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Stabilisation of 2,6‐Diarylpyridinium Cation by Through‐Space Polar–π Interactions
Author(s) -
Padial Joan Simó,
de Gelder René,
Fonseca Guerra Célia,
Bickelhaupt F. Matthias,
Mecinović Jasmin
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304462
Subject(s) - pyridinium , polar , aryl , chemistry , space (punctuation) , ion , aromaticity , sigma , stereochemistry , medicinal chemistry , physics , organic chemistry , alkyl , molecule , quantum mechanics , linguistics , philosophy
The through‐space polar–π interactions between pyridinium ion and the adjacent aromatic rings in 2,6‐diarylpyridines affect the p K a 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.