Conformation and stereodynamics of 2,2'-disubstituted N,N'-diaryl ureas. - Archive ouverte HAL Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2008

Conformation and stereodynamics of 2,2'-disubstituted N,N'-diaryl ureas.

Jonathan Clayden
  • Function : Author
Mark Pickworth
  • Function : Author
Lyn Jones
  • Function : Author

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.

Dates and versions

hal-00919186 , version 1 (16-12-2013)

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Jonathan Clayden, Loïc Lemiègre, Mark Pickworth, Lyn Jones. Conformation and stereodynamics of 2,2'-disubstituted N,N'-diaryl ureas.. Organic & Biomolecular Chemistry, 2008, 6 (16), pp.2908-13. ⟨10.1039/b802673d⟩. ⟨hal-00919186⟩
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