Kinetic Studies of Acenaphthene Oxidation Catalyzed by N‐Hydroxyphthalimide

ABSTRACT The acenaphthene oxidation with molecular oxygen in the presence of N ‐hydroxyphthalimide (NHPI) has been investigated. It is shown that the main oxidation product is acenaphthene hydroperoxide. The phthalimide‐ N ‐oxyl (PINO) radical has been generated in situ from its hydroxyimide parent, NHPI, by oxidation with iodobenzenediacetate. The rate constant of H‐abstraction ( k H ) from acenaphthene by PINO has been determined spectroscopically in acetonitrile. The kinetic isotope effect and the activation parameters have also been measured. On the basis of the results of our studies and available published literature data, a plausible mechanism for the oxidation process of acenaphthene with dioxygen catalyzed by NHPI was discussed.