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. 2022 Mar 23;20(12):2462-2466.
doi: 10.1039/d2ob00180b.

Mechanistic insights into the amidolysis of a phosphate triester: the antagonistic role of water

Amanda K Jacobs  1 , Leociley R A Menezes  2 , Juliano M Fernandes  1 , Guilherme L Kosteczka  1 , Guilherme L Sassaki  2 , Renan B Campos  1
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Mechanistic insights into the amidolysis of a phosphate triester: the antagonistic role of water

Amanda K Jacobs et al. Org Biomol Chem. .

Abstract

The breakdown of O,O-diethyl-2,4-dinitrophenyl phosphate in formamide (FMD) solutions is assessed using kinetic studies and 31P 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.

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