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

The Journal of Organic Chemistry
Vera BosmansJasmin Mecinović

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.

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
Apr 20, 2001·Journal of Applied Microbiology·R Puupponen-PimiäK M Oksman-Caldentey
Dec 26, 2001·Chemical Reviews·K Müller-Dethlefs, P Hobza
May 30, 2002·Journal of the American Chemical Society·Matthew D LiptakGeorge C Shields
Mar 20, 2003·Angewandte Chemie·Emmanuel A MeyerFrançois Diederich
Dec 4, 2003·Journal of Computational Chemistry·Célia Fonseca GuerraF Matthias Bickelhaupt
May 19, 2004·Accounts of Chemical Research·Derek A PrattK U Ingold
Feb 1, 2007·Chemical Society Reviews·Scott L Cockroft, Christopher A Hunter
Dec 5, 2008·The Journal of Organic Chemistry·Pedro Jorge Silva
Apr 2, 2009·Angewandte Chemie·Tushar van der WijstBernhard Lippert
Feb 18, 2010·Journal of Chemical Theory and Computation·Steven E Wheeler, K N Houk
May 4, 2011·Angewandte Chemie·Laura M SalonenFrançois Diederich
Apr 17, 2014·Chemistry : a European Journal·Joan Simó PadialJasmin Mecinović
May 23, 2014·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Danijela Vojta, Mario Vazdar
Jan 10, 2013·ACS Medicinal Chemistry Letters·Carlos H Ríos Martínez, Christophe Dardonville
Jan 12, 2016·Wiley Interdisciplinary Reviews. Computational Molecular Science·Lando P Wolters, F Matthias Bickelhaupt
Aug 25, 2017·The Journal of Organic Chemistry·Joan Simó PadialJasmin Mecinović

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Citations

Apr 8, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Jie JianJasmin Mecinović
Jun 17, 2020·Angewandte Chemie·Rebecca J BurnsScott Lee Cockroft
Feb 29, 2020·Nature Chemistry·Mark JurratLiam T Ball
Dec 31, 2020·Chemistry : a European Journal·Jie JianJasmin Mecinović
Sep 30, 2020·Organic Letters·Jie JianJasmin Mecinović
Dec 28, 2021·Chemistry : a European Journal·Jie JianJasmin Mecinović

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