Talk:2-Norbornyl cation

Major Additions, December 2013
Hello. I will be adding a lot more sections to this article in the next few days: I have done a lot of research and would like to make this page even better. I am happy to take any comments/suggestions on how to make this page even better! — Preceding unsigned comment added by Jcal730 (talk • contribs) 07:35, 6 December 2013 (UTC)


 * A non-classical ion is not equivalent to the 2-norbornyl cation, please revert the move, then discuss V8rik (talk) 18:06, 6 December 2013 (UTC)
 * The old page did not discuss non-classical ions except for a 6-line section at the end about ethynium, ethenium, and ethanium. I have included this section under section 1.3 in the current article, making reference to these other ions in the same way as the previous version of the article. In addition, the 2-norbornyl cation is the prototypical non-classical ion, and thus a more in-depth explanation will be quite informative not only for the rich history surrounding non-classical ion research but also for explaining key concepts in non-classical ions. If you would still like me to revert the move given this argument, I can do so. However, I will then take all of the research that I have done on the 2-norbornyl cation and add it to this page instead. As I will be discussing all of the other topics covered in the previous version of the article in the other sections I will be uploading, I think it may be clunky to keep the old article after my other additions are made. Note: The old article was very helpful in introducing me to the debate and starting my research, and I indeed want to preserve the information contained in it. Jcal730 (talk) 18:29, 6 December 2013 (UTC)

Norbornyl brosylate solvolysis.png
I think that the figure on norbornyl brosylate solvolysis is very informative. Unfortunately the paper by Winstein/Trifan cited (doi:10.1021/ja01176a536) does not actually investigate endo-norbornyl p-bromo-benzenesulfonate but simply states that investigations are underway. They instead use the endo-tosylate. Would you be able to either change the figure to account for this or provide the citation for a later paper in which the endo-brosylate is discussed?

Would you be able to change the carbon in the acetate to more accurately depict its geometry. It is typically not drawn in a linear fashion.

Finally, could you add the racemic indicator to all three main structures in this figure?

If you do not have time to make these edits, I'd be happy to do them if you send me the source code for the figure.

I also find the second figure in the original article quite informative. Jcal730 (talk) 19:35, 6 December 2013 (UTC)


 * in the original revision the citation was the 1949 Winstein work @ http://dx.doi,org/10.1021/ja01176a536, I lack the time to redo any of the images so please go ahead V8rik (talk) 18:17, 9 December 2013 (UTC)
 * I tried to upload the new file I made but it didn't work- it is now on the Wikimedia Commons page though as an earlier version (I've reverted it to the original.) Do you know why I wasn't able to get it to switch over to the new file? Jcal730 (talk) 21:10, 13 December 2013 (UTC)

Needs citation to go back in article
Further evidence for the non-classical model was obtained by tracer studies in which two carbon atoms in the norbornyl skeleton were replaced by the radioactive carbon 14 isotopes (Scheme 4). The primary solvolyis reaction product was derivatized by reduction with lithium aluminium hydride and oxidation with sodium permanganate to the dicarboxylic acid followed by a Curtius rearrangement expelling carbon dioxide. When the acetyl anion is indeed able to attack both C1 and C2 positions of the symmetrical norbornyl cation 2 then 50% of the generated CO2 will contain 14C. The experimental value in this experiment was 40% and in order to account for the presence of 14C in other positions (a scrambling process) the nortricyclonium cation was postulated which is basically a face-capped norbornyl cation allowing hydride shifts.

Jcal730 (talk) 16:22, 9 December 2013 (UTC)


 * the citation got lost some time ago due to lousy editing, you could check older revisions, like this one V8rik (talk) 17:58, 9 December 2013 (UTC)
 * I would have to recheck the citations: the isotope study possibly is http://dx.doi.org/10.1021/ja01647a001. The other citations already mentioned in the earlier versin are http://dx.doi.org/10.1021/ja01154a555 and http://dx.doi.org/10.1021/ja01078a056 V8rik (talk) 18:03, 9 December 2013 (UTC)
 * Great, I'll put it back in later today along with some more new info. Thanks! Jcal730 (talk) 21:10, 13 December 2013 (UTC)