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. doi:10.1021/jo01315a032. https://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.
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| 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. | |||||||||
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| Issue or Number: | 1 | |||||||||
| DOI: | 10.1021/jo01315a032 | |||||||||
| Record Number: | CaltechAUTHORS:20151007-093102782 | |||||||||
| Persistent URL: | https://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: | INVALID USER | |||||||||
| Deposited On: | 07 Oct 2015 22:45 | |||||||||
| Last Modified: | 10 Nov 2021 22:40 |
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