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An AAAA–DDDD quadruple hydrogen-bond array

Blight, Barry A., Hunter, Christopher A., Leigh, David A., McNab, Hamish, Thomson, Patrick I. T. (2011) An AAAA–DDDD quadruple hydrogen-bond array. Nature Chemistry, 3 . pp. 244-248. ISSN 1755-4330. (doi:10.1038/nchem.987) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided. (Contact us about this Publication)
Official URL
http://dx.doi.org/10.1038/nchem.987

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 (Ka > 3 × 1012 M–1 in CH2Cl2, 1.5 × 106 M–1 in CH3CN and 3.4 × 105 M–1 in 10% v/v DMSO/CHCl3). The association constant in CH2Cl2 corresponds to a binding free energy (?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.

Item Type: Article
DOI/Identification number: 10.1038/nchem.987
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences
Depositing User: B. Blight
Date Deposited: 12 Nov 2014 23:33 UTC
Last Modified: 29 May 2019 13:27 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/44352 (The current URI for this page, for reference purposes)
Blight, Barry A.: https://orcid.org/0000-0003-1166-6206
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