Stabilisation of 2,6-diarylpyridinium cation by through-space polar-π interactions

Joan Simõ Padial; René Degelder; Célia Fonsecaguerra; F. Matthias Bickelhaupt; Jasmin Mecinovic̈

doi:10.1002/chem.201304462

Stabilisation of 2,6-diarylpyridinium cation by through-space polar-π interactions

Joan Simõ Padial
, René Degelder
, Célia Fonsecaguerra
, F. Matthias Bickelhaupt
, Jasmin Mecinovic̈

Radboud University Nijmegen
Vrije Universiteit Amsterdam

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

18 Citations (Scopus)

Abstract

The through-space polar-π interactions between pyridinium ion and the adjacent aromatic rings in 2,6-diarylpyridines affect the pK_avalues. Hammett analysis illustrates that the basicity of pyridines correlates well with the sigma values of the substituents at the paraposition of the flanking aryl rings. The through-space polar-π interactions between pyridinium ion and the adjacent aromatic rings in 2,6-diarylpyridines affect the pK_avalues. Hammett analysis illustrates that the basicity of pyridines correlates well with the sigma values of the substituents at the paraposition of the flanking aryl rings (see figure).

Original language	English
Pages (from-to)	6268-6271
Number of pages	4
Journal	Chemistry - A European Journal
Volume	20
Issue number	21
DOIs	https://doi.org/10.1002/chem.201304462
Publication status	Published - 19 May 2014
Externally published	Yes

Keywords

basicity
Hammett analysis
non-covalent interactions
polar-π interactions
pyridines

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201304462

Cite this

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title = "Stabilisation of 2,6-diarylpyridinium cation by through-space polar-π interactions",

abstract = "The through-space polar-π interactions between pyridinium ion and the adjacent aromatic rings in 2,6-diarylpyridines affect the pKavalues. Hammett analysis illustrates that the basicity of pyridines correlates well with the sigma values of the substituents at the paraposition of the flanking aryl rings. The through-space polar-π interactions between pyridinium ion and the adjacent aromatic rings in 2,6-diarylpyridines affect the pKavalues. Hammett analysis illustrates that the basicity of pyridines correlates well with the sigma values of the substituents at the paraposition of the flanking aryl rings (see figure).",

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AU - Padial, Joan Simõ

AU - Degelder, René

AU - Fonsecaguerra, Célia

AU - Bickelhaupt, F. Matthias

AU - Mecinovic̈, Jasmin

PY - 2014/5/19

Y1 - 2014/5/19

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KW - basicity

KW - Hammett analysis

KW - non-covalent interactions

KW - polar-π interactions

KW - pyridines

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 21

ER -

Stabilisation of 2,6-diarylpyridinium cation by through-space polar-π interactions

Abstract

Keywords

ASJC Scopus subject areas

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