Literature DB >> 3172202

Aromatic rings act as hydrogen bond acceptors.

M Levitt1, M F Perutz.   

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.

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Year:  1988        PMID: 3172202     DOI: 10.1016/0022-2836(88)90471-8

Source DB:  PubMed          Journal:  J Mol Biol        ISSN: 0022-2836            Impact factor:   5.469


  94 in total

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9.  Exploring atomistic details of pH-dependent peptide folding.

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10.  A synthetic lectin for O-linked beta-N-acetylglucosamine.

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