Stereodynamics of bond rotation in tertiary aromatic amides

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

    Research output: Contribution to journalArticlepeer-review


    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 pages10
    JournalChemistry - A European Journal
    Issue number6
    Publication statusPublished - 15 Mar 2002


    • Amides
    • Bond rotation
    • NMR spectroscopy
    • Saturation transfer


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