An AAAA-DDDD quadruple hydrogen-bond array

被引：128

作者：

Blight, Barry A. ^{[1
]}

Hunter, Christopher A. ^{[2
]}

Leigh, David A. ^{[1
]}

McNab, Hamish ^{[1
]}

Thomson, Patrick I. T. ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

[2] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

NATURE CHEMISTRY | 2011年 / 3卷 / 03期

基金：

英国工程与自然科学研究理事会;

关键词：

SECONDARY INTERACTIONS; MOLECULAR RECOGNITION; STABILITY; ASSOCIATION; COMPLEXES; CYTOSINE; MODULES;

D O I：

10.1038/NCHEM.987

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Secondary electrostatic interactions between adjacent hydrogen bonds can have a significant effect on the stability of a supramolecular complex. In theory, the binding strength should be maximized if all the hydrogen-bond donors (D) are on one component and all the hydrogen-bond acceptors (A) are on the other. Here, we describe a readily accessible AAAA-DDDD quadruple hydrogen-bonding array that exhibits exceptionally strong binding for a small-molecule hydrogen-bonded complex in a range of different solvents (K-a > 3 x 10(12) M-1 in CH2Cl2, 1.5 x 10(6) M-1 in CH3CN and 3.4 x 10(5) M-1 in 10% v/v DMSO/CHCl3). The association constant in CH2Cl2 corresponds to a binding free energy (Delta G) in excess of -71 kJ mol(-1) (more than 20% of the thermodynamic stability of a carbon-carbon covalent bond), which is remarkable for a supramolecular complex held together by just four intercomponent hydrogen bonds.

引用

页码：244 / 248

页数：5

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