The influence of the nitro-group upon side-chain reactivity. Part III. The influence of steric and mesomeric interaction factors on the rates of alkaline hydrolysis of ethyl nitrobenzoates

Abstract

While a nitro-group in the 4-position increases the rate of alkaline hydrolysis of ethyl benzoate in 80% v/v aqueous ethanol at 35°ca. 120 times, it increases it only ca. 7 times when in the 2-position. A methoxyl group in the 3- or 5-position in ethyl 2- or 4-nitrobenzoate affects the rates considerably according to steric or mesomeric interactions in these systems. A 3-O^– substituent strongly decreases the rate of hydrolysis of ethyl 4-nitrobenzoate, owing to mesomeric interaction between the 4-NO₂ and the 3-O^– substituents. Ultraviolet spectra of the esters throw some light on the results.