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

doi:10.1021/jo0263519

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

164 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 language	English
Pages (from-to)	2467-2470
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	68
Issue number	6
DOIs	https://doi.org/10.1021/jo0263519
State	Published - 21 Mar 2003

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title = "Molecular recognition of fluoride anion: Benzene-based tripodal imidazolium receptor",

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.",

author = "Sunggoo Yun and Hyejae Ihm and Kim, {Heon Gon} and Lee, {Chi Wan} and Bandyopadhyay Indrajit and Oh, {Kyung Seok} and Gong, {Young Jun} and Lee, {Jung Woo} and Juyoung Yoon and Lee, {Hee Cheon} and Kim, {Kwang S.}",

year = "2003",

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doi = "10.1021/jo0263519",

language = "English",

volume = "68",

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journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - Molecular recognition of fluoride anion

T2 - Benzene-based tripodal imidazolium receptor

AU - Yun, Sunggoo

AU - Ihm, Hyejae

AU - Kim, Heon Gon

AU - Lee, Chi Wan

AU - Indrajit, Bandyopadhyay

AU - Oh, Kyung Seok

AU - Gong, Young Jun

AU - Lee, Jung Woo

AU - Yoon, Juyoung

AU - Lee, Hee Cheon

AU - Kim, Kwang S.

PY - 2003/3/21

Y1 - 2003/3/21

N2 - 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.

AB - 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.

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U2 - 10.1021/jo0263519

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SP - 2467

EP - 2470

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

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

Abstract

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