Revealing the mechanism, Regio- and stereo selectivity and solvent effects of [3+2] cycloaddition reactions involving N-benzyl fluoro nitrone and electron-deficient alkynes

被引：3

作者：

Boutiddar, Rachid ^{[1
,2
]}

Abbiche, Khalid ^{[1
,2
,3
]}

Izzaouihda, Safia ^{[1
,2
]}

Taleb, Abdelaziz Ait ^{[1
]}

El Baraka, Noureddine ^{[1
]}

Errai, Mohamed ^{[1
]}

Makarim, Hassna Abou El ^{[2
]}

El Hammadi, Abdellatif ^{[1
]}

Hochlaf, Majdi ^{[4
]}

机构：

[1] Ibn Zohr Univ, Polydisciplinary Fac Taroudant, Anal Modeling Engn Nat Subst & Environm Lab, BP 271, Taroudant 83000, Morocco

[2] Univ Mohammed 5, Fac Sci Rabat, Lab Spect Modelisat Mol Mat Nanomat Eau & Environm, LS3MN2E,CERNE2D, BP1014, Rabat, Morocco

[3] Ibn Zohr Univ, Fac Sci, Appl Chem Phys Lab, BP 8106 Cite Dakhla, Agadir, Morocco

[4] Univ Gustave Eiffel, COSYS, IMSE, 5 Bd Descartes, F-77454 Champs Sur Marne, France

来源：

COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2024年 / 1237卷

关键词：

N -benzyl fluoro nitrone; Alkynes; DFTs; cycloaddition reaction; MEDT; REACTIVITY; LOCALIZATION; ISOXAZOLINE; DERIVATIVES;

D O I：

10.1016/j.comptc.2024.114665

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The [3 + 2] cycloaddition reactions (32CA) between N-benzyl fluoro nitrone and electron-deficient dipolarophiles alkynes have been studied using molecular electron density theory at the B3LYP-D3/6-31G(d) level. The findings indicate that, in these 32CA reactions, a one-step mechanism is in play with asynchronous transition states. The topological analyses of these transition states are consistent with the presence of non-covalent interactions at the bonding regions between atoms. The analysis of the energy profile in gas phase and in the presence of solvents indicates a preference for a specific site addition over the others. Parr functions were thus used to justify such regioselectivity. In addition, we show that solvents do not modify the regioselectivity achieved, but it increases the activation energies and reduces the exothermic nature of this 32CA reaction. The present findings are in agreement with the experimental results.

引用

页数：13

共 63 条

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