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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day = "21",

doi = "10.1021/jo0263519",

language = "English",

volume = "68",

pages = "2467--2470",

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.

UR - https://www.scopus.com/pages/publications/0037459671

U2 - 10.1021/jo0263519

DO - 10.1021/jo0263519

M3 - Article

C2 - 12636418

AN - SCOPUS:0037459671

SN - 0022-3263

VL - 68

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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