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

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

doi:10.1021/acs.joc.8b03147

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

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Research output: Contribution to Journal › Article › Academic › peer-review

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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.

Original language	English
Pages (from-to)	3632-3637
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	84
Issue number	6
Early online date	22 Feb 2019
DOIs	https://doi.org/10.1021/acs.joc.8b03147
Publication status	Published - 15 Mar 2019

Funding

We thank The Netherlands Organization for Scientific Research (NWO) for financial support. J.P. thanks the Spanish MINECO (CTQ2016-77558-R and MDM-2017-0767) and the Generalitat de Catalunya (2017SGR348) for support.

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10.1021/acs.joc.8b03147

Probing Through-Space Polar-π Interactions in 2,6-DiarylphenolsFinal published version, 1.62 MBLicence: Article 25fa Dutch Copyright Act

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AU - Bosmans, Vera

AU - Poater, Jordi

AU - Hammink, Roel

AU - Tinnemans, Paul

AU - Bickelhaupt, F. Matthias

AU - Mecinović, Jasmin

PY - 2019/3/15

Y1 - 2019/3/15

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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.

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

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CCDC 1882991: Experimental Crystal Structure Determination

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

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CCDC 1882991: Experimental Crystal Structure Determination

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