Stereodynamics of bond rotation in tertiary aromatic amides

Ryan A. Bragg, Jonathan Clayden*, Gareth A. Morris, Jennifer H. Pink

*Corresponding author for this work

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

63 Citations (Scopus)

Abstract

The degree to which the rotations about the C-N and Ar-CO bonds of aromatic amides occur in a concerted manner was investigated by a variety of NMR and kinetic techniques. Otherwise complex kinetic analyses were simplified by exploiting symmetry and asymmetry in the N-substituents of amides. In 2-unsubstituted 1-naphthamides bearing branched N-substituents, most conformational changes about the amide group were by correlated rotation, though uncorrelated Ar-CO rotation also occurred to some extent. In 2-substituted 1- naphthamides, correlated rotation accounted for all of the Ar-CO rotations, though a significant amount of uncorrelated C-N rotation also occured. Naphthamides bearing branched N-substituents thus turn out to be efficient molecular gears: Compound 12 showed almost no gear slippage.

Original languageEnglish
Pages (from-to)1279-1289
Number of pages11
JournalChemistry - A European Journal
Volume8
Issue number6
Early online date6 Mar 2002
DOIs
Publication statusPublished - 15 Mar 2002

Keywords

  • Amides
  • Bond rotation
  • NMR spectroscopy
  • Saturation transfer

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