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Wei-Hsien Wang, Pai-Hui Cheng, Hsing-Ching Hsieh, Mechanistic Study of Acid-Catalyzed Proton Exchange in Thioamide and Thiolactams, Bulletin of the Chemical Society of Japan, Volume 66, Issue 7, July 1993, Pages 2073–2076, https://doi.org/10.1246/bcsj.66.2073
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Abstract
The kinetics of acid-catalyzed proton exchange in a series of thiolactams (5- to 7-membered ring) and N-methylthioacetamide were studied. Kinetic data were observed by NMR line-broadening and computer simulation methods. The second-order rate constants of all the thiolactams and N-methylthioacetamide are within the same order of magnitude. It is concluded that the imidic acid mechanism is dominant in thiolactams and N-methylthioacetamide.
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© 1993 The Chemical Society of Japan
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