Published February 1982 | public
Journal Article

Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. N—H Proton Exchange Reactions of Urea, Thiourea, Acetamide and Thioacetamide

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Abstract

Measurements are reported of NH exchange rates of urea, thiourea, acetamide and thioacetamide, using line-shape analysis with natural-abundance ^(15)N NMR spectra. Base-catalyzed NH-proton exchange of thiourea is 30–40 times faster than for urea, while the corresponding acid-catalyzed exchange is 150 times slower. The base-catalyzed proton exchange for thioacetamide is about 1000 times faster than that of acetamide at 25°C, while the corresponding acid-catalyzed exchange is some 260 times slower.

Additional Information

© 1982 Heyden & Son Ltd. Received 22 January 1981 ; accepted 31 August 1981. Supported by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences, and by the National Science Foundation.

Additional details

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August 19, 2023
Modified:
October 24, 2023