Molecular Recognition of Fluoride Anion: Benzene-Based Tripodal Imidazolium Receptor
- 15 February 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (6), 2467-2470
- https://doi.org/10.1021/jo0263519
Abstract
A benzene-based tripodal imidazolium receptor utilizing the strong (C−H)+···X- hydrogen bonding interaction between imidazolium moieties and halide anions is extensively investigated both theoretically and experimentally. Ab initio calculations predict that this receptor has a very high affinity for fluoride ion (F-). The association constant and free energy gain of the N-butyl receptor 2 for F- in acetonitrile were measured to be 2.1 × 105 M-1 and −7.25 kcal/mol, respectively, showing that the receptor has a high affinity for F- in highly polar organic solvents.Keywords
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