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Combined Cation–π and Anion–π Interactions for Zwitterion Recognition

Authors

  • Olivier Perraud,

    1. Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, 69364 Lyon (France)
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  • Prof. Vincent Robert,

    1. Laboratoire de Chimie Quantique, Institut de Chimie, UMR 7177, Université de Strasbourg, 4, rue Blaise Pascal, 67070 Strasbourg (France)
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  • Prof. Heinz Gornitzka,

    1. Laboratoire de Chimie de Coordination, UPR 8241, 205, route de Narbonne, 31077 Toulouse (France)
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  • Dr. Alexandre Martinez,

    Corresponding author
    1. Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, 69364 Lyon (France)
    • Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, 69364 Lyon (France)
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  • Dr. Jean-Pierre Dutasta

    Corresponding author
    1. Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, 69364 Lyon (France)
    • Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, 69364 Lyon (France)
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Abstract

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Brothers and enemies: Anion–π and cation–π interactions act in a synergistic way when gathered in the molecular cavity of a hemicryptophane host, affording an efficient contribution (−170 kJ mol−1) in zwitterion recognition. NMR titration experiments and calculations reveal the positioning of the guest in the cavity of the heteroditopic receptor. This study emphasizes the importance of anion–π bonds in host–guest chemistry.

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