Reactivity of acetanilides in the alkaline hydrolysis reaction: theory vs. experiment

摘要

The rate constants (at 25 degrees C) for the alkaline hydrolysis of a series of seven acetanilide derivatives were determined experimentally. The series included the parent compound acetanilide and the following para-substituents: CH3, OCH3, NH2, CHO, COCH3 and NO2. The obtained kinetic data were then correlated with the following theoretically estimated reactivity indices: Mulliken and NBO atomic charges, the Parr electrophilicity index (omega), and the electrostatic potential at the carbon and nitrogen atoms of the reaction center (V-C, V-N). Very good correlation between the logarithm of the rate constant, ln k, and the omega values was established. Excellent correlations between V-C and V-N and ln k were found. The data obtained show that the model-independent electrostatic potential at the nuclei provides a reliable quantitative approach for describing the reactivity of organic compounds.