The role of the ethynyl substituent on the π-π stacking affinity of benzene

a theoretical study

Xavier Lucas (Lead / Corresponding author), David Quiñonero, Antonio Frontera (Lead / Corresponding author), Pere M. Deyà

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Herein, we report a high-level theoretical study (SCS-RI-MP2(full)/aug-cc-pVTZ) examining the stacking affinity of 1,3,5-triethynylbenzene. The stacking properties of this compound are compared to those of benzene and 1,3,5-trifluorobenzene. The results indicate that the ethynyl substituent improves the stacking affinity of the arene, since the binding energies for the stacked ethynyl-substituted arene dimers are higher than those of both benzene and the fluoro-substituted arene. This interesting behaviour has been studied by examining the energetics, geometries and electron charge density features of the complexes. A query in the Cambridge Structural Database returned several X-ray crystal structures containing π-π stacking interactions of 1,3,5-triethynylaryls that strongly agree with the theoretical results.

Original languageEnglish
Pages (from-to)283-288
Number of pages6
JournalChemPhysChem
Volume12
Issue number2
Early online date22 Dec 2010
DOIs
Publication statusPublished - 7 Feb 2011

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Benzene
affinity
benzene
Charge density
Binding energy
Dimers
Crystal structure
binding energy
dimers
X rays
crystal structure
Geometry
Electrons
geometry
electrons
x rays
interactions
1,3,5-trifluorobenzene

Keywords

  • Journal article

Cite this

Lucas, Xavier ; Quiñonero, David ; Frontera, Antonio ; Deyà, Pere M. / The role of the ethynyl substituent on the π-π stacking affinity of benzene : a theoretical study. In: ChemPhysChem. 2011 ; Vol. 12, No. 2. pp. 283-288.
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The role of the ethynyl substituent on the π-π stacking affinity of benzene : a theoretical study. / Lucas, Xavier (Lead / Corresponding author); Quiñonero, David; Frontera, Antonio (Lead / Corresponding author); Deyà, Pere M.

In: ChemPhysChem, Vol. 12, No. 2, 07.02.2011, p. 283-288.

Research output: Contribution to journalArticle

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