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Issue 30, 2019
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17O NMR and 15N NMR chemical shifts of sterically-hindered amides: ground-state destabilization in amide electrophilicity

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Abstract

The structure and spectroscopic properties of the amide bond are a topic of fundamental interest in chemistry and biology. Herein, we report 17O NMR and 15N NMR spectroscopic data for four series of sterically-hindered acyclic amides. Despite the utility of 17O NMR and 15N NMR spectroscopy, these methods are severely underutilized in the experimental determination of electronic properties of the amide bond. The data demonstrate that a combined use of 17O NMR and 15N NMR serves as a powerful tool in assessing electronic effects of the amide bond substitution as a measure of electrophilicity of the amide bond. Notably, we demonstrate that steric destabilization of the amide bond results in electronically-activated amides that are comparable in terms of electrophilicity to acyl fluorides and carboxylic acid anhydrides.

Graphical abstract: 17O NMR and 15N NMR chemical shifts of sterically-hindered amides: ground-state destabilization in amide electrophilicity

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Article information


Submitted
19 Feb 2019
Accepted
12 Mar 2019
First published
13 Mar 2019

Chem. Commun., 2019,55, 4423-4426
Article type
Communication
Author version available

17O NMR and 15N NMR chemical shifts of sterically-hindered amides: ground-state destabilization in amide electrophilicity

V. Pace, W. Holzer, L. Ielo, S. Shi, G. Meng, M. Hanna, R. Szostak and M. Szostak, Chem. Commun., 2019, 55, 4423
DOI: 10.1039/C9CC01402K

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