Understanding the Regioselectivity and the Molecular Mechanism of [3+2] Cycloaddition Reactions between Nitrous Oxide and Conjugated Nitroalkenes: A DFT Computational Study

被引：12

作者：

Dresler, Ewa ^{[1
]}

Wroblewska, Aneta ^{[2
]}

Jasinski, Radomir ^{[3
]}

机构：

[1] Inst Synth Macromolecularorgan Compounds, Lukasiewicz Res Network, Energetykow 9, PL-47225 Kedzierzyn Kozle, Poland

[2] Polish Acad Sci, Ctr Mol & Macromol Studies, Sienkiewicza 112, PL-90363 Lodz, Poland

[3] Cracow Univ Technol, Inst Organ Chem & Technol, Warszawska 24, PL-31155 Krakow, Poland

来源：

MOLECULES | 2022年 / 27卷 / 23期

关键词：

3+2] cycloaddition; nitrous oxide; nitroalkenes; molecular mechanism; molecular electron density theory; conceptual density functional theory; QUANTITATIVE CHARACTERIZATION; 1,3-DIPOLAR CYCLOADDITION;

D O I：

10.3390/molecules27238441

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Regiochemical aspects and the molecular mechanism of the [3 + 2] cycloaddition between nitrous oxide and conjugated nitroalkenes were evaluated on the basis of the wb97xd/6-311 + G(d) (PCM) computational study. It was found that, independently of the nature of the nitroalkene, all considered processes are realized via polar, single-step mechanisms. All attempts at the localization of hypothetical zwitterionic intermediates were unsuccessful. Additionally, the DFT computational study suggested that, in the course of the reaction, the formation of respective Delta(2)-4-nitro-4-R-1-5-R-2-1-oxa-2,3-diazolines was preferred from the kinetic point of view.

引用

页数：9

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