Effect of the π-π Stacking interaction on the acidity of phenol

András Olasz, Pierre Mignon, Frank De Proft, Tamás Veszprémi, Paul Geerlings

Research output: Contribution to journalArticle

40 Citations (Scopus)


Stacked complexes made of phenol and substituted benzenes are studied via MP2 calculations in order to investigate the influence of the stacking interaction on the acidity of phenol. Aqueous-phase proton affinities have been computed and converted to pKa values using a calibration procedure involving a set of substituted phenols. Both T-shaped and parallel-displaced conformations lead to an appreciable decrease in the pKa, with the largest effect found for T-shaped arrangements. Local and global DFT based reactivity descriptors are used to analyze the effect of the stacking partner as well as the interaction between the aromatic rings.

Original languageEnglish
Pages (from-to)504-509
Number of pages6
JournalChemical Physics Letters
Issue number4-6
Publication statusPublished - May 27 2005

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

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