Yavari, Issa and Roberts, John D. (1978) Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. A Simple Procedure for Determination of the Rates of N-H Proton Exchange of cis- and trans-1-Aza-2-cyclononanone. Journal of the American Chemical Society, 100 (16). pp. 5217-5218. ISSN 0002-7863. doi:10.1021/ja00484a057. https://resolver.caltech.edu/CaltechAUTHORS:20151007-093104568
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Abstract
Several investigations have been made to determine the relative rates of N-H proton exchange in cis and trans isomers of peptide bonds. N-Methylacetamide and medium-ring lactams have been traditional models for the cis and trans isomers, respectively. Klotz and Feidelseit have reported that base-catalyzed N-H proton exchange of 1-aza-2-cyclopentanone is much faster than that of N-methylacetamide. However, Chen and Swenson4 subsequently found that amide protons of 1-aza-2-cycloheptanone exchange more slowly than those of N-methylacetamide in deuterium oxide solution. The nine-membered ring lactam, 1-aza-2-cyclononanone (l), is well established, to exist in several solvents as a nearly 1:l mixture of the cis and trans isomers and, as such, is well suited as a model for both the cis- and trans-amide bonds. We present here the results of a ^(15)N NMR study of base-catalyzed N-H proton-exchange reactions of 1 at the natural-abundance level of the isotope in dimethyl sulfoxide and in 80% aqueous ethanol.
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Additional Information: | © 1978 American Chemical Society. Received March 31, 1978. Supported by the National Science Foundation and by the Public Health Service, Research Grant No. GM-11072, from the Division of General Medical Sciences. | |||||||||
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Issue or Number: | 16 | |||||||||
DOI: | 10.1021/ja00484a057 | |||||||||
Record Number: | CaltechAUTHORS:20151007-093104568 | |||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151007-093104568 | |||||||||
Official Citation: | Nitrogen-15 nuclear magnetic resonance spectroscopy. A simple procedure for determination of the rates of nitrogen-hydrogen proton exchange of cis- and trans-1-aza-2-cyclononanone Issa Yavari and John D. Roberts Journal of the American Chemical Society 1978 100 (16), 5217-5218 DOI: 10.1021/ja00484a057 | |||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
ID Code: | 60867 | |||||||||
Collection: | CaltechAUTHORS | |||||||||
Deposited By: | Ruth Sustaita | |||||||||
Deposited On: | 07 Oct 2015 22:32 | |||||||||
Last Modified: | 10 Nov 2021 22:40 |
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