Title: Effect of the pi-pi stacking interaction on the acidity of phenol
Authors: Olasz, A ×
Mignon, Pierre
De Proft, Frank
Veszpremi, T
Geerlings, P #
Issue Date: 2005
Publisher: Elsevier science bv
Series Title: Chemical Physics Letters vol:407 issue:4-6 pages:504-509
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 pK(a) 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. (c) 2005 Elsevier B.V. All rights reserved.
ISSN: 0009-2614
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Non-KU Leuven Association publications
× corresponding author
# (joint) last author

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