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

Vera Bosmans, Jordi Poater, Roel Hammink, Paul Tinnemans, F. Matthias Bickelhaupt, Jasmin Mecinović*

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Abstrakt

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.
OriginalsprogEngelsk
TidsskriftThe Journal of Organic Chemistry
Vol/bind84
Udgave nummer6
Sider (fra-til)3632-3637
ISSN0022-3263
DOI
StatusUdgivet - 22. feb. 2019

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