Abstract: Most substituted benzoyl fluorides undergo hydrolysis in aqueous solution through an associative mechanism with p= 1.7, kHOH/kmD= 2.3 i 0.2, little dependence on the leaving group (kCl/kF= 1.2), and general-base catalysis by fluoride ion. There is an abrupt change to a dissociative mechanism through an acylium ion intermediate for the hydrolysis of p-(dimethy1amino) benzoyl and (in part) p-anisoyl fluorides, with p+ 5-1.2, kcl/kF= 106- ...
