Redox-induced conformational alteration of n,n-diarylamides

Org Lett. 2007 Dec 20;9(26):5545-7. doi: 10.1021/ol702504x. Epub 2007 Nov 16.

Abstract

We constructed a novel molecular conformational alteration system with an N-aryl-N-phenylacetamide structure, in which the N-aryl group consists of a hydroquinone-p-quinone system as a redox-dependent aromatic trigger. The amide conformation depended on the oxidation state of the aryl group, and the two states (compounds 2 and 3) were reversibly converted to each other by redox reactions. Such compounds would be applied as useful structural units for external stimulus-responsive control on the shape and function of large molecules or supramolecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Oxidation-Reduction

Substances

  • Amides