Schuster, Ingeborg I. and Doss, Senot H. and Roberts, John D. (1978) Natural-abundance nitrogen-15 nuclear magnetic resonance spectroscopy. Electronic effects in benzenesulfonamides. Journal of Organic Chemistry, 43 (25). pp. 4693-4696. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20151007-093104006
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Abstract
The ^(15)N chemical shifts of a number of benzenesulfonamides with different substituents at nitrogen have been measured in dimethyl sulfoxide solution and compared to those of similarly substituted benzenamines and ethanamides. The relative extent of phenyl-sulfur and nitrogen-sulfur p_π-d_π orbital overlap is discussed. Substitution of C_6H_5SO_2 for one benzyl group of N,N-dibenzylethanamide results in considerable lowering of the free energy of activation of the N-CO bond rotation.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1978 American Chemical Society. Received May 24, 1978. Supported by the National Science Foundation and by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences. | |||||||||
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| Issue or Number: | 25 | |||||||||
| Record Number: | CaltechAUTHORS:20151007-093104006 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151007-093104006 | |||||||||
| Official Citation: | Natural-abundance nitrogen-15 nuclear magnetic resonance spectroscopy. Electronic effects in benzenesulfonamides Ingeborg I. Schuster, Senot H. Doss, and John D. Roberts The Journal of Organic Chemistry 1978 43 (25), 4693-4696 DOI: 10.1021/jo00419a002 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 60865 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 07 Oct 2015 22:41 | |||||||||
| Last Modified: | 03 Oct 2019 09:01 |
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