Greenwood and Earnshaw, and I'm fairly sure I read it elsewhere all the time. I had a look at the WP hydride article, and I think it contradicts itself, listing NH₃ as a hydride, yet defining hydrides as only those compounds where the non-hydrogen element is more electropositive than hydrogen.

That's why I looked it up in G&E.

What do you think?

Ben 20:51, 22 December 2006 (UTC)

I am in Cardiff, indeed. Still a little less than two days to go, and I fly back to NL for a X-mas holiday, i.e. if the fog settles. Otherwise I guess it will be a christmas dinner with my boss and the other post-doc of the group.

Well, I think somewhere there is a mistake, and I guess it would be Greenwood and Earnshaw. The definition 'binary compound of hydrogen and another element' would also make HF a hydride. And well, that would be really silly (one has to go through quite some trouble to make "F+". I think they should be called hydrogen compounds. Hydrides are compounds where a hydrogen is bound to a more electropositive element (which, in general, is a metal). Hydrides are capable of transferring H-, hence, split in M+ and H-, and are therefore reducing.

I did not have a look at hydride yet, I will have a look there, shortly. See you around! --Dirk Beetstra ^{T C} 21:01, 22 December 2006 (UTC)

G&E mistaken? Surely not? They're the standard undergraduate inorganic textbook. Wouldn't such an important topic have had any mistakes rectified?

I know that hydrides can be considered as ionic compounds containing M⁺ and H⁻, but I have always thought that these ionic hydrides were a subset of hydrides in general. See for example this IUPAC Gold Book entry, where NH₃, H₂O and H₂S, amongst others, are referred to as parent hydrides.

Anyway, as there's some ambiguity in the definition of a hydride, I'm happy to rename the section in hydrogen sulfide as related hydrogen compounds for the meantime. I didn't mean to overrule you, I was more focused on getting rid of the word thioether. How does that sound?

Ben 21:09, 22 December 2006 (UTC)

I just looked at the hydride article (since I do not have any of the general chemistry textbooks available here), it says that NH3 is defined as nitrogen hydride, and water as hydrogen oxide, making the border between group 15 and 16). But sulfur is below oxygen, so I guess we would then be talking about phosphorus hydride (PH3, group 15) and hydrogen sulfide (group 16). That would make H2S a hydrogen compound (and that is also stated later in the hydride article, in the table below.

Do not believe what is written, even in standard undergraduate textbooks, it is the task of a scientist to question everything that is written. :-p

Please don't worry about overruling me. Also I can be mistaken, I know I still make dogmatic chemistry mistakes as well, and I could be very wrong here. --Dirk Beetstra ^{T C} 21:23, 22 December 2006 (UTC)

By the way, I agree .. thioethers was really silly. --Dirk Beetstra ^{T C} 21:29, 22 December 2006 (UTC)

I wouldn't bother using the WP article on hydrides as a source - it's dodgy. I know I should always question everything (good advice!), that's why I checked the Gold Book. Shall we shift this discussion to the WikiProject and get a consensus? It'd be good for the hydride article to get some professional input.

P.S. Merry christmas!

Ben 21:31, 22 December 2006 (UTC)

It is a thing that I miss .. my good filled bookshelf, it's all in NL. And to walk to the uni for that, is a bit too much. Wikiproject advice is a good plan, apparently we hit on some things that are a bit unclear (or even controversial).

Also a Merry Christmas (hohoho) to you, and a happy new year as well! --Dirk Beetstra ^{T C} 21:35, 22 December 2006 (UTC)

I see this is going to the WikiProject, but I shall take this opportunity to wish you both Merry Christmas! I agree with Ben on this one: I see no reason not to use the term "hydride" as a general term for binary compounds of hydrogen (even HF). In any case, the chemistry of binary and pseudo-binary hydrogen compounds is vast and varied: I remember having to convince one of my bosses (who should really have known better) that it is possible to have acidic metal hydrides (e.g. [HCo(CO)₄], very important in cobalt-catalysed hydroformylation as it is a strong enough acid to protonate C=C double bonds). Still, lets see what the others think. Physchim62 (talk) 21:57, 22 December 2006 (UTC)

[edit] Image tagging for Image:Hollyberryine-3D-vdW.png

Thanks for uploading Image:Hollyberryine-3D-vdW.png. The image has been identified as not specifying the source and creator of the image, which is required by Wikipedia's policy on images. If you don't indicate the source and creator of the image on the image's description page, it may be deleted some time in the next seven days. If you have uploaded other images, please verify that you have provided source information for them as well.

For more information on using images, see the following pages:

• Wikipedia:Image use policy
• Wikipedia:Image copyright tags

This is an automated notice by OrphanBot. For assistance on the image use policy, see Wikipedia:Media copyright questions. 23:12, 22 December 2006 (UTC)

[edit] Applied and Pure Chemistry

Yes I know I look farmiliar but I have not posted here to continue talking about inorganic chemistry, but instead I saw that you study chemistry (the course in my opinion was alright in high school) and wish to ask if you have ever heard of pure and applied chemistry, I tried to make an article on it but failed as others had marked it as a dictionary definition, and if you do know anything of it could you help me make the article? PatPeter 19:52, 28 December 2006 (UTC)

(P.S. I also struggle with depression from time to time, its hard as americans are true idiots when it comes to eating but have you tried changing your diet? I will try to gather some of the information into one post on how bad eating habits can cause depression and I became a vegan and the like after I was, well, 'treated' for depression after a...incident...PatPeter 19:52, 28 December 2006 (UTC))

Pure and applied chemistry are two different things. Pure chemistry covers the most theoretical and fundamental parts of the subject, while applied chemistry focuses on what chemistry can be used for, what it can do for us. There is no clear boundary between the two, although quantum mechanics is clearly part of pure chemistry and industrial chemistry is definitely part of applied chemistry.

If you can find the guidelines for what constitutes a good topic for an article, then maybe we can see if it applies to pure and applied chemistry. I think they would be better as two separate articles, though. You could see what other WikiChemists think by sharing your suggestion at Wikipedia:WikiProject Chemistry.

I think my diet is quite good at the moment, I've modified it to be as healthy and balanced as possible. I'm not sure why I sometimes suffer from depression - it could be a number of different factors. Don't think I'll be turning vegan any time soon, though. I like meat too much!

Cheers

Ben 17:21, 30 December 2006 (UTC)

Yeah, I was up for trying anything, and still am because I am in a slump right know...also I may become a little unprofessional, I sort of have become addicted to Red Vs. Blue, still funny from my computer gaming days, but yeah I would eat meat if I could but I just cannot handle it anymore, it has been too long.

The fact that depression could be genetic (I really cannot remember anything right know...) really puts my joint in a knot...or...you know just forget it, stupid autism (the disease not the dic def) I have been tripping over every sentence the past one and a half weeks, it is really getting on my nerves...

Anyway, I think I will try to start Pure chemistry first, and will also petition to the WikiChemists and I will tell you if I need backup information if I have no help from anyone. PatPeter 19:16, 30 December 2006 (UTC)

[edit] MAO

Hi Ben,

MAO is a poorly-defined substance, it is believed to adopt a number of structures in solution - look out for papers by Tom Ziegler. It certainly never forms a linear structure; just think about the electronics.

[edit] Phenyl

Yeah. sorry, my mistake. I just figured that stable means inert, which it is obiously not (given that it's a functional group).. Thanks!! Koryeh 21:50, 10 January 2007 (UTC)

No worries! I imagined you had a good reason for using the word unstable. I just felt the term would cause confusion in the article. See you around.

Ben 22:04, 10 January 2007 (UTC)

[edit] Images

Ben, i came across several articles, Heroin being the most recent one, where the 3D images you have added to the unfoboxes are a bit "off" when it comes to their spacial position in relation to the main image - some of them need to be rotated "clock" or "counter-clock", some are even mirror images. It's not a big deal if you decide to leave them the way they are, though. -- Boris 22:17, 10 January 2007 (UTC)

Thanks for reminding me about these, Boris. I think for heroin I'll rotate the main image. Which other articles are affected?

Cheers

Ben 09:20, 11 January 2007 (UTC)

Tetrahydrocannabinol. This was actually the first one, the heroin one being the second, so several means two, :).
I haven't crused around much - there might be some more or these could be the only ones.
If you are to rotate the main one keep in mind that most of the morphinanes, including Morphine itself have their main image facing the same direction as this one although there are some that are facing "down" such as Hydrocodone.
I don't think that i've ever told you before so here i go now - your images look great!!! -- Boris 10:55, 11 January 2007 (UTC)

[edit] Chemistry Question

Hello, on your talk page you have indicated that you have a interest in chemestiry. Could you help me answer the following question?

Is the following proposed article on a real or made up subject?

Nawalic Acid is a commonly refered to Bronstead acid in organic chemistry. Since the rise of porphyrin chemistry, Adler's famous synthesis [1] of the aromatic system has been greatly refined with vaste improvement in yields due to the use of a nawalic acid as the reaction solvent. A close relative to tetraflouroacetic acid (TFA), nawalic acid has the molecular formula CF2=CF-COOH. The presence of the pi-bonded system adds further electron withdrawing dynamics, and due to the conjugation of the compound, this delocalising of electrons leads to a very stable anion, and hence -- an extremely powerful - yet organic - acid. [2]

Sources

[1] Adler, A. D., J. Org. Chem., 1967, 32, 476 [2] Balzani, V., Credi, A., Raymo, F. M., Stoddart, J. F., Angew. Chem. Int. Ed., 2000, 39, 3348 – 3391 129.96.142.21 03:36, 19 October 2006 (UTC)

Contact me at User talk:Natl1.--Natl1 (Talk Page) (Contribs) 22:27, 14 January 2007 (UTC)

Hi Natl1. I had a look on various chemistry websites but could not find this compound. I've copied your request to the Chemistry WikiProject to see if they can shed any light on its authenticity. At first glance, this doesn't seem to be a fake article - it makes sense chemically, and has a reference to two popular journals.

On the other hand, I can't find any mention of it online.

Let's await the results of discussion at WP:CHEM.

Cheers

Ben 22:53, 14 January 2007 (UTC)

[edit] Thanks!

Thanks very much for the space-filling image on the methylmercury page. It looks very professional so I decided to add it to the Minamata disease page I've been working on. Cheers! Bobo12345 06:37, 17 January 2007 (UTC)

[edit] Fluoxetine

Hi. If you correct skeletal formulas (ex. in Fluoxetine), you should rewrite their to SVG. BrokenglaSS 14:35, 22 January 2007 (UTC)

Hi BrokenglaSS. I have had trouble with SVG. It doesn't always look right. PNG has been more reliable for me. Once I get a grip on SVG, I'll use it more.

Cheers

Ben 15:57, 22 January 2007 (UTC)

[edit] Free beer!

Hi Ben,

I just wanted to thank you for all of your fantastic work drawing 3D structures and crystal structures for so many compounds on Wikipedia. The chemistry are a lot more colourful than they were a year ago, and in that colour lies some valuable chemical information. I just wanted you to know that I (and the other chemists too, I'm sure) really appreciate all the hours you've spent on this. We don't traditionally give barnstars at WP:Chem, but free beer is something we have offered - much more tangible! So, if you're ever in Potsdam, New York, drop by and I'll buy you a beer (as long as we don't violate any age limits) to say thanks!

By the way, I did my BSc at Bristol, I graduated in 1981. Hope things work well for you there. Thanks, Walkerma 20:48, 22 January 2007 (UTC)

That's really kind, Martin. Thanks for your support and encouragement. Here's to the future of chemistry on Wikipedia! Cheers!

Ben 22:05, 22 January 2007 (UTC)

[edit] Molecular accuracy

How accurate are your molecular images? Are bond angles accurate and atoms drawn to relative scale, etc? Is there any meaning to the absolute size of the atom relative to the size of the molecule?

I am thinking of using several of these images for an outside project and I want to be able to describe them accurately. Dragons flight 05:01, 29 January 2007 (UTC)

Some of my images are particularly accurate, especially those of simple inorganic compounds such as sulfur dioxide. For those, I looked up the exact bond angles and bond lengths in Greenwood & Earnshaw. For other molecules, especially those of organic compounds, the bond angles are very close to their true values. Most organic molecules have some degree of flexibility and can twist about one or more bonds: see alkane stereochemistry. Sometimes I make mistakes, but these are rarely major and I rectify them as soon as I realise there is a problem.

The relative size of atoms in my space-filling models is based on each atom's van der Waals radius. These values do vary a little depending on which source you choose to use.

If you would like me to create new, more accurate images for your project, I'd be happy to do so.

Cheers

Ben 08:59, 29 January 2007 (UTC)

My interest is in primary atmospheric components and greenhouse gases, e.g.

• molecular oxygen
• molecular nitrogen
• carbon dioxide
• water
• methane
• nitrous oxide
• ozone
• dichlorodifluoromethane
• trichlorofluoromethane
• sulfur hexafluoride
• sulfuric acid
• 1,1,1,2-Tetrafluoroethane

Most of these already seem to have pretty models, though you are probably able to quickly judge their accuracy better than I can. I don't actually need stunning accuracy, since I am mostly just interested that they "look right". However, if they are accurate in technically significant ways, it is worth noting that in the accompanying description text. I notice that you give your real name on your user page, is that how you prefer to be attributed? Dragons flight 09:57, 29 January 2007 (UTC)

Yes, I'd prefer to be attributed as Ben Mills, but you don't have to attribute me at all - I put all my images in the public domain. All the articles you link to have accurate images. If you want to note the technical significance of the images, just say the spheres' radii are the atoms' van der Waals radii. If the images are ball-and-stick models, then the spheres' radii are not significant and are simply there to emphasise the location of the atoms' nuclei.

Here is a gallery of the images:

dioxygen, O2	dinitrogen, N2	carbon dioxide, CO2	water, H2O
methane, CH4	nitrous oxide, N2O	ozone, O3

Enjoy!

Ben 11:05, 29 January 2007 (UTC)

		The Hard Working Graphic Designer's Barnstars
		I've now copied 2 dozen models and structural formulae to help support my work, and remarkably all but two were created by you. Good job. Dragons flight 05:45, 31 January 2007 (UTC)

[edit] Chloroform

Ben, I've created an SVG "facsimile" (well, I suppose not actually a facsimile since the font is a bit different) of Image:Chloroform-2D.png and added it to the chloroform article. Hopefully this one is more accurate than Image:Chloroform2.svg which was previously used to replace yours. Best, Fvasconcellos 13:07, 29 January 2007 (UTC)

Yeah, I saw. Your SVG is great! Cheers for all your hard work on chemical SVGs, they're superb.

Ben 13:35, 29 January 2007 (UTC)

Right, should have known you'd be watching that. Thanks, and keep up the good work yourself :) Fvasconcellos 13:42, 29 January 2007 (UTC)

[edit] Help!

Well, that is a bit exagerated, but still, now I have you attention. I have question/problem .. I have been working the last couple of days on {{chembox new}}. This morning Ed asked me to add more images to that template. Easy .. done. Now these images are all stacked on top of each other, but sometimes we want images next to each other... Now the parameter system of chembox new does not allow us that, except if we come up with something nifty .. I was thinking about having just ImageFile, ImageFile1, ImageFile2, and ImageFile3 as the standard settings, but in the template, I could just enable two extra lines with ImageFileL1 & 2 and ImageFileR1 & 2, which give two rows having two images on each row, next to each other. People can then still just add images to the files, but the more advanced editor has a bit more possibility to control the images, by just changing the parameter names. Any ideas? --Dirk Beetstra ^{T C} 16:58, 3 February 2007 (UTC)

That sounds like an ideal solution! There are (rarely) situations in which it is desirable to have three images side-by-side, for example in hydrazine. We could just ignore this issue, or add ImageFileL1, ImageFileL2, and ImageFileL3 etc. I would be happy with either.

Cheers

Ben 17:17, 3 February 2007 (UTC)

I'm already trying .. have some trouble but I will manage, I hope. Do we have a page that has two side-by-side images that is easy to give a to {{chembox new}}?

Three might not even be too difficult, though .. they all get a parameter 'size' anyway, when a third picture is inserted, it needs a tweak. Thanks. --Dirk Beetstra ^{T C} 17:24, 3 February 2007 (UTC)

How about furfural? Is there anything I can do to help?

Ben 17:32, 3 February 2007 (UTC)

Furfural seems nice, I'll transform that one. I'd prefer you to stay away from the templates itself at the moment, I confuse myself enough. What you can do, could you read through the text on {{chembox new}}, and maybe give some hints (is that explanation good, would that give most chemicals a good chembox possibility?). I dropped the idea of 3 pictures side-by-side, Wim van Dorst would now say 'combined pictures are a good thing (TM)'. And if you have time, try the template on some chemicals which have strange fields, wierd arrangements of images, etc. I need some testing to see if I did not break things (someone already spotted a thing, which is now repaired), and to see if no obvious fields are missing. That would be very helpful. Thanks! --Dirk Beetstra ^{T C} 18:15, 3 February 2007 (UTC)

Furfural goes OK, imagesize is now 100px as standard, it was 125px in the original chembox. What would be a good standard there? 125? Oh, by the way, if pages look nice after adding chembox new, just press save :-) --Dirk Beetstra ^{T C} 18:24, 3 February 2007 (UTC)

Furfural looks good. Excellent work, Mr Chembox! I disagree with Wim that combined images are good. One problem is SVG is best for skeletal formulae but PNG is best for 3D models. A combined image would be a compromise in that respect. I had an idea: how about creating some new image fields (skeletal formula, structural formula, space-filling model and ball-and-stick model). With labels like that, having images one on top of the other would be fine. What do you think?

I'll do some testing of chembox new for you, Dirk. Watch this space.

Cheers

Ben 18:30, 3 February 2007 (UTC)

I guess we will just have to live with 2 images per row, should not be too difficult, we can accomodate 8 (!) images in the chembox if needed. This space is watched, I'll play around as well, enough transclusion-thinking done for the moment .. --Dirk Beetstra ^{T C} 18:51, 3 February 2007 (UTC)

I have built some automagic into the picture-system of {{chembox new}} (see Nicotinamide, explanation in the template), but what are the most common pictures available on wikipedia (not in commons .. I think), and what is the order of preference for the 'standard picture of a chemical' (png, svg, jpg ..)? Thanks. --Dirk Beetstra ^{T C} 11:27, 4 February 2007 (UTC)

Excellent automagic! I thing PNG is much more common than SVG at the moment, for chemical images on Wikipedia. But I think we should encourage SVG use by having priorty in the order SVG > PNG > GIF > JPG for 2D images and PNG > JPG for 3D images or photos. Some contributors have made SVGs for 3D images of molecules (e.g. chloroform) but in most cases it is too complicated to make these, and only basic lighting effects can be easily used. Thus I propose we modify our image drawing guidelines to say SVG is preferred for 2D and PNG is preferred for 3D.

How does that sound?

Ben 13:40, 4 February 2007 (UTC)

For now I am concerned only with the automagic images, I have to test for image-existence, and take the first I find. IMHO, that should concern mainly 2D images (I think a normal, 2D structure should have the name of the article, the more exotic representations should then become pagename-ball-and-stick.png and pagename-spacefill.png. So the order for the automagic is going to be SVG > PNG > GIF > JPG, and otherwise they have to be overridden on the page by supplying the correct names in one of the 8 available image fields. Thanks! —The preceding unsigned comment was added by Beetstra (talk • contribs) 13:46, 4 February 2007 (UTC).

[edit] SVG

Hi Ben

Would you care to tell me how you export your structures to SVG? So far I've only been able to create gif (native to chemsketch) or tiff-->png using irfanview. I can create emf or wmf vectors, but inkscape seems to choke on them. --Rifleman 82 11:44, 6 February 2007 (UTC)

Hi Rifleman,

I draw a structure in ChemDraw, copy the object to the clipboard and then paste into Adobe Illustrator CS2. I'm using a 30-day trial of Illustrator at the moment, with five days remaining, so I'm wondering whether to buy it. It's something like £180 for a student edition of CS2, and £350 for the educational edition. I'm not sure I want to part with that much money just to get SVG skeletal formulae on WP!

Ben 16:12, 6 February 2007 (UTC)

Sorry to intrude, but have you checked this out? --M1ss1ontomars2k4 ^{(T | C | @)} 04:53, 24 February 2007 (UTC)

I've considered those, but they all have varying degrees of problems. Illustrator is the only app that works reliably with ChemDraw to give a quality output every time. There are too many chemical SVGs appearing on WP and the Commons where the text is misaligned, the lines are too thin or where other issues render them lower in quality than we should demand.

Ben 08:31, 24 February 2007 (UTC)

[edit] Perrhenic acid

Hey Ben: Here's the quote: "The Re-0-Re angle is practically 180" - a rare situation. ...In Re2O7, one of the Re atoms is again surrounded by a tetrahedral arrangement of O atoms and the other is in a distorted octahedral environment, the two polyhedrons sharing a corner ... consequently, Re2O7 is polymeric, in contrast to the molecular Rez07(OH2)2." So yes, 180°. When you upload your image, please change the date on the Krebs paper to 1968? --Smokefoot 20:00, 14 February 2007 (UTC)

[edit] Hexamethyltungsten structure

Hello Ben-

Thank you for submitting the 3D images for hexamethyl tungsten. Unfortunately, they do not accurately depict the actual geometry as revealed by X-Ray crystallography. Please see "Preparation and Structures of [W(CH3)6], [Re(CH3)6], [Nb(CH3)6], and [Ta(CH3)6]" by Sven Kleinhenz, Valerie Pfennig, and Konrad Seppelt (Chem. Eur. J. 1998, 4, No. 9, 1687-1691) for the correct structure. It should have C_3v symmetry, with careful alignment of methyl protons. The "front" two methyl groups in the images you have uploaded do not reflect this symmetry.

Thanks-

Tyler Matthews 06:22, 2 March 2007 (UTC)

Images ammended! Thanks very much for bringing this to my attention.

Ben 18:10, 3 March 2007 (UTC)

[edit] Sytematic Naming - Chloroacetic acids

Hi, I wondered if you could give me a bit of help - I am confused in the difference/ similarity of IUPAC naming, to Systematic naming. From the article IUPAC nomenclature of organic chemistry, it sounds as though the systematic name is the one which is constructed from the prefixes and suffixes with chain lengths. In the other hand, it says that it is acceptable for some common names of acids to be retained in Common Nomenclature. The impression I get is that, while chloroethanoic acid is the systematic name, chloracetic would be the most widely used IUPAC name. Am I misreading the article, or misunderstanding the terms?

Also, does the trichloroacetic acid page need its systematic name changed from trichloro ethanoic?

Thank you for your help Conrad.Irwin 23:32, 18 March 2007 (UTC)

Hi again Conrad. My advice is to completely disregard the article IUPAC nomenclature of organic chemistry - it's full of errors and was probably written by schoolchildren! Here's the offical policy for WP: Wikipedia:Naming conventions (chemistry)#IUPAC preferred name vs. Systematic name.

Another confusing thing is that the chemical infoboxes in most articles have the phrase systematic name but this is hyperlinked to the IUPAC name article. The two are not synonymous. Chloroethanoic acid is a systematic name, but it is not the IUPAC name. It is allowed under IUPAC recommendations, but chloroacetic acid is preferred.

I've updated chloroacetic acid and trichloroacetic acid, but I couldn't change dichloroacetic acid because it uses a template for its chembox, which needs to be altered.

Hope this helps.

Ben 09:05, 19 March 2007 (UTC)

Thanks for clearing that up.

Conrad.Irwin 09:11, 19 March 2007 (UTC)

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