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Cited by 466

The DOI matches its Crossref record; 60 of the 60 references it cites were found in a registry or an index.

Local Nature of Substituent Effects in Stacking Interactions

Open access
Wheeler, Steven E.·2011·Journal of the American Chemical Society
DOI 10.1021/ja202932e
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Abstract

Popular explanations of substituent effects in π-stacking interactions hinge upon substituent-induced changes in the aryl π-system. This entrenched view has been used to explain substituent effects in countless stacking interactions over the past 2 decades. However, for a broad range of stacked dimers, it is shown that substituent effects are better described as arising from local, direct interactions of the substituent with the proximal vertex of the other ring. Consequently, substituent effects in stacking interactions are additive, regardless of whether the substituents are on the same or opposite rings. Substituent effects are also insensitive to the introduction of heteroatoms on distant parts of either stacked ring. This local, direct interaction viewpoint provides clear, unambiguous explanations of substituent effects for myriad stacking interactions that are in accord with robust computational data, including DFT-D and new benchmark CCSD(T) results. Many of these computational results cannot be readily explained using traditional π-polarization-based models. Analyses of stacking interactions based solely on the sign of the electrostatic potential above the face of an aromatic ring or the molecular quadrupole moment face a similar fate. The local, direct interaction model provides a simple means of analyzing substituent effects in complex aromatic systems and also offers simple explanations of the crystal packing of fluorinated benzenes and the recently published dependence of the stability of protein-RNA complexes on the regiochemistry of fluorinated base analogues [J. Am. Chem. Soc.2011, 133, 3687-3689].

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Metadata

Authors
Wheeler, S. E.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2011-06-09
Volume
133
Issue
26
Pages
10262-10274
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja202932e
OpenAlex
W2326385719
Cited by
466
References
60
FWCI
23.28
Type
journal article
Language
en
Open access
hybrid

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