2- 未取代咪唑 N-氧化物与缺电子烯烃的相互作用：量子化学分析

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-10-26 DOI:10.1007/s11172-024-4370-z

Yu. M. Selivantev, V. S. Mityanov, E. S. Uvarova, F. A. Kolokolov, A. N. Morozov, O. A. Raitman

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引用次数: 0

摘要

模型化合物 N-1,4,5-三甲基-1H-咪唑-3-氧化物与缺电子烯烃（包括 2-(4-甲氧基亚苄基)丙二腈、(E)-2-氰基-3-(4-甲氧基苯基)丙烯酸乙酯）之间的反应、密度泛函理论对 2-苯甲酰基-3-(4-甲氧基苯基)丙烯腈和 5-(4-甲氧基苯亚甲基)-2,2-二甲基-1,3-二恶烷-4,6-二酮进行了理论研究。结果表明，根据烯烃分子中抽电子取代基的类型，反应既可以通过 1,3-二极环加成机制进行，也可以通过迈克尔加成机制进行。对反应路径进行了计算，并确定了中间体结构。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Interaction of 2-unsubstituted imidazole N-oxides with electron-deficient olefins: a quantum chemical analysis

Reactions between the model compound N-1,4,5-trimethyl-1H-imidazole-3-oxide and electron-deficient olefins including 2-(4-methoxybenzylidene)malononitrile, (E)-ethyl-2-cyano-3-(4-methoxyphenyl)acrylate, 2-benzoyl-3-(4-methoxyphenyl)acrylonitrile, and 5-(4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione were theoretically studied in terms of the density functional theory. It was demonstrated that the reactions can proceed either by the 1,3-dipolar cycloaddition mechanism or by the Michael addition mechanism depending on the type of electron-withdrawing substituents in the olefin molecule. The reaction pathways were calculated and the intermediate structures were determined.

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.