Mechanistic insights into the amidolysis of a phosphate triester: the antagonistic role of water.
Amanda K JacobsLeociley R A MenezesJuliano M FernandesGuilherme L KosteczkaGuilherme L SassakiRenan B CamposPublished in: Organic & biomolecular chemistry (2022)
The breakdown of O , O -diethyl-2,4-dinitrophenyl phosphate in formamide (FMD) solutions is assessed using kinetic studies and 31 P nuclear magnetic resonance (NMR) analysis. Regiospecific nucleophilic amidolysis via P-O bond cleavage is observed, leading to non-toxic diester and FMD regeneration. In the systems evaluated, water plays an antagonistic role: while it is key for the breakdown of the reaction intermediate, it inhibits the nucleophilic activity of FMD by hydrogen bonding effects.