Published March 1982
| public
Journal Article
A ^(15)N nuclear magnetic resonance study of the base-catalyzed NH_2 exchange reactions of acetamide and thioacetamide
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.
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.Additional details
- Eprint ID
- 60764
- DOI
- 10.1002/mrc.1270180302
- Resolver ID
- CaltechAUTHORS:20151005-120248398
- NSF
- GM-11072
- U.S. Public Health Service (USPHS)
- Created
-
2015-10-05Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and CreUin Laboratories of Chemistry
- Other Numbering System Identifier
- 6500