Kinetic studies and thermodynamic treatments of substituent effect of the alkaline hydrolysis of acetoxybenzenes and acetoxynaphthalenes

ABSTRACT

The kinetics of the alkaline hydrolysis of acetoxybenzene, 1,4-diacetoxybenzene, l-acetoxynaphthalene, 1,4-diacetoxynaphthalene and 1,5-diacetoxynaphthalene have been studied in 50% [v/v] dioxane-water. Analysis of the data showed that an increase in the rate was found to be dependent on the position of the acetoxy group. Also, the presence of oxo-group caused an inhibition in the rate to a great extent either in the naphthalene or benzene compounds. The various thermodynamic parameters were deduced. A linear free energy relationship was observed for such substituted acetoxynaphthalene where a good correlation between log k vs. deltaij was observed. Also, the effect of bromo-substitution on the rate of hydrolysis of 2-acetoxynanphthalene has been studied