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Nitrogen-15 Magnetic Resonance Spectroscopy. Natural-Abundance Spectra of Secondary Amides

Westerman, Philip W. and Roberts, John D. (1978) Nitrogen-15 Magnetic Resonance Spectroscopy. Natural-Abundance Spectra of Secondary Amides. Journal of Organic Chemistry, 43 (6). pp. 1177-1179. ISSN 0022-3263. doi:10.1021/jo00400a033.

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The ^(15)N chemical shifts of 17 N-alkyl- and N-arylethanamides have been determined at the natural-abundance level of ^(15)N using Fourier-transform methods. The shift effects produced by several substituent groups are compared with corresponding substituent effects in amino acids, amino acid derivatives, and dipeptides. The results show that N-alkylethanamides are not especially good models for predicting ^(15)N shifts in dipeptides. The sensitivity of the ^(15)N shift of N-arylethanamides to electronic effects, as reflected in the Hammett p constant, is less than that of the ^(15)N shift in para-substituted benzenamines.

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Additional Information:© 1978 American Chemical Society. Received September 28, 1977. Supported by the National Science Foundation and by the Public Health Service, Research Grant No. GM-11073, from the Division of General Medical Sciences.
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U.S. Public Health Service (USPHS)GM-11073
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Caltech Gates and Crellin Laboratories of Chemistry5673
Issue or Number:6
Record Number:CaltechAUTHORS:20151008-070944093
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Official Citation:Nitrogen-15 magnetic resonance spectroscopy. Natural-abundance spectra of secondary amides Philip W. Westerman and John D. Roberts The Journal of Organic Chemistry 1978 43 (6), 1177-1179 DOI: 10.1021/jo00400a033
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60889
Deposited By: Ruth Sustaita
Deposited On:08 Oct 2015 19:00
Last Modified:10 Nov 2021 22:41

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