Using symmetry to monitor geared bond rotation in aromatic amides by dynamic NMR

Ryan A. Bragg, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

25 Citations (Scopus)

Abstract

(matrix presented) Dynamic NMR proves that the fastest interconversion between conformers of simple tertiary aromatic amide 3 is racemization via a geared (correlated) rotation of both the Ar-CO and N-CO bonds. The symmetry of 3 is such that correlated and noncorrelated rotations are easily distinguishable, even without assignment of the NMR spectrum, simply by observing the number of peaks taking part in the exchange.

Original languageEnglish
Pages (from-to)3351-3354
Number of pages4
JournalOrganic Letters
Volume2
Issue number21
Early online date14 Sep 2000
DOIs
Publication statusPublished - 19 Oct 2000

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