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

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

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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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.

Original languageEnglish
Pages (from-to)3632-3637
Number of pages6
JournalJournal of Organic Chemistry
Issue number6
Early online date22 Feb 2019
Publication statusPublished - 15 Mar 2019


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