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Issue 11, 2006
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Conformational communication between the Ar–CO and Ar–N axes in 2,2′-disubstituted benzanilides and their derivatives

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Abstract

Benzanilides containing two or more potentially stereogenic amide axes exist in solution as mixtures of conformers which are detectable by NMR. For simple tertiary benzanilides carrying an ortho substituent on each ring, conformational control can be high (up to about 10 : 1) providing the substituents are large, indicating that the two axes are in conformational communication with one another. For more complex diamides, conformational communication breaks down, and mixtures of conformers are evident by NMR.

Graphical abstract: Conformational communication between the Ar–CO and Ar–N axes in 2,2′-disubstituted benzanilides and their derivatives

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Supplementary files

Article information


Submitted
27 Feb 2006
Accepted
03 Apr 2006
First published
25 Apr 2006

Org. Biomol. Chem., 2006,4, 2106-2118
Article type
Paper

Conformational communication between the Ar–CO and Ar–N axes in 2,2′-disubstituted benzanilides and their derivatives

J. Clayden, L. Vallverdú and M. Helliwell, Org. Biomol. Chem., 2006, 4, 2106
DOI: 10.1039/B602912D

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