Issue 12, 2022

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Jan 2022
Accepted
18 Feb 2022
First published
24 Feb 2022

Org. Biomol. Chem., 2022,20, 2462-2466

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

A. K. Jacobs, L. R. A. Menezes, J. M. Fernandes, G. L. Kosteczka, G. L. Sassaki and R. B. Campos, Org. Biomol. Chem., 2022, 20, 2462 DOI: 10.1039/D2OB00180B

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