Computational study of solvent effect on ruthenium catalyzed click synthesis of 1,2,3-triazoles.
کد مقاله : 1028-PHYSCHEM20
سهیلا مهدویان *، 1طیبه حسین نژاد، 2مجید ممهد هروی
1دانشگاه الزهرا
2دانشکده شیمی فیزیک-دانشگاه الزهرا
چکیده مقاله:
In this study, ruthenium catalyzedazide-alkyne cycloaddition reaction mechanism has been modeled by quantum mechanical methods. In this respect, we have investigated regioselectivity in azide-alkyne reaction on the presence of ruthenium catalysts in solution phases. Density functional theory and polarized continuum model were utilized to demonstrate that 1,5-disubstituted triazole is the main product. We demonstrated that the presence of Cp*RuCl(PH3)2 catalyst has an important role on the energy barriers of transition states and so the regioselective behavior of synthesis. The thermodynamic stability of Ru-azide-alkyne complexes in transition state structures was comparatively evaluated in the presence of solvent. It was shown that the production of 1,5-disubstituted triazoles in 1,2-dichloroethane solution is more favorable thermodynamically than dimethylformamide.
کلیدواژه ها:
Ruthenium catalyst; Disubstituted 1,2,3-triazoles; Click reaction; DFT computations; Polarized continuum model.
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