ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 23, Number 1
JKCSEZ 23(1)
February 20, 1979 

The kinetics of the reaction of benzyl m-nitrobenzenesulfonate with m-and p-substituted N,N-dimethylanilines in acetone have been investigated by an electric conductivity method. The effects of substituents on the reactivity of N,N-dimethylaniline and the existence of linear free energy relationship were discussed. The rate constants k were in the range 2.55∼487 × 10-4l·mol-l·sec-1 (35℃) and increased with the electron donating ability of substituents. In the present reaction, the Hammett plot was correlated with σ substituent constant, especially using the new a value of 0.35 in p-MeO and it's ρ value was found to be -1.37. r value for the reaction was very large than the value obtained in the reaction of benzyl bromide. Bronsted linear relationship was shown between rate constant and basicites except for p-MeO resulted from solvent effect. From the Bronsted plot, this reaction was suggested that the cleavage of the C…O bond in the SN2 transition state proceed the bond formation.