Quantum Chemical Characterization of Hydrogen Bonding Sites in Three 4-(4-Halo-Phenyl)-6-(Furan-2-yl) Pyrimidin-2-Amine Derivatives

Traoré, Yafigui; Bamba, Kafoumba; Ziao, Nahossé; Affi, Sopi Thomas; Koné, Mamadou Guy-Richard

doi:10.4236/cc.2017.53008

Cited by 3 publications

(1 citation statement)

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“…Its efficiency and accuracy in the evaluation of a number of molecular properties [10] have been recognized by all. Moreover, the examination and proper exploitation of frontier orbital energies (SOMO) guided the understanding of the chemical reactivity of free and complexed phosphines by Lee et al by manipulating the electronic density as a fundamental quantity [11][12][13]. This work is part of the design and synthesis of new series of phosphine-based organic semiconductors.…”

Section: Introductionmentioning

confidence: 99%

Contribution to Reactivity, Stability and Selectivity of Monodentated Free Phosphines

Bohoussou¹,

Bénié²,

Koné³

et al. 2019

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Phosphines having a high degree of instability in their syntheses, it is necessary to find conditions for obtaining stable products in order to propose new stable and active compounds. It is this concern that responds to the theoretical study of stability and selectivity. This theoretical study of chemical reactivity was carried out using the Density Functional Theory (DFT) method, at the B3LYP/6-31G (p) calculation level. The use of the Frontier Molecular Orbital (FMO) theory, with the Single Orbital Molecular Orbital (SOMO) cation model, made it possible to study the stability of some isomers formed during the addition of free phosphines to the carbon-carbon triple bond. The analysis of these reactivity quantities allowed us to conclude that the presence of halogens on acetylene influences the stability of the stereoisomers during their formation. This stability increases as the electronegativity of the halogen decreases. The large number of π conjugation favors the formation of Cis isomers and the lack or small amount of π conjugation orients the formation of Trans isomers. The nature of the aryl substituent and the number of low electronegativity halogen on the phosphine are capable of promoting the production of stable products.

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Section: Introductionmentioning

confidence: 99%

Contribution to Reactivity, Stability and Selectivity of Monodentated Free Phosphines

Bohoussou¹,

Bénié²,

Koné³

et al. 2019

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Synthesis, spectral characterization, docking studies and biological activity of urea, thiourea, sulfonamide and carbamate derivatives of imatinib intermediate

et al. 2018

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Theoretical Study of the Reaction of Formation of Some Free Phosphines by Stereoselective Hydrophosphination through DFT Method

Bohoussou

Bénié

Koné

et al. 2018

AJACR

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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.

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Quantum Chemical Characterization of Hydrogen Bonding Sites in Three 4-(4-Halo-Phenyl)-6-(Furan-2-yl) Pyrimidin-2-Amine Derivatives

Cited by 3 publications

References 24 publications

Contribution to Reactivity, Stability and Selectivity of Monodentated Free Phosphines

Contribution to Reactivity, Stability and Selectivity of Monodentated Free Phosphines

Synthesis, spectral characterization, docking studies and biological activity of urea, thiourea, sulfonamide and carbamate derivatives of imatinib intermediate

Theoretical Study of the Reaction of Formation of Some Free Phosphines by Stereoselective Hydrophosphination through DFT Method

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