Stabilisation of 2, 6‐Diarylpyridinium Cation by Through‐Space Polar–π Interactions. Issue 21 (15th April 2014)

• Record Type: Journal Article
• Authors: Padial, Joan Simó; de Gelder, René; Fonseca Guerra, Célia; Bickelhaupt, F. Matthias; Mecinović, Jasmin
• Is Part Of: Chemistry. Volume 20:Issue 21(2014)
• Page Start: 6268
• Page End: 6271
• Publication Date: 2014-04-15
• Subjects: basicity -- Hammett analysis -- non‐covalent interactions -- polar–π interactions -- pyridines; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201304462
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : 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 (see figure).