Abstract
Using a quadrupole ion trap mass spectrometer, trimethyl borate was allowed to react with dihydrogen phosphate, deprotonated O-phosphoserine, and a set of hydrogen bonded complexes involving dihydrogen phosphate and neutral acids (phosphoric acid, acetic acid, serine, and O-phosphoserine). The reactions show a consistent pattern in which the initial attack leads to addition with the loss of one or two CH3OH molecules. Collision-activated dissociation (CAD) experiments on the reaction products generally lead to the loss of an additional CH3OH molecule. In no case is a partner from the original hydrogen-bonded complex lost. The results indicate that the reactions lead to structures where the phosphate and its complex partner are covalently bound to the boron. For each of the reactions, rate constants were determined. In the course of CAD experiments (up to MS5), several novel borophosphate structures were identified. The work is supported by ab initio calculations on selected species.
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Dedicated to Professor Charles H. DePuy on the occasion of his 75th birthday and in honor of his 2002 James Flack Norris Award in Physical Organic Chemistry.
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Gronert, S., O’Hair, R.A.J. Gas phase reactions of trimethyl borate with phosphates and their non-covalent complexes. J. Am. Soc. Spectrom. 13, 1088–1098 (2002). https://doi.org/10.1016/S1044-0305(02)00424-5
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DOI: https://doi.org/10.1016/S1044-0305(02)00424-5