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Probing Through-Space Polar−π Interactions in 2,6-Diarylphenols

Author:
Bosmans, Vera, Poater, Jordi, Hammink, Roel, Tinnemans, Paul, Bickelhaupt, F. Matthias, Mecinović, Jasmin
Source:
Journal of organic chemistry 2019 v.84 no.6 pp. 3632-3637
ISSN:
1520-6904
Subject:
acidity, chemical reactions, chemical structure, organic chemistry, phenol
Abstract:
Although it is well established that the acidity of phenol can be fine-tuned with substituents on its aromatic ring via through-bond effects, the role of through-space effects on the acidity of phenols is presently poorly understood. Here, we present integrated experimental and computational studies on substituted 2,6-diarylphenols that demonstrate the essential contribution from through-space OH−π interactions and O––π interactions in the observed trends in proton affinities and acidities of 2,6-diarylphenols.
Agid:
6326732