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 - Tarakeshwar, P.
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.
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U2 - 10.1021/jo016335w
DO - 10.1021/jo016335w
M3 - Article
C2 - 11895402
AN - SCOPUS:0037155538
SN - 0022-3263
VL - 67
SP - 1848
EP - 1851
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -