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

104 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.

Original languageEnglish
Pages (from-to)244-48
Number of pages5
JournalNature Chemistry
Issue number3
DOIs
Publication statusPublished - 21 Feb 2011

Keywords

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

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  • Research Output

    • 104 Citations
    • 1 Doctoral Thesis

    Extremely strong contiguous hydrogen bonding arrays

    Thomson, P., 29 Jun 2013, Edinburgh. 173 p.

    Research output: ThesisDoctoral Thesis

  • 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