An AAAA-DDDD quadruple hydrogen-bond array

Barry A. Blight; Christopher A. Hunter; David A. Leigh; Hamish McNab; Patrick I. T. Thomson

doi:10.1038/NCHEM.987

An AAAA-DDDD quadruple hydrogen-bond array

Barry A. Blight, Christopher A. Hunter, David A. Leigh, Hamish McNab, Patrick I. T. Thomson

School of Chemistry

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Abstract

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.

Original language	English
Pages (from-to)	244-248
Number of pages	5
Journal	Nature Chemistry
Volume	3
Issue number	3
DOIs	https://doi.org/10.1038/NCHEM.987
Publication status	Published - Mar 2011

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title = "An AAAA-DDDD quadruple hydrogen-bond array",

abstract = "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.",

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T1 - An AAAA-DDDD quadruple hydrogen-bond array

AU - Blight, Barry A.

AU - Hunter, Christopher A.

AU - Leigh, David A.

AU - McNab, Hamish

AU - Thomson, Patrick I. T.

PY - 2011/3

Y1 - 2011/3

N2 - 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.

AB - 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.

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JO - Nature Chemistry

JF - Nature Chemistry

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An AAAA-DDDD quadruple hydrogen-bond array

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