Proton Inventory of Phthalic Anhydride Hydrolysis. Comments on Analysis of Proton-Inventory Data

Article abstract of DOI:10.1021/jo01298a001

The spontaneous hydrolysis of phthalic anhydride exhibits rate constants k_n in mixtures of deuterium oxide (atom fraction n of deuterium) and protium oxide which are best described by the equation 10⁶k_n = 1058(1 - n + 0.69)³(1 - n + 1.33n) s^-1.This result suggests a hydronium ion and a gem-diol-like proton as structural features in the rate-limiting transition-state structure.Two such structures, 3 and 4, are proposed as consistent with this result and previous mechanistic studies.A thorough analysis of nonlinear equations used in proton inventory studies is presented and the criteria for evaluating a "good fit" are discussed.