Solvent effect on the kinetics of the reaction of 2,3-[9,10-dihydroanthracene-endo-9,10-diyl]-N-(2,4-dinitrophenoxy)succinimide with piperidine

Abstract

The kinetics of the reaction between 2,3-(9,10-dihydroanthracene-endo-9,10-diyl)-N-(2,4-dinitrophenoxy)succinimide and piperidine have been studied in acetonitrile, ethyl acetate, benzene, dioxane, and methanol at 35 ± 0.1 °C. The second-order rate coefficient increases with increased piperidine concentration in all cases except for methanol. The observed base catalysis in acetonitrile, ethyl acetate, benzene and dioxane is explained in terms of the rate-limiting nucleofuge detachment. For the case of methanol, due to its high hydrogen-bond donating property, the formation of the intermediate is rate determining.