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Cited by 587

The DOI matches its Crossref record; 24 of the 24 references it cites were found in a registry or an index.

Lone Pair−Aromatic Interactions: To Stabilize or Not to Stabilize

Egli, Martin, Sarkhel, Sanjay·2007·Accounts of Chemical Research
DOI 10.1021/ar068174u
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Abstract

The ability of aromatic rings to act as acceptors in hydrogen bonds has been demonstrated extensively both by experimental and by theoretical means. Countless examples of D-H...pi (H...pi, D = O, N, C) interactions have been found in the three-dimensional structures of proteins. Much less is known with regard to the occurrence of other possible noncovalent interactions with aromatics in macromolecular structures, those with a geometry that points oxygen lone pairs into the face of a pi system. There has been a growing interest in such lp...pi interactions in recent years, but the binding energies have mostly been studied using small-molecule model systems. We have conducted a survey of lp...pi interactions in crystal structures of DNA, RNA, and proteins and used ab initio calculations to estimate their energies. Our results demonstrate that such interactions are more common in nucleic acids and that significant binding energies only result when the aromatic system is positively polarized, for example, due to protonation of a nucleobase.

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Metadata

Authors
Egli, M., & Sarkhel, S.
Venue
Accounts of Chemical Research
Publisher
American Chemical Society (ACS)
Published
2006-12-15
Volume
40
Issue
3
Pages
197-205
ISSN
  • 0001-4842 (ISSN-L)
  • 1520-4898
DOI
10.1021/ar068174u
OpenAlex
W2134493054
Cited by
587
References
24
FWCI
14.69
Type
journal article
Language
en
Open access
closed

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