Aromatic rings act as hydrogen bond acceptors

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 approximatel...

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Published inJournal of molecular biology Vol. 201; no. 4; pp. 751 - 754
Main Authors Levitt, Michael, Perutz, Max F.
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 20.06.1988
Elsevier
Subjects
Benzene
Biological and medical sciences
Chemical Phenomena
Chemistry, Physical
Fundamental and applied biological sciences. Psychology
Hydrogen Bonding
hydrogen bonds
Interactions. Associations
Intermolecular phenomena
Molecular biophysics
proteins
Thermodynamics
Drug
Proteins
Molecular interaction
Molecular complex
Aromatic compound
Hydrogen bond
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-2836
1089-8638
DOI:10.1016/0022-2836(88)90471-8