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PMID: 3172202 Published · ppublish English Comparative Study Journal Article Research Support, U.S. Gov't, Non-P.H.S. Research Support, U.S. Gov't, P.H.S.

Aromatic rings act as hydrogen bond acceptors.

Journal of molecular biology ·Vol. 201 ·No. 4 ·1988-06-20 ·Pages 751-4

Levitt M, Perutz MF

Abstract

Simple energy calculations show that there is a significant interaction between a hydrogen bond donor (like the greater than 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 3 kcal/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.

MeSH Terms
Benzene Chemical Phenomena Chemistry, Physical Hydrogen Bonding Thermodynamics
Chemicals
Benzene
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Levitt M
MRC Laboratory of Molecular Biology, Cambridge, England.
Perutz M F
Article Info
Journal
Journal of molecular biology
Abbr.
J Mol Biol
ISSN
0022-2836
Published
1988-06-20
Pages
751-4
Language
English
Region
England
NLM ID
2985088R
Subset
IM
Grants
NHLBI NIH HHS · HL31461 · United States
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