Conformational communication between the Ar-CO and Ar-N axes in 2,2′-disubstituted benzanilides and their derivatives

Jonathan Clayden*, Lluís Vallverdú, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

22 Citations (Scopus)

Abstract

Benzanilides containing two or more potentially stereogenic amide axes exist in solution as mixtures of conformers which are detectable by NMR. For simple tertiary benzanilides carrying an ortho substituent on each ring, conformational control can be high (up to about 10: 1) providing the substituents are large, indicating that the two axes are in conformational communication with one another. For more complex diamides, conformational communication breaks down, and mixtures of conformers are evident by NMR.

Original languageEnglish
Pages (from-to)2106-2118
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number11
Early online date3 Apr 2006
DOIs
Publication statusPublished - 7 Jun 2006

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