Counterintuitive substituent effect of the ethynyl group in ion-pi interactions

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

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)


In this article, we report a high-level theoretical study (SCS-RI-MP2(full)/aug-cc-pVTZ) that deals with the substituent effect of the ethynyl group on ion-pi interactions in 1,3,5-triethynylbenzene systems. The ethynyl group is able to act as an electron-withdrawing group, thus favoring the anion-pi interaction. Unexpectedly, it has little influence on the cation-pi interaction. This behavior has been studied by examining the geometrical and energetic features of the complexes, AIM, and charge analyses and partitioning the interaction energy. The simultaneous interaction of 1,3,5-triethynylbenzene with cations and anions by opposite sides of the ring has also been studied.

Original languageEnglish
Pages (from-to)10367-10375
Number of pages9
JournalJournal of Physical Chemistry A
Issue number38
Early online date27 Aug 2009
Publication statusPublished - 24 Sept 2009


  • Benzene derivatives
  • Computer simulation
  • Crystallography, X-Ray
  • Models, Chemical
  • Models, Molecular
  • Quantum theory
  • Journal article
  • Research support, Non-U.S. Gov't


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