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

András Olasz, Pierre Mignon, Frank De Proft, T. Veszprémi, Paul Geerlings

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

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
Volume407
Issue number4-6
DOIs
Publication statusPublished - May 27 2005

Fingerprint

Phenol
Acidity
acidity
phenols
Phenols
Benzene
Discrete Fourier transforms
Conformations
Protons
interactions
Calibration
affinity
reactivity
benzene
protons
rings

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Surfaces and Interfaces
  • Condensed Matter Physics

Cite this

Effect of the π-π Stacking interaction on the acidity of phenol. / Olasz, András; Mignon, Pierre; De Proft, Frank; Veszprémi, T.; Geerlings, Paul.

In: Chemical Physics Letters, Vol. 407, No. 4-6, 27.05.2005, p. 504-509.

Research output: Contribution to journalArticle

Olasz, András ; Mignon, Pierre ; De Proft, Frank ; Veszprémi, T. ; Geerlings, Paul. / Effect of the π-π Stacking interaction on the acidity of phenol. In: Chemical Physics Letters. 2005 ; Vol. 407, No. 4-6. pp. 504-509.
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