A new type of ionophore family utilizing the cation-olefinic π interaction: Theoretical study of [n]beltenes

Soon Choi Hyuk, Dongwook Kim, Tarakeshwar Pilarisetty, Bum Suh Seung, Kwang S. Kim

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The possible utilization of [n]beltenes as a new family of ionophores, which exhibit a cation-olefinic π type of interaction in contrast to the cation-aromatic π type of interaction exhibited by [n]collarenes, has been investigated using both ab initio calculations and molecular dynamic simulations. Like [n]collarenes, n ethene groups are linked by -CH2- linkages in the [n]beltenes. Our calculations indicate that these [n]beltenes exhibit strong binding affinities and high selectivity for alkali metal cations ([5]beltene to Li+, [6]beltene to Na+, [7]beltene to Na+ and K+, [8]beltene to K+ and Rb+, and [9]beltene to Cs+ and Rb+). Compared to [n]collarenes, [n]beltenes are expected to have a finer ion selectivity because their cavity sizes can be varied with integral number n, while that of the former can be varied with an even number n. Suitable substituents could be employed to enhance both the binding and specificity of various sizes of [n]beltenes to different cations, as well as to increase the solubility.

Original languageEnglish (US)
Pages (from-to)1848-1851
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number6
DOIs
StatePublished - Mar 22 2002
Externally publishedYes

Fingerprint

Ionophores
Cations
Alkali Metals
Molecular dynamics
Solubility
Ions
Computer simulation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A new type of ionophore family utilizing the cation-olefinic π interaction : Theoretical study of [n]beltenes. / Hyuk, Soon Choi; Kim, Dongwook; Pilarisetty, Tarakeshwar; Seung, Bum Suh; Kim, Kwang S.

In: Journal of Organic Chemistry, Vol. 67, No. 6, 22.03.2002, p. 1848-1851.

Research output: Contribution to journalArticle

Hyuk, Soon Choi ; Kim, Dongwook ; Pilarisetty, Tarakeshwar ; Seung, Bum Suh ; Kim, Kwang S. / A new type of ionophore family utilizing the cation-olefinic π interaction : Theoretical study of [n]beltenes. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 6. pp. 1848-1851.
@article{f0fef64f5d31401cb41dcd97d6ab5be0,
title = "A new type of ionophore family utilizing the cation-olefinic π interaction: Theoretical study of [n]beltenes",
abstract = "The possible utilization of [n]beltenes as a new family of ionophores, which exhibit a cation-olefinic π type of interaction in contrast to the cation-aromatic π type of interaction exhibited by [n]collarenes, has been investigated using both ab initio calculations and molecular dynamic simulations. Like [n]collarenes, n ethene groups are linked by -CH2- linkages in the [n]beltenes. Our calculations indicate that these [n]beltenes exhibit strong binding affinities and high selectivity for alkali metal cations ([5]beltene to Li+, [6]beltene to Na+, [7]beltene to Na+ and K+, [8]beltene to K+ and Rb+, and [9]beltene to Cs+ and Rb+). Compared to [n]collarenes, [n]beltenes are expected to have a finer ion selectivity because their cavity sizes can be varied with integral number n, while that of the former can be varied with an even number n. Suitable substituents could be employed to enhance both the binding and specificity of various sizes of [n]beltenes to different cations, as well as to increase the solubility.",
author = "Hyuk, {Soon Choi} and Dongwook Kim and Tarakeshwar Pilarisetty and Seung, {Bum Suh} and Kim, {Kwang S.}",
year = "2002",
month = "3",
day = "22",
doi = "10.1021/jo016335w",
language = "English (US)",
volume = "67",
pages = "1848--1851",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "6",

}

TY - JOUR

T1 - A new type of ionophore family utilizing the cation-olefinic π interaction

T2 - Theoretical study of [n]beltenes

AU - Hyuk, Soon Choi

AU - Kim, Dongwook

AU - Pilarisetty, Tarakeshwar

AU - Seung, Bum Suh

AU - Kim, Kwang S.

PY - 2002/3/22

Y1 - 2002/3/22

N2 - The possible utilization of [n]beltenes as a new family of ionophores, which exhibit a cation-olefinic π type of interaction in contrast to the cation-aromatic π type of interaction exhibited by [n]collarenes, has been investigated using both ab initio calculations and molecular dynamic simulations. Like [n]collarenes, n ethene groups are linked by -CH2- linkages in the [n]beltenes. Our calculations indicate that these [n]beltenes exhibit strong binding affinities and high selectivity for alkali metal cations ([5]beltene to Li+, [6]beltene to Na+, [7]beltene to Na+ and K+, [8]beltene to K+ and Rb+, and [9]beltene to Cs+ and Rb+). Compared to [n]collarenes, [n]beltenes are expected to have a finer ion selectivity because their cavity sizes can be varied with integral number n, while that of the former can be varied with an even number n. Suitable substituents could be employed to enhance both the binding and specificity of various sizes of [n]beltenes to different cations, as well as to increase the solubility.

AB - The possible utilization of [n]beltenes as a new family of ionophores, which exhibit a cation-olefinic π type of interaction in contrast to the cation-aromatic π type of interaction exhibited by [n]collarenes, has been investigated using both ab initio calculations and molecular dynamic simulations. Like [n]collarenes, n ethene groups are linked by -CH2- linkages in the [n]beltenes. Our calculations indicate that these [n]beltenes exhibit strong binding affinities and high selectivity for alkali metal cations ([5]beltene to Li+, [6]beltene to Na+, [7]beltene to Na+ and K+, [8]beltene to K+ and Rb+, and [9]beltene to Cs+ and Rb+). Compared to [n]collarenes, [n]beltenes are expected to have a finer ion selectivity because their cavity sizes can be varied with integral number n, while that of the former can be varied with an even number n. Suitable substituents could be employed to enhance both the binding and specificity of various sizes of [n]beltenes to different cations, as well as to increase the solubility.

UR - http://www.scopus.com/inward/record.url?scp=0037155538&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037155538&partnerID=8YFLogxK

U2 - 10.1021/jo016335w

DO - 10.1021/jo016335w

M3 - Article

C2 - 11895402

AN - SCOPUS:0037155538

VL - 67

SP - 1848

EP - 1851

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 6

ER -