Catalytic Cleavage of Active Phosphate and Ester Substrates by Iodoso- and Iodoxybenzoates

Article abstract of DOI:10.1021/ja00321a027

p-Nitrophenyl acetate, p-nitrophenyl hexanoate, and p-nitrophenyl diphenyl phosphate (PNPDPP) were cleaved by o-iodosobenzoate, o-iodoxybenzoate, and 5-(n-octyloxy)-2-iodosobenzoate (3) in aqueous micellar cetyltrimethylammonium chloride solutions at pH 8.The system 3/CTACl was the best catalyst and PNPDPP was the most reactive substrate.In a remarkably rapid hydrolytic reaction at 25 deg C, 1.0*10^-5 M PNPDPP was cleaved by 7.14*10^-5 M 3 in 2.0*10^-4 M CTACl with k_φ=1.04 s^-1.Experiments in which > <3> demonstrated that the catalyst "turned over"; i.e., degradation of an intermediate phosphate was not rate limiting.