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^(13)C, ^1H, and ^2H NMR Observation of Trideuterated Cyclopropylmethyl-Cyclobutyl Carbocation: A Configurationally Stable Species

Brittain, William J. and Squillacoate, Michael E. and Roberts, John D. (1984) ^(13)C, ^1H, and ^2H NMR Observation of Trideuterated Cyclopropylmethyl-Cyclobutyl Carbocation: A Configurationally Stable Species. Journal of the American Chemical Society, 106 (23). pp. 7280-7282. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151002-123937774

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Abstract

With the increasing power and sophistication of experimental and theoretical methods for assigning chemical structures, it seems almost incredible that the structure of any reasonably stable organic entity with a small number of carbons could remain enigmatic for very long. Nonetheless, this is true of C_4H_7^+-one of the first "nonclassical" cations to be discovered, which has some of the characteristics expected for a very rapidly equilibrating mixture of classical cyclopropylmethyl, cyclobutyl, and 3-butenyl cations and yet other characteristics which wholly belie any description that implies conventional charge distributions or geometries derived from structural representations using solid lines representing two-electron bonds.


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http://dx.doi.org/10.1021/ja00335a089DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00335a089PublisherArticle
Alternate Title:Carbon-13, proton, and deuteron NMR observation of trideuterated cyclopropylmethyl-cyclobutyl carbocation, a configurationally stable species
Additional Information:© 1984 American Chemical Society. Received April 18, 1984. Revised Manuscript Received September 8, 1984. We are pleased to acknowledge use of the Southern California Regional NMR Center facilities (Bruker WM-500 spectrometer) supported by the National Science Foundation, Grant CHE79- 16324, and helpful discussions with Professor Martin Saunders of Yale University.
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NSFCHE79-16324
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Caltech Gates and Crellin Laboratories of Chemistry7016
Record Number:CaltechAUTHORS:20151002-123937774
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151002-123937774
Official Citation:Carbon-13, proton, and deuteron NMR observation of trideuterated cyclopropylmethyl-cyclobutyl carbocation, a configurationally stable species William J. Brittain, Michael E. Squillacoate, and John D. Roberts Journal of the American Chemical Society 1984 106 (23), 7280-7282 DOI: 10.1021/ja00335a089
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60719
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:05 Oct 2015 14:33
Last Modified:05 Oct 2015 14:33

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