4.6 Article

Stabilisation of 2,6-Diarylpyridinium Cation by Through- Space Polar- p Interactions

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 21, Pages 6268-6271

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304462

Keywords

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

Funding

  1. Radboud University Nijmegen
  2. Netherlands Organization for Scientific Research (NWO-CW)
  3. National Research School Combination Catalysis (NRSC-C)

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The through-space polar- interactions between pyridinium ion and the adjacent aromatic rings in 2,6-diarylpyridines affect the pK(a)values. 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.

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