Proton, carbon-13, and fluorine-19 NMR study of N-arylpyridinium salts: Attempted calculations of the σ1 and σR0 values for N-pyridinium substituents

Abstract

The synthesis and NMR study of fourteen N-arylpyridinium salts have been done. Chemical shifts and coupling constants (1H-1H, 1H-13C, 1H-19F, and 13C-19F) have been measured in hexadeuteriodimethyl sulphoxide. Conformation about the phenylpyridinium bond is discussed. The electronic properties of the three pyridinium substituents ( pyridinium, 2,4,6-trimethylpyridinium, and 2,4,6-triphenylpyridinium) have been determined (Hammet and Taft's σ values) and compared with those of the trimethylammonium substituent.