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Electronic substituent effects on nitrogen-15 shieldings of N-(arylmethylidene)cyclohexanamine hydrofluoroacetates

Botto, Robert E. and Roberts, John D. (1979) Electronic substituent effects on nitrogen-15 shieldings of N-(arylmethylidene)cyclohexanamine hydrofluoroacetates. Journal of Organic Chemistry, 44 (1). pp. 140-141. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20151007-093102782

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Abstract

An earlier ^(15)NMR study of several series of para-substituted N-(arylmethylidene)amines 1 and 2 has shown that the nitrogen shifts are sensitive to the electronic influence of the ring substituents (X), as reflected by the Hammett o substituent parameters. Reasonable linear correlations could also be obtained for the nitrogen shifts of compounds in each series and the β-carbon shieldings of 4-substituted ethenylbenzenes 3, with the changes in the ^(15)N shifts generally being about twice that of the ^(13)C shifts with respect to the substituent effects. To determine whether the greater sensitivity of the nitrogen shifts arises predominantly from a substituent induced perturbation of the nitrogen unshared pair of electrons, we have measured ^(15)N chemical shifts of a series of para-substituted N-(arylmethylidene)cyclohexanamine hydrotrifluoroacetates.


Item Type:Article
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http://dx.doi.org/10.1021/jo01315a032DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo01315a032PublisherArticle
Additional Information:© 1979 American Chemical Society. Received August 1, 1978. Supported by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences, and by the National Science Foundation.
Funders:
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry5846
Record Number:CaltechAUTHORS:20151007-093102782
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151007-093102782
Official Citation:Electronic substituent effects on nitrogen-15 shieldings of N-(arylmethylidene)cyclohexanamine hydrofluoroacetates Robert E. Botto and John D. Roberts The Journal of Organic Chemistry 1979 44 (1), 140-141 DOI: 10.1021/jo01315a032
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60861
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 22:45
Last Modified:07 Oct 2015 22:45

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