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A ^(15)N nuclear magnetic resonance study of the base-catalyzed NH_2 exchange reactions of acetamide and thioacetamide

Nee, Michael and Chun, Yu and Squillacote, Michael E. and Roberts, John D. (1982) A ^(15)N nuclear magnetic resonance study of the base-catalyzed NH_2 exchange reactions of acetamide and thioacetamide. Organic Magnetic Resonance, 18 (3). pp. 125-127. ISSN 0030-4921. http://resolver.caltech.edu/CaltechAUTHORS:20151005-120248398

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Abstract

The base-catalyzed -NH_2 exchange reactions of acetamide and thioacetamide were studied by ^(15)N nuclear magnetic resonance spectroscopy by the use of line-shape analysis. The ^(15)N NMR spectra of these primary amides at intermediate exchange rates were broad doublets, which indicated that the two amide protons were exchanging at different rates. The line-shape analysis indicated that the ratio of exchange rates was 6 ± 1 for acetamide and 3 ± 1 for thioacetamide.


Item Type:Article
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http://dx.doi.org/10.1002/mrc.1270180302DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/mrc.1270180302/abstractPublisherArticle
Additional Information:© 1982 Heyden & Son Ltd. Received 6 October 1980; accepted (revised) 21 September 1981. This work was supported by the National Science Foundation, and by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences. The authors are indebted to Professor Charles Perrin for his suggestion that the ^(15)N spectra could be used to determine these rate ratios. We are also grateful to Professor F. A. L. Anet for help with the use of his site-exchange program.
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and CreUin Laboratories of Chemistry6500
Record Number:CaltechAUTHORS:20151005-120248398
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151005-120248398
Official Citation:Nee, M., Chun, Y., Squillacote, M. E. and Roberts, J. D. (1982), A 15N nuclear magnetic resonance study of the base-catalyzed NH2 exchange reactions of acetamide and thioacetamide. Org. Magn. Reson., 18: 125–127. doi: 10.1002/mrc.1270180302
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ID Code:60764
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:05 Oct 2015 22:20
Last Modified:05 Oct 2015 22:20

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