Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 6, Pages 2050-2058Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201202689
Keywords
anions; molecular recognition; noncovalent interactions; perfluoroarenes; thermodynamics
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Funding
- NSERC
- Canada Foundation for Innovation
- Canada Foundation for Innovation [19119]
- Ontario Ministry of Research and Innovation
- Province of Ontario
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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 structureactivity relationships arising from these studies. Investigations of the thermodynamics of anion binding (by van'tHoff analysis) and solvent effects reveal details of these halogen bonding interactions.
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