112391-40-9Relevant articles and documents
Substituted o-Iodoso- and o-Iodoxybenzoic Acids: Synthesis and Catalytic Activity in the Hydrolysis of Active Phosphorus Esters and Related Systems
Katritzky, Alan R.,Duell, Bradley L.,Durst, H. Dupont,Knier, Barry L.
, p. 3972 - 3978 (2007/10/02)
2-Iodoso- and 2-iodoxybenzoic acids containing alkyl, alkyloxy, nitro, carboxyl, and water-solubilizing substituents have been synthesized, and their influence on the rates of hydrolysis of p-nitrophenyl diphenyl phosphate (PNPDPP), p-nitrophenyl isopropylphenylphosphinate (NPIPP), and p-nitrophenyl hexanoate (PNPH) has been determined in the presence of added cetyltrimethylammonium chloride (CTAC).All the compounds are true catalysts, with rates increasing with increasing catalyst concentration. 2-Iodoxybenzoic acids possess 60-110percent of the activity of their 2-iodosobenzoic acid analogues in 0.001 M CTAC.The effects of substituents of variable electronic and aqua/lipophilic character upon catalytic activity have been determined.Lipophilic substituents significantly enhanced the rates while simple ring substitution with electron-releasing and -withdrawing and water-soluble groups had only moderate effects.Extraordinary rate enhancements were obtained with 5-(2-hydroxyethoxy)-2-iodoxybenzoic acid and 5-(alkyloxy)-2-iodosobenzoic acid and -2-iodoxybenzoic acid derivatives, giving second-order rate constants of 400-5000 M-1 s-1.The efficient catalysis of the hydrolysis of active phosphorus derivatives renders these aromatic 2-iodoso- and 2-iodoxybenzoic acids potentially useful decontaminants.
Catalytic Cleavage of Active Phosphate and Ester Substrates by Iodoso- and Iodoxybenzoates
Moss, Robert A.,Alwis, K. W.,Shin, Jae-Sup
, p. 2651 - 2655 (2007/10/02)
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 kφ=1.04 s-1.Experiments in which > demonstrated that the catalyst "turned over"; i.e., degradation of an intermediate phosphate was not rate limiting.