A. Shunmugasundaram et al., KINETICS OF ADDITION OF N-BUTYLAMINE TO 4'-SUBSTITUTED N-METHYL-2-STRYLPYRIDINIUM IODIDES, Indian journal of chemistry. Sect. A: Inorganic, physical, theoretical & analytical, 33(5), 1994, pp. 417-419
The kinetics of addition of n-butylamine to 4'-substituted N-methyl-2-
styrylpyridinium iodides in acetonitrile have been followed spectropho
tometrically. The reaction is first order with respect to the substrat
e and the order in n-butylamine is non-integral. A mechanism involving
the formation of the zwitterionic addition complex in the first equil
ibrium step with subsequent proton transfer in a slow step is proposed
. Structure-reactivity study with various 4'-substituents shows that t
he rate of proton transfer is accelerated by electron-releasing substi
tuents and retarded by electron-withdrawing substituents.