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1,3-dipolar cycload...
1,3-dipolar cycloaddition between substituted phenyl azide and 2,3-dihydrofuran
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- Bekhradnia, Ahmadreza R. (author)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology
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Arshadi, Sattan (author)
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Siadati, S. A. (author)
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(creator_code:org_t)
- Springer Science and Business Media LLC, 2014
- 2014
- English.
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In: Chemical Papers. - : Springer Science and Business Media LLC. - 0366-6352 .- 1336-9075. ; 68:2, s. 283-290
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Abstract
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- 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
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- DFT method
- substituted phenyl azide
- 2
- 3-dihydrofuran
- 1
- 3-dipolar cycloadditions
- Hammett
- DIPOLAR APROTIC-SOLVENTS
- DIELS-ALDER REACTION
- FUKUI FUNCTIONS
- INSIGHTS
- MECHANISM
- DENSITY
Publication and Content Type
- ref (subject category)
- art (subject category)
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