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Published July 1, 1978 | public
Journal Article

Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. Differential Rates of N-H Proton-Transfer Reactions in Phenylhydrazine

Abstract

High-resolution proton-coupled ^(15)N NMR spectra of neat phenylhydrazine (1) have been studied at the natural abundance level over the temperature range of 20-70 ºC. Proton transfer from the -NH_2 group was found to be about two orders of magnitude faster than that from the -NH- group. The ^(15)N chemical shifts of 1 in a variety of basic, neutral, and acidic solvents show that influences of the medium are different for the two types of nitrogens in 1. Proton-coupled ^(15)N spectra of 1 in various solvents confirm the results of the variable-temperature studies. The differential rates of the proton-transfer reactions of 1 can be ascribed to two different bimolecular exchange mechanisms.

Additional Information

© 1978 American Chemical Society. Received December 12, 1977. July 19, 1978. Supported by the National Science Foundation, and by the Public Health Service, Research Grant GM-11073 from the Division of General Medical Sciences.

Additional details

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