A DFT Study of Mechanism, Diastereoselectivity, and Solvent Effects on the 1,3-Dipolar Cycloaddition Reaction between N-Methyltrichloromethylnitrone and Maleimide Derivatives

被引：0
作者：
Tliba, S. [1 ]
Yahia, W. [1 ,2 ]
Adjeroud, Y. [1 ,3 ]
Seddiki, K. [1 ,4 ]
Liacha, M. [1 ]
机构：
[1] BADJI Mokhtar Annaba Univ, Lab Synth & Organ Biocatalysis LSOB, Organ Synth & Med Chem Grp, POB12, Annaba 23000, Algeria
[2] Univ 20 August 1955, Fac Sci, Dept Chem, Skikda 21000, Algeria
[3] Univ Amar TELIDJI Laghouat, Fac Technol, Dept Common Core Sci & Technol, Laghouat 03000, Algeria
[4] Natl Higher Sch Technol & Engn, 2000 Educ Pl, Sidi Amar 23000, Annaba, Algeria
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2024年 / 94卷 / 06期
关键词：
1,3-dipolar cycloaddition; maleimide; isoxazolidines; DFT; nitrones; MICROWAVE-ASSISTED SYNTHESIS; ISOXAZOLIDINE DERIVATIVES; ORGANIC-REACTIONS; ON-WATER; INHIBITORS; NITRONES; ANTIBACTERIAL; EXPLORATION; DESIGN;
D O I：
10.1134/S107036322406015X
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Diastereoselectivity of the 1,3-dipolar cycloaddition of nitrone with some N-substituted maleimides was studied theoretically in gas phase and in solvents, using DFT methods at the B3LYP/6-31G(d) theoretical level. The reactivity indices indicate that nitrone is a moderate nucleophile whereas the maleimides are moderate electrophiles. Analysis of different energy profiles shows that these competitive reactions favour the formation of the exo cycloadducts, in all reactions. Solvent effect showed that water was the best solvent for this reaction, which is in agreement with the experiment.
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页码：1375 / 1384
页数：10
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