Using dipoles to control the directionality of functional groups: Syn- and anti-oriented benzene-1,3-dicarboxamides

Mark S. Betson, Jonathan Clayden, Ho Kam Lam, Madeleine Helliwell

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Poles apart: The relative orientation of a pair of functional groups-amides in this case-can be controlled by the choice of the substituent that lies between them. Groups which are effectively cylindrically symmetrical (Me, Cl) allow direct interaction between the dipoles of the amides and induce an anti orientation, whereas polar groups (OCOR, OSO2R, SO2R) interact with the dipole of both amides to yield a syn orientation (see picture). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Original languageEnglish
    Pages (from-to)1241-1244
    Number of pages3
    JournalAngewandte Chemie - International Edition
    Volume44
    Issue number8
    DOIs
    Publication statusPublished - 11 Feb 2005

    Keywords

    • Amides
    • Conformation analysis
    • Dipoles
    • Electrostatic interactions

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