Covalent hydration of nitrobenzofuroxans compounds: Kinetic and theoretical study using reactivity-selectivity descriptor

摘要

A kinetic study of the covalent hydration of a series of nitrobenzofuroxans, to give the corresponding hydroxy cr-adduct, in aqueous solution is reported. Analysis of the data obtained in the pH range 0.8-13 has allowed dissection of the observed rates into forward (k1~(H2O). k2~(OH-)) and reverse (K_(-1)~(H+), K_(-2)) rate constants as well as the obtention of pKa values for H2O addition to the carbocyclic ring. Global and local DFT-based reactivity descriptors are used to rationalize the trends observed in reaction rate constants and to explain the main reaction product experimentally. The reactivity-selectivity dual descriptor has been used to characterize the regio-selectivity that might be driving the covalent hydration reactions.