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Published 1978 | public
Journal Article

^(15)N Nuclear Magnetic Resonance Spectroscopic Investigation of Differential Rates of Base-Catalyzed N-H Proton-Exchange Reactions of 1-aza-2-Cycloheptanone and 1-aza-2-Cycloheptanethione

Abstract

Natural-abundance proton-coupled ^(15)N NMR spectra of an equimolar solution of the title compounds in dimethyl sulfoxide, to which was added aqueous sodium hydroxide, show that N-H proton exchange of the thiolactam is about 1500 times faster than that of the lactam at 25°C. This rate difference is suggested to arise from a greater contribution of the polar resonance structure for the thiolactam.

Additional Information

© 1978 Pergamon Press Ltd. Received in USA 18 April 1978; received in UK for publication 16 May 1978. Supported by the National Science Foundation, and by the Public Health Service, Research Grant No. GM-11073 from the Division of General Medical Sciences.

Additional details

Created:
August 19, 2023
Modified:
October 25, 2023