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Building a Better Halide Receptor: Optimum Choice of Spacer, Binding Unit, and Halosubstitution
Author(s) -
Nepal Binod,
Scheiner Steve
Publication year - 2016
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201501149
Subject(s) - halide , carbazole , chemistry , thiophene , benzene , binding energy , crystallography , stereochemistry , computational chemistry , photochemistry , inorganic chemistry , organic chemistry , physics , nuclear physics
Quantum calculations are used to measure the binding of halides to a number of bipodal dicationic receptors, constructed as a pair of binding units separated by a spacer group. A number of variations are studied. A H atom on each binding unit (imidazolium or triazolium) is replaced by Br or I. Benzene, thiophene, carbazole, and dimethylnaphthalene are considered as spacer groups. Each receptor is paired with halides F − , Cl − , Br − , and I − . Substitution with I on the binding unit yields a large enhancement of binding, as much as 13 orders of magnitude; a much smaller increase occurs for substitution with Br. Imidazolium is a more effective binding agent than is triazolium. Benzene and dimethylnaphthalene represent the best spacers, followed by thiophene and carbazole. F − binds much more strongly than do the other halides, which obey the order Cl − >Br − >I − .