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

Jonathan Clayden*, Loïc Lemiègre, Mark Pickworth, Lyn Jones

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

25 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2908-2913
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume6
Issue number16
DOIs
Publication statusPublished - 16 Jun 2008

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