A DFT study of the role of the Lewis acid catalysts in the [3+2] cycloaddition reaction of the electrophilic nitrone isomer of methyl glyoxylate oxime with nucleophilic cyclopentene

Nacereddine Abdelmalek Khorief; Layeb Hatem; Chafaa Fouad; Yahia Wassila; Djerourou Abdelhafid; Ramon Domingo Luis

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A DFT study of the role of the Lewis acid catalysts in the [3+2] cycloaddition reaction of the electrophilic nitrone isomer of methyl glyoxylate oxime with nucleophilic cyclopentene

机译：一种DFT研究路易斯酸催化剂在甲基乙醛酸甲基氧化甲醚甲基甲基氧化甲基甲基肟与亲核环戊烯的循环反应中的作用

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The molecular mechanism and stereoselectivity of the BF3 Lewis acid catalyzed [3 + 2] cycloaddition (32CA) reaction between C-methoxycarbonyl nitrone and cyclopentene has been theoretically studied using DFT methods at the MPWB1K/6-31G(d) computational level. The BF3 catalyst accelerates the 32CA reaction by decreasing the activation energy leading to the formation of the trans cycloadduct as the kinetic product, in agreement with the experimental data. Inclusion of solvent effects slightly increases the activation energy and decreases the exothermic character of the 32CA reaction as a consequence of a better solvation of nitrone than the transition state and the cycloadduct. The use of the lithium cation as LA catalyst does not make any remarkable change with respect to the BF3 catalyzed process. The nature of the mechanism has been also studied using the reactivity indices defined within the conceptual DFT.

机译：在理论上在MPWB1K / 6-31G（D）计算水平下理论上研究了C-甲氧基羰基亚甲酮和环戊烯与环戊烯之间的BF3路易斯酸催化[3 + 2]环加入（32Ca）反应的分子机制和立体选择性。通过降低导致跨环形加动器作为动力学产品的形成，BF3催化剂通过降低导致的激活能量，同时加速32CA反应，同时与实验数据一致。将溶剂效果的包含略微增加激活能量，并降低32CA反应的放热特征，因为亚硝酮的溶解比过渡状态和环绕体更好。使用锂阳离子作为La催化剂并不能相对于BF 3催化方法进行任何显着变化。还使用概念DFT中定义的反应性指数研究了该机制的性质。

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《RSC Advances》 |2015年第79期|共8页
作者
Nacereddine Abdelmalek Khorief; Layeb Hatem; Chafaa Fouad; Yahia Wassila; Djerourou Abdelhafid; Ramon Domingo Luis;
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作者单位

Univ Badji Mokhtar Annaba Fac Sci Dept Chim Lab Synth &

Biocatalyse Organ Annaba 23000 Algeria;

Univ Badji Mokhtar Annaba Fac Sci Dept Chim Lab Synth &

Biocatalyse Organ Annaba 23000 Algeria;

Univ Badji Mokhtar Annaba Fac Sci Dept Chim Lab Synth &

Biocatalyse Organ Annaba 23000 Algeria;

Univ Badji Mokhtar Annaba Fac Sci Dept Chim Lab Synth &

Biocatalyse Organ Annaba 23000 Algeria;

Univ Badji Mokhtar Annaba Fac Sci Dept Chim Lab Synth &

Biocatalyse Organ Annaba 23000 Algeria;

Univ Valencia Dept Quim Organ Unidad Invest Quim Organ Teor E-46100 Valencia Spain;

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1. A DFT study of the role of the Lewis acid catalysts in the [3+2] cycloaddition reaction of the electrophilic nitrone isomer of methyl glyoxylate oxime with nucleophilic cyclopentene [J] . Nacereddine Abdelmalek Khorief, Layeb Hatem, Chafaa Fouad, RSC Advances . 2015,第79期

机译：一种DFT研究路易斯酸催化剂在甲基乙醛酸甲基氧化甲醚甲基甲基氧化甲基甲基肟与亲核环戊烯的循环反应中的作用
2. Unravelling the mechanism and the origin of the selectivity of the [3+2] cycloaddition reaction between electrophilic nitrone and nucleophilic alkene [J] . Chafaa Fouad, Nacereddine Abdelmalek Khorief, Djerourou Abdelhafid Theoretical chemistry accounts . 2019,第12期

机译：解开电泳亚硝酮和亲核烯烃之间[3 + 2]环加入反应的机制和起源的起源
3. DFT Study on the Mechanisms and Diastereoselectivities of Lewis Acid-Promoted Ketene?Alkene [2 + 2] Cycloadditions: What is the Role of Lewis Acid in the Ketene and C = X (X = O, CH_2, and NH) [2 + 2] Cycloaddition Reactions? [J] . Yang Wang, Donghui Wei, Zhenyu Li, The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory . 2014,第24期

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机译：通过路易斯酸催化剂 - 亚硝酮和ACI-NITRO复合环加成的辅助，立体声和注射率控制1,3-偶极环加成反应 -

A DFT study of the role of the Lewis acid catalysts in the [3+2] cycloaddition reaction of the electrophilic nitrone isomer of methyl glyoxylate oxime with nucleophilic cyclopentene

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