TY - JOUR
T1 - Probing Through-Space Polar-π Interactions in 2,6-Diarylphenols
AU - Bosmans, Vera
AU - Poater, Jordi
AU - Hammink, Roel
AU - Tinnemans, Paul
AU - Bickelhaupt, F. Matthias
AU - Mecinović, Jasmin
N1 - Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/3/15
Y1 - 2019/3/15
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/85062831066
U2 - 10.1021/acs.joc.8b03147
DO - 10.1021/acs.joc.8b03147
M3 - Article
C2 - 30794409
AN - SCOPUS:85062831066
SN - 0022-3263
VL - 84
SP - 3632
EP - 3637
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -