Conformation and stereodynamics of 2,2'-disubstituted N,N'-diaryl ureas |
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Authors: | Clayden Jonathan Lemiègre Loïc Pickworth Mark Jones Lyn |
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Affiliation: | School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK. clayden@man.ac.uk |
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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. |
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