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Molecular Recognition of Fluoride Anion:  Benzene-Based Tripodal Imidazolium Receptor

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journal contribution
posted on 15.02.2003, 00:00 by Sunggoo Yun, Hyejae Ihm, Heon Gon Kim, Chi-Wan Lee, Bandyopadhyay Indrajit, Kyung Seok Oh, Young Jun Gong, Jung Woo Lee, Juyoung Yoon, Hee Cheon Lee, Kwang S. Kim
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.