Catalysis of hydrolysis of a schiff base by a carboxyl-containing poly(ethylenimine) derivative

Hydrolysis of 3-methyl-2-cyclohexenylidene laurylamine (I) in the presence and absence of laurylsuccinoylpoly(ethylenimine) has been studied. Water attack on the conjugate acid of I in the polymer environment is about 10² times faster than in bulk medium. To achieve the same rate in bulk media by general base catalysis, about 70 M acetate or cacodylate would be needed. This indicates that the reactivity of the carboxylate attached to the polymer is substantially enhanced by the polymer environment.