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Title: Electrophilicity Scale of Activated Amides: 17 O NMR and 15 N NMR Chemical Shifts of Acyclic Twisted Amides in N−C(O) Cross‐Coupling
Award ID(s):
1650766
PAR ID:
10224903
Author(s) / Creator(s):
; ; ; ; ; ;
Date Published:
Journal Name:
Chemistry – A European Journal
Volume:
26
Issue:
69
ISSN:
0947-6539
Page Range / eLocation ID:
16246 to 16250
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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  1. The structure and spectroscopic properties of the amide bond are a topic of fundamental interest in chemistry and biology. Herein, we report 17 O NMR and 15 N NMR spectroscopic data for four series of sterically-hindered acyclic amides. Despite the utility of 17 O NMR and 15 N 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 17 O NMR and 15 N 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. 
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