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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

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.

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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.
Funding AgencyGrant Number
U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry5757
Issue or Number:16
Record Number:CaltechAUTHORS:20151007-093104568
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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
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 22:32
Last Modified:10 Nov 2021 22:40

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