Kinetics of the reaction of 2-chloro-3,5-dinitro-pyridine with aniline in hydroxylic solvents

ABSTRACT

The rates of aromatic nucleophilic substitution [ANS] reactions are notably affected by the solvent polarity such as substrate or intermediate[s] solvent interactions[1-3], the non-specific coulombic, inductive and dispersion interactions, specific hydrogen bond, electron pair donor [EPD], electron pair acceptor [EPA] and solvophobic interactions[4]. It has been found that the reaction of nitroaryl halides with amines in hydroxylic solvents was inversely proportional to the hydrogen bond donating [HBD] ability of the solvent[5]. Moreover, the reaction rate in these hydroxylic solvents was found to be smaller than that in aprotic solvents, which suggests that inter-and intramolecular bond interactions, in the pure solvent and between the solvent and the amine, are relevant in determining the reaction rates[6]. The object of this work was to supplement a systematic study of the hydroxylic solvents influence on the reaction rate of 2-chloro-3,5-dinitropyridine with aniline as a simple model in heterocyclic rings of the ANS [Aromatic nucleophulic substitution] reaction. Also, it is of interest to correlate the kinetic data with E[T[30]] values on rates the preferential solvation in order to evaluate its influence