E-2-(Trimethylsilyl)-1-Nitroethene 与 Arylonitrile N-Oxides (3+2) Cycloaddition 反应的区域选择性和分子机理之谜：分子电子密度理论（MEDT）量子化学研究。

IF 4.2 2区化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Molecules Pub Date : 2025-02-19 DOI:10.3390/molecules30040974

Mikołaj Sadowski, Ewa Dresler, Radomir Jasiński

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The Puzzle of the Regioselectivity and Molecular Mechanism of the (3+2) Cycloaddition Reaction Between E-2-(Trimethylsilyl)-1-Nitroethene and Arylonitrile N-Oxides: Molecular Electron Density Theory (MEDT) Quantumchemical Study.

The regioselectivity and molecular mechanism of the (3+2) cycloaddition reaction between E-2-(trimethylsilyl)-1-nitroethene and arylonitrile N-oxides were explored on the basis of the ωB97XD/6-311+G(d) (PCM) quantumchemical calculations. It was found that the earlier postulate regarding the regioselectivity of the cycloaddition stage should be undermined. Within our research, several aspects of the title reaction were also examined: interactions between reagents, electronic structures of alkenes and nitrile oxides, the nature of transition states, the influence of the polarity solvent on the reaction selectivity and mechanism, substituent effects, etc. The obtained results offer a general conclusion for all of the important aspects of some groups of cycloaddition processes.

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来源期刊

Molecules 化学-有机化学

CiteScore

7.40

自引率

8.70%

发文量

7524

审稿时长

1.4 months

期刊介绍： Molecules (ISSN 1420-3049, CODEN: MOLEFW) is an open access journal of synthetic organic chemistry and natural product chemistry. All articles are peer-reviewed and published continously upon acceptance. Molecules is published by MDPI, Basel, Switzerland. Our aim is to encourage chemists to publish as much as possible their experimental detail, particularly synthetic procedures and characterization information. There is no restriction on the length of the experimental section. In addition, availability of compound samples is published and considered as important information. Authors are encouraged to register or deposit their chemical samples through the non-profit international organization Molecular Diversity Preservation International (MDPI). Molecules has been launched in 1996 to preserve and exploit molecular diversity of both, chemical information and chemical substances.