The alkaline hydrolysis of ethyl 1-naphthoate, ethyl 3-methyl-1-naphthoate and ethyl 4-methyl-1-naphthoate in ethanol-water (1956)
AuthorsPacker, J. E.show all
3-Methyl-1-naphthoic acid, a compound not previously known, has been prepared. The kinetics of the alkaline hydrolysis of ethyl 1-naphthoate, ethyl 3-methyl-1-naphthoate, and ethyl 4-methyl-1-naphthoate in ethanol-water (85:15 by weight), have been studied at four temperatures, using a titration method; Arrhenius frequency factors and energies of activation have been determined. These values for ethyl 1-naphthoate were found to differ from those of a previous investigator, and the differences have been discussed. Relative free energies, heats, and entropies of activation for the alkaline hydrolysis of ethyl 3-methyl-, 4-methyl-, 2-nitro-, 3-nitro-, 4-nitro-, 5-nitro-, 6-nitro-, 8-nitro-, and 4:5-dinitro-1-naphthoates have been evaluated and their significance has been discussed. Hammett substituent constants for the methyl group in the 3- and 4- positions and for the nitro group in the 3-, 4-, 5- and 6- positions have been calculated.