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Halogen Bonding between Anions and Iodoperfluoroorganics: Solution-Phase Thermodynamics and Multidentate-Receptor Design

Authors

  • Mohammed G. Sarwar,

    1. Department of Chemistry, Lash Miller Laboratories, University of Toronto, 80 St George St., Toronto ON M5S 3H6 (Canada), Fax: (+1) 416-978-8775
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  • Bojan Dragisić,

    1. Department of Chemistry, Lash Miller Laboratories, University of Toronto, 80 St George St., Toronto ON M5S 3H6 (Canada), Fax: (+1) 416-978-8775
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  • Elena Dimitrijević,

    1. Department of Chemistry, Lash Miller Laboratories, University of Toronto, 80 St George St., Toronto ON M5S 3H6 (Canada), Fax: (+1) 416-978-8775
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  • Prof. Mark S. Taylor

    Corresponding author
    1. Department of Chemistry, Lash Miller Laboratories, University of Toronto, 80 St George St., Toronto ON M5S 3H6 (Canada), Fax: (+1) 416-978-8775
    • Department of Chemistry, Lash Miller Laboratories, University of Toronto, 80 St George St., Toronto ON M5S 3H6 (Canada), Fax: (+1) 416-978-8775
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Abstract

The interactions of iodoperfluoroarenes and -alkanes with anions in organic solvent were studied. The data indicates that favorable halogen-bonding interactions exist between halide anions and the monodentate model compounds C6F5I and C8F17I. These data served as a basis for the development of preorganized multidentate receptors capable of high-affinity anion recognition. Several new receptor architectures were prepared, and the multidentate-iodoperfluorobenzoate-ester design, as described in a preliminary communication, was evaluated in more detail. Computation was employed to better interpret the structure–activity relationships arising from these studies. Investigations of the thermodynamics of anion binding (by van't Hoff analysis) and solvent effects reveal details of these halogen bonding interactions.

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