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Issue 16, 2008
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Conformation and stereodynamics of 2,2′-disubstituted N,N′-diaryl ureas

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Abstract

Except in the most hindered of cases, N,N′-diaryl N,N′-dimethyl ureas adopt a conformation with the two aryl rings disposed cis to one another. Variable temperature NMR studies reveal the rate at which the Ar–N bonds rotate as well as the conformational preference of ortho disubstituted ureas in which more than one cis orientation is possible. In general, a conformation in which the aryl rings lie close in space but with their most bulky 2-substituents aligned anti is preferred, but with particularly bulky 2-substituents, conformations in which one of the aryl rings points away from the other may also be populated.

Graphical abstract: Conformation and stereodynamics of 2,2′-disubstituted N,N′-diaryl ureas

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Article information


Submitted
18 Feb 2008
Accepted
13 May 2008
First published
16 Jun 2008

Org. Biomol. Chem., 2008,6, 2908-2913
Article type
Paper

Conformation and stereodynamics of 2,2′-disubstituted N,N′-diaryl ureas

J. Clayden, L. Lemiègre, M. Pickworth and L. Jones, Org. Biomol. Chem., 2008, 6, 2908
DOI: 10.1039/B802673D

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