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Updated: May 1, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Stereodynamics of bond rotation in tertiary aromatic amides
Ryan A Bragg1, Jonathan Clayden, Gareth A Morris
1Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK.
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 occurred. Naphthamides bearing branched N-substituents thus turn out to be efficient molecular gears: Compound 12 showed almost no gear slippage.
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