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The Role of the Ethynyl Substituent on the π–π Stacking Affinity of Benzene: A Theoretical Study

✍ Scribed by Xavier Lucas; Dr. David Quiñonero; Dr. Antonio Frontera; Prof. Dr. Pere M. Deyà

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
381 KB
Volume
12
Category
Article
ISSN
1439-4235

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✦ Synopsis

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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