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.
authors.affiliation: Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3393.
authors.forename: Joan Simó
authors.initials: JS
authors.lastname: Padial
authors.forename: René
authors.initials: R
authors.lastname: de Gelder
authors.forename: Célia
authors.initials: C
authors.lastname: Fonseca Guerra
authors.forename: F Matthias
authors.initials: FM
authors.lastname: Bickelhaupt
authors.forename: Jasmin
authors.initials: J
authors.lastname: Mecinović
mesh_terms: D024322:Amino Acids, Aromatic / Q000737:chemistry*; D008958:Models, Molecular; D011487:Protein Conformation; D017510:Protein Folding; D011506:Proteins / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D024322:Amino Acids, Aromatic; D011506:Proteins; D011726:Pyridinium Compounds
keywords: Hammett analysis; basicity; non-covalent interactions; polar-π interactions; pyridines