Zhang, Xian Man published the artcileEquilibrium acidities and homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in N-substituted trimethylammonium and pyridinium cations, Related Products of pyridine-derivatives, the publication is Journal of Organic Chemistry (1993), 58(11), 3060-6, database is CAplus.
Equilibrium acidities (pKHA) of the cations in 16 N-substituted trimethylammonium salts, one N-phenacylquinuclidinium salt, 8 N-substituted pyridinium salts, and N-(ethoxycarbonyl)isoquinolinium bromide, together with the oxidation potentials of their conjugate bases, have been determined in Me2SO. The acidifying effects of the α-trimethylammonium groups (α-Me3N+) and the α-pyridinium groups (α-PyN+) on the adjacent acidic C-H bonds in these cations were found to average about 10 and 18 pKHA units, resp. The homolytic bond dissociation energies of the acidic C-H bonds in these cations, estimated by the combination of the equilibrium acidities with the oxidation potentials of their corresponding conjugate bases (ylides), show that the α-trimethylammonium groups destabilize adjacent radicals by 2-6 kcal/mol, whereas α-pyridinium groups stabilize adjacent radicals by 3-6 kcal/mol. The effects of α-pyridinium groups on the stabilization energies of the radicals derived from these cations were ca. 4-10 kcal/mol smaller than those of the corresponding Ph groups, whereas their effects on the equilibrium acidities of the cations were 5.4-13.1 pKHA units larger. The pKHA value of tetramethylammonium cation (Me4N+) was estimated by extrapolation to be about 42 in Me2SO.
Journal of Organic Chemistry published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C8H11BO3, Related Products of pyridine-derivatives.
Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem