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Regio- and stereoselectivity of the [3+2] cycloaddition of nitrones with methyl-acetophenone: A DFT investigation.

Authors
  • Zouaghi, Mohamed Oussama1
  • Doggui, Mohamed Yassine1
  • Arfaoui, Youssef2
  • 1 Department of Chemistry, Laboratory of Characterizations, Applications and Modeling of Materials LR18ES08, University of Tunis El Manar, Tunisia. , (Tunisia)
  • 2 Department of Chemistry, Laboratory of Characterizations, Applications and Modeling of Materials LR18ES08, University of Tunis El Manar, Tunisia. Electronic address: [email protected]. , (Tunisia)
Type
Published Article
Journal
Journal of molecular graphics & modelling
Publication Date
Sep 01, 2021
Volume
107
Pages
107960–107960
Identifiers
DOI: 10.1016/j.jmgm.2021.107960
PMID: 34126545
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

A theoretical study of the regio- and stereoselectivities of the [3 + 2] cycloaddition reactions of nitrones with substituted alkene (methyl acetophenone) is investigated using density functional theory (DFT) and carried out at B3LYP/6-311+G(d,p) level. The reactivity of these cycloadditions is rationalized by FMO model, activation energy calculations, and philicity indexes. The electronic populations have been calculated from natural orbital, which based on charges by using NBO analysis, MK and CHelpG electrostatic population. The four possible pathways, fused and bridged regioisomeric modes, and the two stereoisomeric approaches endo and exo for the cycloaddition reactions are analyzed and discussed. Analysis of TS geometries and bond lengths demonstrate that these reactions follow a one-step mechanism with asynchronous transition states. The activation energy indicated a favored endo approach along the four reaction pathways. Copyright © 2021 Elsevier Inc. All rights reserved.

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