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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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Publication details

The article was received on 27 Feb 2006, accepted on 03 Apr 2006 and first published on 25 Apr 2006


Article type: Paper
DOI: 10.1039/B602912D
Citation: Org. Biomol. Chem., 2006,4, 2106-2118
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    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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