An AAAA–DDDD quadruple hydrogen-bond array

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

Research output: Contribution to journalArticle

96 Citations (Scopus)

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 × 10(12) M(-1) in CH2Cl2, 1.5 × 10(6) M(-1) in CH3CN and 3.4 × 10(5) M(-1) in 10% v/v DMSO/CHCl3). The association constant in CH2Cl2 corresponds to a binding free energy (ΔG) 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.

LanguageEnglish
Pages244-48
Number of pages5
JournalNature Chemistry
Issue number3
DOIs
Publication statusPublished - 21 Feb 2011

Fingerprint

Hydrogen bonds
Carbon
Covalent bonds
Dimethyl Sulfoxide
Coulomb interactions
Free energy
Hydrogen
Thermodynamic stability
Association reactions
Molecules

Keywords

  • carbon
  • hydrogen
  • hydrogen bonding
  • solvents
  • spectrophotometry, Ultraviolet
  • static electricity
  • thermodynamics

Cite this

Blight, B. A., Hunter, C. A., Leigh, D. A., McNab, H., & Thomson, P. I. T. (2011). An AAAA–DDDD quadruple hydrogen-bond array. Nature Chemistry, (3), 244-48. https://doi.org/10.1038/nchem.987
Blight, Barry A. ; Hunter, Christopher A. ; Leigh, David A. ; McNab, Hamish ; Thomson, Patrick I. T. / An AAAA–DDDD quadruple hydrogen-bond array. In: Nature Chemistry. 2011 ; No. 3. pp. 244-48.
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Blight, BA, Hunter, CA, Leigh, DA, McNab, H & Thomson, PIT 2011, 'An AAAA–DDDD quadruple hydrogen-bond array' Nature Chemistry, no. 3, pp. 244-48. https://doi.org/10.1038/nchem.987

An AAAA–DDDD quadruple hydrogen-bond array. / Blight, Barry A.; Hunter, Christopher A.; Leigh, David A.; McNab, Hamish; Thomson, Patrick I. T.

In: Nature Chemistry, No. 3, 21.02.2011, p. 244-48.

Research output: Contribution to journalArticle

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