User talk:V8rik/Archive 06

File:Ter Meer reaction.png

Hi V8rik, in the file above the positive charge of the N in formula 3 is missing. Could you please be so kind to add this? Thanks from Germany --Mabschaaf (talk) 16:50, 11 January 2010 (UTC)

Hi again, have you missed that one? Please correct or comment. Thanks again --Mabschaaf (talk) 15:29, 27 January 2011 (UTC)

It took a long year of preparation (...) but the issue is almost resolved, see for the updated version: File:Ter Meer Reaction.svg V8rik (talk) 18:08, 1 February 2011 (UTC)

Good Afternoon, V8rik

I was looking at our discussion of the Woodward-Hoffmann Rules and noted that somehow we had listed the title as the (4q+2)s = (4q)s rather than (4q+2)s + (4q)a . But then I looked further at my comments which were not clear at all.

What I should have said was that the number of the two terms needs to be odd, since (4q+2)s for 1 3, 5, etc will have 4n+2 electrons with a Hueckel system and be allowed. For this term being 2, 4, 6, etc one would have 4N electrons and a Hueckel system and be forbidden. For the (4q)a term being 1, 3, 5, etc one has a Moebius system and 4N electrons. With the term being 2, 4, 6 etc one has a Hueckel system with 4N electrons. Each "a" component adds one plus-minus node. Thus the 1970 rule really is just a way of paraphrasing the 1966 Moebius-Hueckel method of counting nodes around a cycle. I'm a bit sleepy this afternoon and hope I haven't made an error.

With best regards,

Howard Hez (talk) 20:12, 29 October 2010 (UTC)

• Hi Howard, Our discussion took place on Talk:Woodward–Hoffmann_rules or on this user page? Also, the rule mentioned in the Woodward–Hoffmann rules:

A ground-state pericyclic change is symmetry-allowed when the total number of (4q+2)s and (4r)a components is odd

is a correct representation? V8rik (talk) 22:42, 31 October 2010 (UTC)

for its molecular size it is the most complex substance known

http://en.wikipedia.org/wiki/Strychnine_total_synthesis#cite_note-31

great citation lol

its even better cause that statement directly contradicts the origin of the quote on strychnine's own page --Genya Avocado (talk) 00:11, 27 February 2010 (UTC)

• Better use Talk:Strychnine_total_synthesis for this comment. I do not see a contradiction. Nicolaou cites prog. org. chem., 1952 1, 2 as the Robinson source. Woodward in 1963 is not sure where it came from. The article does not imply Robinson is not the source V8rik (talk) 20:59, 28 February 2010 (UTC)

equilibrium constant

Please look at Talk:Equilibrium constant#time dependence for a detailed answer to your criticism. Petergans (talk) 08:03, 5 April 2010 (UTC)

I hope that the revision of Dynamic equilibrium meets your objections. Petergans (talk) 12:34, 13 April 2010 (UTC)

• Thanks, I have read it, I am happy too see that the point I wanted to make found its way into the thermodynamics section. V8rik (talk) 21:23, 13 April 2010 (UTC)

Chalcohalide

What is a chalcohalide? Is it any element of groups 16 or 17? Is it a compound of elements from group 16 and 17? I can't edit it until I know what the word means. Thanks. --Cheminterest (talk) 23:02, 14 April 2010 (UTC)

Birch reduction

Hi, are you saying you've read the J.Chem.Ed. article and you agree with it? If so, I trust you're knowledge of organic chemistry more than I trust my own. If not, I'll email the authors and ask for a copy, because I don't understand what they're trying to say ;) Physchim62 (talk) 17:55, 19 April 2010 (UTC)

• Yes, the articles that I cite I have usually read. I thought it would make an interesting addition to the article but concerns were raised and therefore the part of the content dealing with it is deleted. Perhaps you can stimulate the authors to participate in the discussion V8rik (talk) 17:42, 20 April 2010 (UTC)

TO V8rik

I hope I am on the right Talk page to contact you.

Thus I have been meaning for some time to write you with an Apology.

I am used to the rough verbiage many of us use in arguing views on mechanistic Organic chemical problems and Organic chemistry in general.

I now see that in Wikipedia, no matter how strongly you disagree with something it is not proper to say anything more than that you disagree with it and that you think it is wrong.

You have been pretty vociferous with me but I can take that, realizing that it has been a result of my criticisms.

I suppose the problem arose mainly when the article I wrote was merged with the one already in Wikipedia. There definitely were things I didn't consider correct. Our views do differ. That should not matter but it has.

In any case, please to accept my apology for being less than restrained.

Wish very best wishes, Howard

--Howard E. Zimmerman 00:43, 22 April 2010 (UTC) —Preceding unsigned comment added by Hezimmerman (talk • contribs)

• Dear Mr Zimmerman, Thank you for your comments, no need to apologize, many things were said in the heat of the debate. Let us try to turn the Birch reaction into a great article! Rik V8rik (talk) 21:10, 22 April 2010 (UTC)

Baldwin's rules

I have created and uploaded some images for the Baldwin's rules: http://commons.wikimedia.org/wiki/File:Baldwin_rules_enolates.png, http://commons.wikimedia.org/wiki/File:Cyclization_preferred_ts_geometries.gif, http://commons.wikimedia.org/wiki/File:Preussin_synthesis_key_step.gif

You might want to use it to expand the existing page on the Baldwin's rules (currently I am too busy working on the Russian version of this article). Жора Ковский (talk) 06:44, 16 May 2010 (UTC)

• Thanks! I have modified the page accordingly. V8rik (talk) 19:43, 19 May 2010 (UTC)

File: MetathesisCalderon1967.svg

The structure on the right-hand side of MetathesisCalderon1967.svg has one too many carbons —Preceding unsigned comment added by Seuraza (talk • contribs) 00:56, 24 May 2010 (UTC)

• Thanks for spotting the error, image has been modified V8rik (talk) 21:01, 24 May 2010 (UTC)

Thanks for catching that error in "Stereochemistry of Ketonization of Enols and Enolates; Kinetic Protonation"

To: V8rik From: Howard Z

I really appreciate your catching that error in the article on "Stereochemistry of Ketonization of Enols and Enolates; Kinetic Protonation".

The captions (giving the reaction conditions) for the enol acetate and the alpha-bromoketone had been reversed in error.

I've fixed that now. It would not hurt to check.

It is good to know that someone is noticing the articles I've worked on. For kinetic protonation it seems that only half the people making us of the phenomenon know about its origin. AND, it was "Rediscovered" twice - Takano in Japan and an old friend in Germany, Siegrief Hünig in Würzburg. In the last publication there is mention of the rediscoveries.

Best wishes, Howard Z

Howard E. Zimmerman 20:18, 30 May 2010 (UTC) —Preceding unsigned comment added by Hezimmerman (talk • contribs)

• Thanks Hezimmerman, glad to be able to help. V8rik (talk) 21:33, 31 May 2010 (UTC)

You are now a Reviewer

Hello. Your account has been granted the "reviewer" userright, allowing you to review other users' edits on certain flagged pages. Pending changes, also known as flagged protection, will be commencing a two-month trial at approximately 23:00, 2010 June 15 (UTC).

Reviewers can review edits made by users who are not autoconfirmed to articles placed under flagged protection. Flagged protection is applied to only a small number of articles, similarly to how semi-protection is applied but in a more controlled way for the trial.

When reviewing, edits should be accepted if they are not obvious vandalism or BLP violations, and not clearly problematic in light of the reason given for protection (see Wikipedia:Reviewing process). More detailed documentation and guidelines can be found here.

If you do not want this userright, you may ask any administrator to remove it for you at any time. Courcelles (talk) 20:19, 15 June 2010 (UTC)

DYK for tert-Butanesulfinamide

— Rlevse • Talk • 18:02, 16 June 2010 (UTC)

Passerini reaction

Hi.

This scheme illustrating the Passerini reaction contains a mistake: http://en.wikipedia.org/wiki/File:PasseriniReaction.svg

A cyanide is drawn instead of an isocyanide.

-- Alex kovsky (talk) 20:40, 9 July 2010 (UTC)

• Thanks for the notification, the image has been replaced. V8rik (talk) 21:07, 9 July 2010 (UTC)

File:Zipper mode.gif listed for deletion

A file that you uploaded or altered, File:Zipper mode.gif, has been listed at Wikipedia:Files for deletion. Please see the discussion to see why this is (you may have to search for the title of the image to find its entry), if you are interested in it not being deleted. Thank you. --Master Uegly (talk) 19:20, 14 July 2010 (UTC) —Preceding unsigned comment added by 139.18.189.107 (talk)

The Woodward-Hoffmann (4q+2)s & (4r)s Rule

Good Afternoon V8rik,

I noted your comment and you are correct; the Present Pericyclic W-H article doesn't mention the (4q+2)s & (4r)s rule. It was only the comment by Koala Paw who wanted that inserted a "the most important" item.

That (4q+2)s & (4r)s Rule appeared in the 1970 booklet by Wood-Ward and Hoffmann "conservation of Orbital Symmetry". But whoever wrote the Wikipedia article had not included that item that Koala Paw wanted.

Thus, if someone was going to insert that (4q+2)s & (4r)s rule, I wanted that person to be aware of its being a direct consequence of my Möbius-Hückel stuff. Thus, each (4r)s component has one +/- node with a an odd-number of these one has a Möbius cycle with a multiple of four electrons. As long as it is not inserted, then my comments are not relevant.

There is another, unrelated point, namely that the 1961 Zimmerman-Zweig article was the first to present oragnic correlation diagrams and the conseequence of occupied bonding electrons going antibonding in a reaction. As a former student of Woodward and his friend, I have to believe that he was unaware of that earlier work. But it is relevant to the entire matter. V4rik, I think you and I have a lot in common, just judging by comments you have made.

Best wishes,

Howard Z I've put in Hez for my signature, not wanting to advertize my name everytime I write. Hez (talk) 21:17, 17 July 2010 (UTC)

• Hi Hez, Thanks for the explanation, I had not realized your comment was really a comment to the remarks made by user Koala Paw. V8rik (talk) 20:37, 20 July 2010 (UTC)

More on The Woodward-Hoffmann (4q+2)s & (4r)s Rule

To: V8rik From: Howard Z

V8rik,

I may have read your point too hastily and responded only to part.

In tht 1965 Woodward-Hoffmann article there is discussion of 4q and and 4q+2 but in a different context than in their 1970 publication. In the 1965 article they have used these to describe the number of bonding and antibonding levels (or MO's). I haven't found a connection there to the number of molecular components of a basis set. I hope I'm not misunderstanding anything.

V8rik, I'm assuming that this is the best place to put in stuff meant to reach you.

Best wishes,

Howard Z Hez (talk) 19:28, 18 July 2010 (UTC)

• Yes the context is different~, that is important to understand. BTW you can always reach me on this page but in general the talk page of the page in question is always a good place to have discussions. V8rik (talk) 20:41, 20 July 2010 (UTC)

File:Schiffbase.png

Your picture has been nominated for deletion on Commons: commons:Commons:Deletion requests/File:Schiffbase.png. Trycatch (talk) 07:56, 22 August 2010 (UTC)

File source problem with File:TMP synthesis.gif

Thank you for uploading File:TMP synthesis.gif. I noticed that the file's description page currently doesn't specify who created the content, so the copyright status is unclear. If you did not create this file yourself, you will need to specify the owner of the copyright. If you obtained it from a website, please add a link to the website from which it was taken, together with a brief restatement of that website's terms of use of its content. However, if the copyright holder is a party unaffiliated from the website's publisher, that copyright should also be acknowledged.

If you have uploaded other files, consider verifying that you have specified sources for those files as well. You can find a list of files you have created in your upload log. Unsourced and untagged images may be deleted one week after they have been tagged per Wikipedia's criteria for speedy deletion, F4. If the image is copyrighted and non-free, the image will be deleted 48 hours after 09:13, 30 August 2010 (UTC) per speedy deletion criterion F7. If you have any questions or are in need of assistance please ask them at the Media copyright questions page. Thank you. Sfan00 IMG (talk) 09:13, 30 August 2010 (UTC)

Ritchie equation diazonium ions

I have re-uploaded the image [1] to Wikipedia Commons - [2] - to be able to use it on other Wikies. However, I would be grateful for an explanation how it can done simplier (i.e. by clicking one button). --kovsky (talk) 09:16, 2 September 2010 (UTC)

File:Heck silica.gif missing description details

Dear uploader: The media file you uploaded as File:Heck silica.gif is missing a description and/or other details on its image description page. If possible, please add this information. This will help other editors to make better use of the image, and it will be more informative for readers.

If the information is not provided, the image may eventually be proposed for deletion, a situation which is not desirable, and which can easily be avoided.

If you have any questions please see Help:Image page. Thank you. Sfan00 IMG (talk) 11:37, 13 September 2010 (UTC)

Hock rgmt?

In my wanderings on Ullmann, I ran into this reaction, which we dont have: "Hock rearrangement". I think is the path for converting hydroperoxides (such as cumene hydroperoxide) into phenols. I mention this puzzle to you as one of our experts on name reactions. Cheers, --Smokefoot (talk) 15:53, 23 October 2010 (UTC)

• Mystery solved: according to the German Cumene process page The Hock rearrangement is step three. They even have a bio! V8rik (talk) 23:05, 23 October 2010 (UTC)

Organosilver chemistry

Hey there V8rik

I removed a sentence from organosilver chemistry:

A notable compound is pentafluorophenyl silver obtained from the aryllithium compound and silver trifluoroacetate:

C6H5Li + F3(CO)OAg → C6H6Ag + F3(CO)OAg

as colorless crystals. It slowly decomposes in presence of oxygen with formation of the aryl radical and is sensitive to hydrolysis. The compound is stable up to 270°C.

I just checked the history and found that you were responsible for the majority of the content. The text and the equation doesn't seem to match. Would you be able to check it, and re-add it with a ref? Thanks. --Rifleman 82 (talk) 22:28, 30 October 2010 (UTC)

• This question could have been handled by Talk:Organosilver_chemistry, adding a tag like would have been an option. I guess we will never know how to synthesise it as the content is now gone. V8rik (talk) 21:38, 31 October 2010 (UTC)

• • I removed that chunk because the equation doesn't make sense. Instead of leaving questionable content on the page, I took it out and brought it to your attention, since it was in the first revision which you wrote [3]. It's not gone, it still exists in the history, which is accessible by anyone at any time. Do you recall which references you used to write the article? That would be most convenient. If you can't or don't want to, I suppose I or anyone else can rewrite this content from scratch. --Rifleman 82 (talk) 21:58, 31 October 2010 (UTC)

• • • The primary sources were references 1 and 2 and yes, anyone can write a organosilver silver page from scratch V8rik (talk) 22:45, 31 October 2010 (UTC)

Xylenol

It surprises me that you would think such a detailed reaction mechanism is all that relevant to xylenol. (I'm assuming that's your reasoning for the revert, in the absence of any edit summary...) It's not a big deal to me, but reverting my other minor copyediting to the article is at the very least counter productive. -- Ed (Edgar181) 18:26, 19 November 2010 (UTC)

• Hi Edgar, yes I should have seen the other edit, my apologies. V8rik (talk) 18:38, 19 November 2010 (UTC)

OK, no problem. Would you object to relocating that content to 2,6-Xylenol, since it is specific to that isomer? -- Ed (Edgar181) 18:41, 19 November 2010 (UTC)

the only way to make it up to you is to do the relocating myself, expect results within 10 minutes V8rik (talk) 18:44, 19 November 2010 (UTC)

Done! V8rik (talk) 18:48, 19 November 2010 (UTC)

Great. Thank you. -- Ed (Edgar181) 18:52, 19 November 2010 (UTC)

Hydroxide

I need help on the use of hydroxide in organic chemistry. I don't have good sources to hand for citations. My draft is at User:Petergans/sandbox. Please have a look at it and comment if you can. Petergans (talk) 14:01, 8 December 2010 (UTC)

• Hi Petergans, I can try to write a segment on use in orgchem, will try to get sources over the next week V8rik (talk) 22:59, 8 December 2010 (UTC)
  • I still owed you some content on the hydroxide anion in orgchem and I noticed that you have updated the hydroxide article. It is difficult to find specific info on this topic but i feel that the additions I have made are usefull. Hope it helps. By the way thanks for your intervention on the zwitterion page V8rik (talk) 21:43, 1 January 2011 (UTC)

Got it

Okay, thanks. --Smokefoot (talk) 19:47, 11 December 2010 (UTC)

Hammett law article

I got to it via piece on University and school student projects!! From that misunderstanding I asked if I could contribute a comment and question. Now I see my error in that respect, should I put them here or there?Michael P. Barnett (talk) 15:10, 12 December 2010 (UTC)

• See my reply : Hammett_equation#Outsider.27s_comment_and_question V8rik (talk) 17:25, 13 December 2010 (UTC)

Zwitterion

Hi V8rik, could you help me? talk:Zwitterion They say, they need an expert but they do not believe what I say. Maybe you are more credible, because I am a very new user. If you do not have enough time for this, I can also understand it. Have a nice Christmas. Regards --Azaline Gomberg (talk) 18:13, 21 December 2010 (UTC)

• Hi Azaline, I will try V8rik (talk) 21:22, 21 December 2010 (UTC)

MakaiyamaAldolReaction.svg

The image posted has an error. The formula for trimethylchlorosilane is incorrect and should read (CH3)3SiCl (additional brackets and '3'). I do not use BKchem and cannot edit the picture - perhaps you could correct this. Both occurrences of the formula are incorrect. http://en.wikipedia.org/wiki/File:MakaiyamaAldolReaction.svg Chemicadian (talk) 10:07, 24 December 2010 (UTC)

• Thanks for bringing it to my attention, the replacement is already installed V8rik (talk) 19:56, 27 December 2010 (UTC)

File source problem with File:AmbiguineSynthesisBagan2007.svg

Thank you for uploading File:AmbiguineSynthesisBagan2007.svg. I noticed that the file's description page currently doesn't specify who created the content, so the copyright status is unclear. If you did not create this file yourself, you will need to specify the owner of the copyright. If you obtained it from a website, please add a link to the website from which it was taken, together with a brief restatement of that website's terms of use of its content. However, if the copyright holder is a party unaffiliated from the website's publisher, that copyright should also be acknowledged.

If you have uploaded other files, consider verifying that you have specified sources for those files as well. You can find a list of files you have created in your upload log. Unsourced and untagged images may be deleted one week after they have been tagged per Wikipedia's criteria for speedy deletion, F4. If the image is copyrighted and non-free, the image will be deleted 48 hours after 16:14, 28 December 2010 (UTC) per speedy deletion criterion F7. If you have any questions or are in need of assistance please ask them at the Media copyright questions page. Thank you. Saibo (Δ) 16:14, 28 December 2010 (UTC)

Same for File:HapalindoleUsynthesisMuratake1990.svg please.Saibo (Δ) 16:14, 28 December 2010 (UTC)

Hi Saibo,

(my German is lousy)

You (or your bot) have left me a note regarding AmbiguineSynthesisBagan2007.svg, it is up for deletion? I have created hundreds of images (self-created) for wikipedia and I have always followed Wikipedia guidelines. Something must have gone wrong V8rik@en.wikipedia.org

Hi V8rik, thank you for your respone. It was me asking for a source. Nothing will be deleted if the source of the file is known! Sorry for "shocking" you.

If you created them yourself all is okay. To get it best, could you use {{own}} after "source=" if you created them by yourself? A simple "self drawn" in the description text somewhere is also sufficient.

I was asking for a source since I would like to transfer both files to Commons so we at de.wikipedia can use your drawings! Files moved to Commons should be checked for being correctly licensed - and if the source is missing it is not clear that you have drawn them yourself.

It would be best if you could upload future drawings directly to Commons. If you have any problems I would be happy to help you.

Thank you very much for your help! :-) Please just answer here. I watch your page. Cheers --Saibo (Δ) 19:41, 28 December 2010 (UTC)

Structural isomer

Please visit talk-page. DMacks (talk) 18:55, 31 December 2010 (UTC)

MO diagram pics

Hello V8rik,

I've noticed you've contributed to the MO diagram article in the past, including making pictures of MO diagrams and a description of the MO diagram of water, but not a picture of the water diagram. Are you working or planning to work on an MO diagram for water in the future? ... or for HF, CO, NH₃, CH₄, formaldehyde (H₂CO), or benzene? If so, I think I will wait for the ones you plan to finish. If not, maybe some day I may have a go at some of them. It will take time though, I think. H Padleckas (talk) 20:55, 15 January 2011 (UTC)

• Hi H Padleckas, I have no plans creating pics for this article. The simple reasons are I do not have access to proper software and I lack the required graphical skills. I also have no plans for extending the article with new molecules. If you are willing to expand the article and create pics it is greatly appreciated, many advance thanks V8rik (talk) 19:25, 16 January 2011 (UTC)

Thanks for replying. H Padleckas (talk) 04:18, 17 January 2011 (UTC)

R2CuLi + R'X coupling

The Substitution reactions subsection in Organocopper compound recently said (Certain items I bolded here):

"Substitution reactions of cuprates R₂CuLi to alkyl halides R'-X gives the alkylcopper compound R'-Cu, the coupling product R-R and the lithium halide. The reaction mechanism is based on nucleophilic attack, namely oxidative addition of the alkyl halide to Cu(I) elevating it to a planar Cu(III) intermediate followed by reductive elimination. The nucleophilic attack is the rate-determining step. In the case for substitution of iodide, single electron transfer mechanism is proposed (see figure).

Many electrophiles will work. The approximate order of reactivity, beginning with the most reactive, is as follows: acid chlorides>aldehydes > tosylates ~ epoxides > iodides > bromides > chlorides > ketones > esters > nitriles >> alkenes"

It seems to me R'-Cu and R-R in the first sentence is not consistent with your reaction picture. Therefore, I changed the opening sentence to read:

"Substitution reactions of cuprates R₂CuLi to alkyl halides R'-X gives the alkylcopper compound R-Cu, the coupling product R-R', and the lithium halide Li-X."

for consistency with your picture (Corrections bolded here but not in article). If in fact the initial sentence was correct before, then you may want to reverse my edit and change your picture, or tell me to make these changes. If your picture is correct, perhaps it should also be added to the Gilman reagent article, perhaps in a simplified form.

Also perhaps this reaction should be added to the list in Coupling reaction. H Padleckas (talk) 20:28, 17 January 2011 (UTC)

• Hi H Padleckas, your analysis is correct, the coupling product is R-R' . Your edit has set it straight V8rik (talk) 22:24, 18 January 2011 (UTC)

Polycyclic aromatic hydrocarbons

Hi V8rik... I noticed that you uploaded the image File:TheClarRule.png. Structure 4C is missing one double bond along the common bond fusing rings 2 and 3, I think. If you still have the source file, maybe you could correct the structure? EdChem (talk) 11:23, 20 January 2011 (UTC)

• Done! V8rik (talk) 20:35, 8 March 2011 (UTC)

Mistake in File:Stannabenzene.png

There are some chemical typos in your diagram--see concerns noted on the file description page. You appear not to have a commons account? Let me know if you need help getting images transferred from .en. DMacks (talk) 11:55, 20 January 2011 (UTC)

• Hi DMacks, thanks for the notice, the image has been replaced. I do have a commons account, not all of my images have been transfered yet though V8rik (talk) 23:15, 21 January 2011 (UTC)

Thanks for the fix! DMacks (talk) 23:17, 21 January 2011 (UTC)

Zwitterionic quinonoid.gif

Hi there. The charges in the third species of this gif (the zwitterion) are in the wrong place. They are delocalised, so should be in the centre of the two delocalised systems, not at the sides. Cheers, Chris (talk) 19:45, 2 March 2011 (UTC)

• Taken care of V8rik (talk) 21:51, 7 March 2011 (UTC)

Thanks! Chris (talk) 10:22, 8 March 2011 (UTC)