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Open AccessArticle

A Mechanistic Study on the Tautomerism of H-Phosphonates, H-Phosphinates and Secondary Phosphine Oxides

1
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
2
Research Centre for Natural Sciences, Medicinal Chemistry Research Group, 1117 Budapest, Hungary
*
Authors to whom correspondence should be addressed.
Academic Editor: Maxim L. Kuznetsov
Molecules 2019, 24(21), 3859; https://doi.org/10.3390/molecules24213859
Received: 3 October 2019 / Revised: 22 October 2019 / Accepted: 23 October 2019 / Published: 25 October 2019
(This article belongs to the Special Issue Theoretical Investigations of Reaction Mechanisms)
H-phosphonates, H-phosphinates and secondary phosphine oxides may be preligands, and are important building blocks in the synthesis of pharmaceuticals, pesticides, and P-ligands. The prototropic tautomerism influenced by substituent effects plays an important role in the reactivity of these species. The main goal of our research was to study the tautomerism of the >P(O)H reagents by means of computational investigations applying several DFT methods at different levels. We focused on the effect of implicit solvents, and on explaining the observed trends with physical chemical molecular descriptors. In addition, multiple reaction pathways incorporating three P-molecules were elucidated for the mechanism of the interconversion. View Full-Text
Keywords: H-phosphonates; H-phosphinates; secondary phosphine oxides; tautomerism; quantum chemical calculations; mechanism H-phosphonates; H-phosphinates; secondary phosphine oxides; tautomerism; quantum chemical calculations; mechanism
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MDPI and ACS Style

Vincze, D.; Ábrányi-Balogh, P.; Bagi, P.; Keglevich, G. A Mechanistic Study on the Tautomerism of H-Phosphonates, H-Phosphinates and Secondary Phosphine Oxides. Molecules 2019, 24, 3859.

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