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Detection of metaphosphate intermediates in reaction solutions of phosphate esters: Chromatographic and spectroscopic studies

GRAPHICAL ABSTRACT ABSTRACT This study was undertaken to gain a better understanding of uncatalysed phosphoryl transfer reactions under neutral pH conditions in aqueous media. A combination of chromatographic (Ultra high performance liquid chromatography, UHPLC) and spectroscopic (Quadrupole time-of-flight-mass spectrometry- qTOF-MS;) UV-vis; and FTIR techniques were utilized to probe the mechanism of reaction under physiological conditions (aqueous medium; pH 7.0; 25°C). Mass spectroscopic data from these studies reveal that the phosphate monoesters, phenyl phosphate (PP) and 4-nitrophenyl phosphate (NPP) undergo collision-induced dissociation dynamics through the formation of the metaphosphate intermediate, [PO3]− – m/z 79, a process that was found to be independent of the pKa of the leaving group. Under conditions of the present experiment, the metaphosphate intermediate does not undergo protonation to either metaphosphoric acid, HPO3 or the dibasic phosphonic acid, H3PO3.