A Mechanistic Study on the Tautomerism of <i>H</i>-Phosphonates, <i>H</i>-Phosphinates and Secondary Phosphine Oxides
<i>H</i>-phosphonates, <i>H</i>-phosphinates and secondary phosphine oxides may be preligands, and are important building blocks in the synthesis of pharmaceuticals, pesticides, and <i>P</i>-ligands. The prototropic tautomerism influenced by substituent effects pl...
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| Format: | Article |
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MDPI AG
2019-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/21/3859 |
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| author | Daniella Vincze Péter Ábrányi-Balogh Péter Bagi György Keglevich |
| author_facet | Daniella Vincze Péter Ábrányi-Balogh Péter Bagi György Keglevich |
| author_sort | Daniella Vincze |
| collection | DOAJ |
| description | <i>H</i>-phosphonates, <i>H</i>-phosphinates and secondary phosphine oxides may be preligands, and are important building blocks in the synthesis of pharmaceuticals, pesticides, and <i>P</i>-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 <i>P</i>-molecules were elucidated for the mechanism of the interconversion. |
| first_indexed | 2024-12-10T09:38:27Z |
| format | Article |
| id | doaj.art-a253dbc577354f9bb8bbede4ed02dd5b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T09:38:27Z |
| publishDate | 2019-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a253dbc577354f9bb8bbede4ed02dd5b2022-12-22T01:54:06ZengMDPI AGMolecules1420-30492019-10-012421385910.3390/molecules24213859molecules24213859A Mechanistic Study on the Tautomerism of <i>H</i>-Phosphonates, <i>H</i>-Phosphinates and Secondary Phosphine OxidesDaniella Vincze0Péter Ábrányi-Balogh1Péter Bagi2György Keglevich3Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary<i>H</i>-phosphonates, <i>H</i>-phosphinates and secondary phosphine oxides may be preligands, and are important building blocks in the synthesis of pharmaceuticals, pesticides, and <i>P</i>-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 <i>P</i>-molecules were elucidated for the mechanism of the interconversion.https://www.mdpi.com/1420-3049/24/21/3859<i>h</i>-phosphonates<i>h</i>-phosphinatessecondary phosphine oxidestautomerismquantum chemical calculationsmechanism |
| spellingShingle | Daniella Vincze Péter Ábrányi-Balogh Péter Bagi György Keglevich A Mechanistic Study on the Tautomerism of <i>H</i>-Phosphonates, <i>H</i>-Phosphinates and Secondary Phosphine Oxides Molecules <i>h</i>-phosphonates <i>h</i>-phosphinates secondary phosphine oxides tautomerism quantum chemical calculations mechanism |
| title | A Mechanistic Study on the Tautomerism of <i>H</i>-Phosphonates, <i>H</i>-Phosphinates and Secondary Phosphine Oxides |
| title_full | A Mechanistic Study on the Tautomerism of <i>H</i>-Phosphonates, <i>H</i>-Phosphinates and Secondary Phosphine Oxides |
| title_fullStr | A Mechanistic Study on the Tautomerism of <i>H</i>-Phosphonates, <i>H</i>-Phosphinates and Secondary Phosphine Oxides |
| title_full_unstemmed | A Mechanistic Study on the Tautomerism of <i>H</i>-Phosphonates, <i>H</i>-Phosphinates and Secondary Phosphine Oxides |
| title_short | A Mechanistic Study on the Tautomerism of <i>H</i>-Phosphonates, <i>H</i>-Phosphinates and Secondary Phosphine Oxides |
| title_sort | mechanistic study on the tautomerism of i h i phosphonates i h i phosphinates and secondary phosphine oxides |
| topic | <i>h</i>-phosphonates <i>h</i>-phosphinates secondary phosphine oxides tautomerism quantum chemical calculations mechanism |
| url | https://www.mdpi.com/1420-3049/24/21/3859 |
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