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.
Bosmans, V. (Contributor), Poater, J. (Contributor), Hammink, R. (Contributor), Tinnemans, P. (Contributor), Bickelhaupt, F. (Contributor) & Mecinović, J. (Contributor), Unknown Publisher, 15 Mar 2019