The role of the ethynyl substituent on the π-π stacking affinity of benzene: a theoretical study

Xavier Lucas; David Quiñonero; Antonio Frontera; Pere M. Deyà

doi:10.1002/cphc.201000891

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

Biological Chemistry and Drug Discovery

Research output: Contribution to journal › Article › peer-review

4 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 language	English
Pages (from-to)	283-288
Number of pages	6
Journal	ChemPhysChem
Volume	12
Issue number	2
Early online date	22 Dec 2010
DOIs	https://doi.org/10.1002/cphc.201000891
Publication status	Published - 7 Feb 2011

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Journal article

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10.1002/cphc.201000891

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title = "The role of the ethynyl substituent on the π-π stacking affinity of benzene: a theoretical study",

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.",

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AU - Deyà, Pere M.

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AB - 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.

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The role of the ethynyl substituent on the π-π stacking affinity of benzene: a theoretical study

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