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. (1399). Investigation on the effect of trifluoromethyl group on the [3+2] cycloadditions of thiocarbonyl S-methanides with α, β-unsaturated ketones: A theoretical study using DFT. , 17(Issue 1 (Spring and Summer 2020) 1 and 2), 29-38.
. "Investigation on the effect of trifluoromethyl group on the [3+2] cycloadditions of thiocarbonyl S-methanides with α, β-unsaturated ketones: A theoretical study using DFT". , 17, Issue 1 (Spring and Summer 2020) 1 and 2, 1399, 29-38.
. (1399). 'Investigation on the effect of trifluoromethyl group on the [3+2] cycloadditions of thiocarbonyl S-methanides with α, β-unsaturated ketones: A theoretical study using DFT', , 17(Issue 1 (Spring and Summer 2020) 1 and 2), pp. 29-38.
. Investigation on the effect of trifluoromethyl group on the [3+2] cycloadditions of thiocarbonyl S-methanides with α, β-unsaturated ketones: A theoretical study using DFT. , 1399; 17(Issue 1 (Spring and Summer 2020) 1 and 2): 29-38.

Investigation on the effect of trifluoromethyl group on the [3+2] cycloadditions of thiocarbonyl S-methanides with α, β-unsaturated ketones: A theoretical study using DFT

Journal of Physical & Theoretical Chemistry
دوره 17، Issue 1 (Spring and Summer 2020) 1 and 2، آبان 2020، صفحه 29-38  XML اصل مقاله (498.87 K)
نوع مقاله: Research Paper
چکیده
A [3+2] cycloaddition (32CA) reaction among a thiocarbonyl ylide (TCY 2) with (E)-4,4,4-trifluoro-4-phenylbut-3-en-2-one (TFB 4) as an electron-deficient enone in tetrahydrofuran (THF) were studied within the Molecular Electron Density Theory (MEDT), at the DFT-B3LYP/6-31G(d) computational level to analysis energetics, selectivities, and mechanistic aspects. The reaction can progress in four competitive 32CA reaction paths. An analysis of the density functional theory (DFT)-based reactivity indices shows that TCY 2 is a strong nucleophile and TFB 4 is a strong electrophile. Parr function analysis at the reactive sites of reagents demonstrates that the C1-C6 attack should be the more favorable regioselective channel in 32CA reaction of TCY 2 toward TFB 4. An exploration of computed relative Gibbs free energies implies that the studied 32CA reaction leads to thiolanes 4 as the unique cycloadduct, in complete agreement with the experimental outcomes. The global electron density transfer (GEDT) value at the energetically most preferred transition state TS 1 reveals that this pseudoradical type (pdr-type) 32CA reactions exhibits a notable polar character.
کلیدواژه‌ها
Fluorinated enones؛ Thiocarbonyl ylides؛ Chemoselectivity؛ Regioselectivity؛ DFT study
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تعداد مشاهده مقاله: 123
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