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Natural-abundance nitrogen-15 nuclear magnetic resonance spectroscopy. Electronic effects in benzenesulfonamides

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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo00419a002DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00419a002PublisherArticle
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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
U.S. Public Health Service (USPHS)GM-11072
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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