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J Org Chem. 2013 Mar 1;78(5):2099-103. doi: 10.1021/jo302265k. Epub 2012 Dec 10.

Intimate interactions with carbonyl groups: dipole-dipole or n→π*?

Author information

1
Department of Biochemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.

Abstract

Amide carbonyl groups in proteins can engage in C═O···C═O and C-X···C═O interactions, where X is a halogen. The putative involvement of four poles suggests that these interactions are primarily dipolar. Our survey of crystal structures with a C-X···C═O contact that is short (i.e., within the sum of the X and C van der Waals radii) revealed no preferred C-X···C═O dihedral angle. Moreover, we found that structures with a short X(-)···C═O contact display the signatures of an n→π* interaction. We conclude that intimate interactions with carbonyl groups do not require a dipole.

PMID:
23163960
PMCID:
PMC3586291
DOI:
10.1021/jo302265k
[Indexed for MEDLINE]
Free PMC Article

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