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Theoretical Analysis of the Mechanism of the 1,3-Dipolar Cycloaddition of Benzodiazepine with N-Aryl-C-ethoxycarbonylnitrilimine

Journal of Chemistry. 2020;2020 DOI 10.1155/2020/8695405

 

Journal Homepage

Journal Title: Journal of Chemistry

ISSN: 2090-9063 (Print); 2090-9071 (Online)

Publisher: Hindawi Limited

LCC Subject Category: Science: Chemistry

Country of publisher: United Kingdom

Language of fulltext: English

Full-text formats available: PDF, HTML, ePUB, XML

 

AUTHORS


Khadija Nabih (Laboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP. 2390, Av. My Abdellah, Marrakech 40000, Morocco)

Mohamed Maatallah (Laboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP. 2390, Av. My Abdellah, Marrakech 40000, Morocco)

Abdesselam Baouid (Laboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP. 2390, Av. My Abdellah, Marrakech 40000, Morocco)

Abdellah Jarid (Laboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP. 2390, Av. My Abdellah, Marrakech 40000, Morocco)

EDITORIAL INFORMATION

Blind peer review

Editorial Board

Instructions for authors

Time From Submission to Publication: 16 weeks

 

Abstract | Full Text

In this work, the mechanism and regio- and no-periselectivity of the 1,3-dipolar cycloaddition reaction of 2,4-dimethyl-3H-1,5-benzodiazepine with N-aryl-C-ethoxycarbonylnitrilimine have been studied using the DFT method at the B3LYP/6-31G(d) level of theory. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. The two C=N sites of 2,4-dimethyl-3H-1,5-benzodiazepine are easily reached by the dipole, and the energy barrier between the reagents and the transition states is too weak. The secondary barriers are traversed by the heat released in the reaction medium after the crossing of the first TS, which facilitates the addition reaction and does not require high energy. The obtained results of this study are in good agreement with experimental outcomes.