Kinetics of the nucleophilic substitution reactions of methyl 2,4-dichloro-3,5-dinitrobenzoate with piperidine, piperazine, morpholine and thiomorpholine in methanol and benzene

The kinetic of the nucleophilic substitution of methyl 2,4-dichloro-3,5-dinitrobenzoate with piperidine, piperazine, morpholine and thiomorpholine in methanol and benzene were determined spectrophotometrically at different amine concentrations and at temperatures ranging from 25 to 45 degrees C. The second order rate constants and the thermodynamic parameters show that the reactions are not amine catalysed and are greatly dependent of the nature of solvent and amine. UV, IR, H-1 NMR, and elemental analysis are used to prove the aminodechlorination at C-2.