Theoretical investigation on the tautomerization mechanism of phosphinic acids

Abstract

H-phosphonates, H-phosphinates and secondary phosphine oxides (SPO) are essential compounds for the synthesis of pharmaceuticals, herbicides, pesticides, and phosphine ligands. Notably, prototropic tautomerism and substituent effects play an important role in the reactivity of the above compounds.^[1] The main goal of our research was to study the tautomerism of symmetrical and asymmetrical phosphinic acids, by the means of computational investigation, applying several DFT and ab initio methods. We have investigated the effect of substituents, implicit solvents and also multiple kinetic pathways were elucidated for the possible tautomerization mechanism, including intramolecular, and various intermolecular routes.

Graphical Abstract

Keywords:

• H-phosphonates
• H-phosphinates
• secondary phosphine oxides
• tautomerization
• computational investigation

Additional information

Funding

Péter Ábrányi-Balogh is grateful for the support of the Ministry of Human Capacities (Scolarship for Young Talents, NTP-NFTÖ-18-B-0018).