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Published December 1, 1978 | public
Journal Article

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

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.

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.

Additional details

Created:
August 19, 2023
Modified:
October 24, 2023