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

Joan Simõ Padial; René de Gelder; Célia Fonseca Guerra; F. Matthias Bickelhaupt; Jasmin Mecinović

doi:10.1002/chem.201304462

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

Joan Simõ Padial
, René de Gelder
, Célia Fonseca Guerra
, F. Matthias Bickelhaupt
, Jasmin Mecinović^*

^*Kontaktforfatter

Radboud University Nijmegen
Vrije University Amsterdam

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Abstract

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

Originalsprog	Engelsk
Tidsskrift	Chemistry - A European Journal
Vol/bind	20
Udgave nummer	21
Sider (fra-til)	6268-6271
Antal sider	4
ISSN	1521-3765
DOI	https://doi.org/10.1002/chem.201304462
Status	Udgivet - 19. maj 2014
Udgivet eksternt	Ja

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10.1002/chem.201304462

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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 pKa values. Hammett analysis illustrates that the basicity of pyridines correlates well with the sigma values of the substituents at the para position of the flanking aryl rings.",

keywords = "basicity, Hammett analysis, non-covalent interactions, polar-π interactions, pyridines, Thermodynamics, Proteins/chemistry, Amino Acids, Aromatic/chemistry, Models, Molecular, Protein Conformation, Protein Folding, Pyridinium Compounds/chemistry",

author = "Padial, \{Joan Sim{\~o}\} and \{de Gelder\}, Ren{\'e} and \{Fonseca Guerra\}, C{\'e}lia and Bickelhaupt, \{F. Matthias\} and Jasmin Mecinovi{\'c}",

year = "2014",

month = may,

day = "19",

doi = "10.1002/chem.201304462",

language = "English",

volume = "20",

pages = "6268--6271",

journal = "Chemistry - A European Journal",

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TY - JOUR

T1 - Stabilisation of 2,6-diarylpyridinium cation by through-space polar-π interactions

AU - Padial, Joan Simõ

AU - de Gelder, René

AU - Fonseca Guerra, Célia

AU - Bickelhaupt, F. Matthias

AU - Mecinović, Jasmin

PY - 2014/5/19

Y1 - 2014/5/19

N2 - The through-space polar-π interactions between pyridinium ion and the adjacent aromatic rings in 2,6-diarylpyridines affect the pKa values. Hammett analysis illustrates that the basicity of pyridines correlates well with the sigma values of the substituents at the para position of the flanking aryl rings.

AB - The through-space polar-π interactions between pyridinium ion and the adjacent aromatic rings in 2,6-diarylpyridines affect the pKa values. Hammett analysis illustrates that the basicity of pyridines correlates well with the sigma values of the substituents at the para position of the flanking aryl rings.

KW - basicity

KW - Hammett analysis

KW - non-covalent interactions

KW - polar-π interactions

KW - pyridines

KW - Thermodynamics

KW - Proteins/chemistry

KW - Amino Acids, Aromatic/chemistry

KW - Models, Molecular

KW - Protein Conformation

KW - Protein Folding

KW - Pyridinium Compounds/chemistry

UR - https://www.scopus.com/pages/publications/84900805599

U2 - 10.1002/chem.201304462

DO - 10.1002/chem.201304462

M3 - Journal article

C2 - 24737605

SN - 1521-3765

VL - 20

SP - 6268

EP - 6271

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

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