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Halogen Bonding between Anions and Iodoperfluoroorganics: Solution‐Phase Thermodynamics and Multidentate‐Receptor Design
Author(s) -
Sarwar Mohammed G.,
Dragisić Bojan,
Dimitrijević Elena,
Taylor Mark S.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202689
Subject(s) - denticity , halogen bond , halide , chemistry , halogen , solvent , phase (matter) , computational chemistry , ion , thermodynamics , stereochemistry , inorganic chemistry , crystallography , organic chemistry , crystal structure , alkyl , physics
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 C 6 F 5 I and C 8 F 17 I. 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.