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1,3-dipolar cycloaddition between substituted phenyl azide and 2,3-dihydrofuran

Författare och institution:
A. R. Bekhradnia (Institutionen för kemi och molekylärbiologi); Sattan Arshadi (-); S. A. Siadati (-)
Publicerad i:
Chemical Papers, 68 ( 2 ) s. 283-290
Artikel, refereegranskad vetenskaplig
Sammanfattning (abstract):
A theoretical study was performed on the 1,3-dipolar cycloaddition between 2,3-dihydrofuran and substituted phenyl azide using Density Functional Theory (DFT) in combination with a 6-311++G(d,p) basis set. The optimum geometries for reactant, transition state and product, as well as the kinetic data, rate constants and reaction constant (rho) were investigated to rationalise the substitution effects and reaction rates of the 1,3-dipolar cycloaddition process in various solvents. The DFT calculation and Frontier Molecular Orbital (FMO) theory as well as the atomic Fukui indices show that the electron-withdrawing substituents enhance the reaction constant (rho > 0), especially in polar aprotic solvents. Consequently, small changes in the rate constant of the reaction in various solvents and geometric similarity between reactants and transition state structures were suggested as the early transition state mechanism for electron-withdrawing substituents. In addition, the slope of the Hammett plot and susceptibility of the reaction to electron-withdrawing substituents in various solvents confirmed the mechanism. (C) 2013 Institute of Chemistry, Slovak Academy of Sciences
Ämne (baseras på Högskoleverkets indelning av forskningsämnen):
DFT method, substituted phenyl azide, 2,3-dihydrofuran, 1,3-dipolar cycloadditions, Hammett, DIPOLAR APROTIC-SOLVENTS, DIELS-ALDER REACTION, FUKUI FUNCTIONS, INSIGHTS, MECHANISM, DENSITY
Postens nummer:
Posten skapad:
2013-12-02 15:53
Posten ändrad:
2013-12-03 10:40

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