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

Radboud University Nijmegen
ICREA
University of Barcelona
Vrije Universiteit Amsterdam
University of Southern Denmark

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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
DOIs	https://doi.org/10.1021/acs.joc.8b03147
Publication status	Published - 15 Mar 2019
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.8b03147

Cite this

@article{6f3aa81bc0af46d8b8842851f1c6ffd8,

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

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.",

author = "Vera Bosmans and Jordi Poater and Roel Hammink and Paul Tinnemans and Bickelhaupt, \{F. Matthias\} and Jasmin Mecinovi{\'c}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = mar,

day = "15",

doi = "10.1021/acs.joc.8b03147",

language = "English",

volume = "84",

pages = "3632--3637",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "6",

}

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

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 -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this