Aromatic rings act as hydrogen bond acceptors

https://doi.org/10.1016/0022-2836(88)90471-8Get rights and content

Abstract

Simple energy calculations show that there is a significant interaction between a hydrogen bond donor (like the > NH group) and the centre of a benzene ring, which acts as a hydrogen bond acceptor. This interaction, which is about half as strong as a normal hydrogen bond, contributes approximately 3kcal/mol (1 cal = 4.184 J) of stabilizing enthalpy and is expected to play a significant role in molecular associations. It is of interest that the aromatic hydrogen bond arises from small partial charges centred on the ring carbon and hydrogen atoms: there is no need to consider delocalized electrons. Although some energy calculations have included such partial charges, their role in forming such a strong interaction was not appreciated until after aromatic hydrogen bonds had been observed in protein-drug complexes.

References (16)

  • S.K. Burley et al.

    FEBS Letters

    (1986)
  • J. Singh et al.

    FEBS Letters

    (1985)
  • D.E. Williams et al.

    Comput. Chem

    (1977)
  • H.J.C. Berendsen et al.
  • S.K. Burley et al.

    Science

    (1985)
  • C.A. Coulson
  • A.T. Hagler et al.

    J. Amer. Chem. Soc

    (1974)
  • J. Hermans et al.

    Biopolymers

    (1984)
There are more references available in the full text version of this article.

Cited by (0)

M.F.P's work is supported by NIH grant no. HL31461 and NSF grant no. PCM 8312414.

On leave from the Department of Chemical Physics, Weizmann Institute, Rehovot 76100, Israel.

View full text