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

Authors
Bragg, RA Clayden, J
Citation
Ra. Bragg et J. Clayden, Using symmetry to monitor geared bond rotation in aromatic amides by dynamic NMR, ORG LETT, 2(21), 2000, pp. 3351-3354
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
21
Year of publication
2000
Pages
3351 - 3354
Database
ISI
SICI code
1523-7060(20001019)2:21<3351:USTMGB>2.0.ZU;2-H
Abstract
[GRAPHICS] Dynamic NMR proves that the fastest interconversion between conformers of s imple tertiary aromatic amide 3 is racemization via a geared (correlated) r otation of both the Ar-CO and N-CO bonds. The symmetry of 3 is such that co rrelated and noncorrelated rotations are easily distinguishable, even witho ut assignment of the NMR spectrum, simply by observing the number of peaks taking part in the exchange.