Molecular recognition of fluoride anion: Benzene-based tripodal imidazolium receptor

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

Research output: Contribution to journalArticlepeer-review

161 Scopus citations

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.

Original languageEnglish
Pages (from-to)2467-2470
Number of pages4
JournalJournal of Organic Chemistry
Volume68
Issue number6
DOIs
StatePublished - 21 Mar 2003

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