Metal-hydroxide promoted hydrolysis of activated esters. Hydrolysis of 2,4-dinitrophenyl acetate and 4-nitrophenyl acetate

Abstract

A range of exchange-labile and non-labile metal-hydroxide species readily promote the hydrolyses of 2,4-dinitrophenyl acetate and 4-nitrophenyl acetate. Kinetic studies (25ºC, I 1.0 mol dm^-3 NaClO₄) show that these processes follow shallow Bronsted slopes (β 0.33 and 0.40 respectively) which extend over a range of 10¹⁰ in nucelophile basicity. A correlation is reported which allows the prediction of reaction rates between [CO(NH₃)₅OH]²⁺ and other activated charge-neutral carbonyl compounds.