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pH-Dependent Conformational Switching in 2,6-Benzamidodiphenylacetylenes

Authors

  • Ian M. Jones,

    1. Department of Chemistry, Yale University, P.O. Box 20810 New Haven, CT 06520 (USA)
    2. University of Oxford, 12 Mansfield Rd. Oxford, OX1 3TA (UK)
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  • Dr. Hannah Lingard,

    1. Department of Chemistry, Yale University, P.O. Box 20810 New Haven, CT 06520 (USA)
    2. University of Oxford, 12 Mansfield Rd. Oxford, OX1 3TA (UK)
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  • Prof. Andrew D. Hamilton

    Corresponding author
    1. Department of Chemistry, Yale University, P.O. Box 20810 New Haven, CT 06520 (USA)
    2. University of Oxford, 12 Mansfield Rd. Oxford, OX1 3TA (UK)
    • Department of Chemistry, Yale University, P.O. Box 20810 New Haven, CT 06520 (USA)
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  • The authors would like to thank Dr. Sam Thompson (Oxford) and Prof. Marc Adler (N.I.U.) for helpful insights; Drs. Amber Thompson and Christopher Incarvito for crystallography; NSF (CHE-0750357) and the University of Oxford for funding.

Abstract

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The conformational equilibrium of a pH-dependent switch based on an intramolecularly H-bonded diphenylacetylene can be predictably biased by using electron-donating or -withdrawing groups (see scheme). Furthermore, protonation of the electron-donating dimethylamino group converts it into an electron-withdrawing dimethylammonium cation with a concomitant switch in conformation.

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