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

Chun, Yu and Yavari, Issa and Roberts, John D. (1982) Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. N—H Proton Exchange Reactions of Urea, Thiourea, Acetamide and Thioacetamide. Organic Magnetic Resonance, 18 (2). pp. 74-76. ISSN 0030-4921. http://resolver.caltech.edu/CaltechAUTHORS:20151005-120248654

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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.


Item Type:Article
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http://dx.doi.org/10.1002/mrc.1270180205DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/mrc.1270180205/abstractPublisherArticle
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.
Funders:
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and CreUjn Laboratories of Chemistr6378
Record Number:CaltechAUTHORS:20151005-120248654
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151005-120248654
Official Citation:Chun, Y., Yavari, I. and Roberts, J. D. (1982), Nitrogen-15 nuclear magnetic resonance spectroscopy. N[BOND]H proton exchange reactions of urea, thiourea, acetamide and thioacetamide. Org. Magn. Reson., 18: 74–76. doi: 10.1002/mrc.1270180205
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ID Code:60765
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:05 Oct 2015 22:28
Last Modified:05 Oct 2015 22:28

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