Theoretical Study of the Reaction of Formation of Some Free Phosphines by Stereoselective Hydrophosphination through DFT Method
Kouadio Valery Bohoussou
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, Côte-d’Ivoire
Anoubilé Bénié
Laboratoire de Chimie Bio-Organique et de Substances Naturelles, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, Côte-d’Ivoire
Mamadou Guy-Richard Koné *
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, Côte-d’Ivoire
N’guessan Yao Silvère Diki
Laboratoire de Chimie Physique, Université Félix Houphouët- Boigny Abidjan-Cocody, 22 BP 582 Abidjan 22, Côte-d’Ivoire
Kafoumba Bamba
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, Côte-d’Ivoire
Nahossé Ziao
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, Côte-d’Ivoire
*Author to whom correspondence should be addressed.
Abstract
In this work the formation of vinylphosphines was studied through the hydrophosphination reaction. The study aims to rationalize the stereoselectivity of these compounds using quantum DFT methods. This theoretical study of chemical reactivity was conducted at B3LYP/6-311 + G (d, p) level. Global chemical reactivity descriptors, stationary point energies and activation barriers were examined to foretell the relative stability of the stereoisomers formed. The various results obtained have revealed that the addition of arylphosphine to dihalogenoacetylene is stereospecific. The Trans form of vinylphosphines is more stable than the Cis form, when the substituent on phosphorus generates less or no π-conjugations. On the other hand, the Cis isomer is predominant when the aryl radical favors more π-conjugations. The theoretical results obtained are in agreement with the experimental results.
Keywords: Hydrophosphination, free phosphine, global descriptors, transition state, stationary point energies