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  3. Volume 17, Number 3, 2023
  4. [3+2] Cycloaddition of N-tert-Butyl, -(4-Trifluoromethyl)-Phenylnitrone with Methacrolein: Theoretical Investigation

[3+2] Cycloaddition of N-tert-Butyl, -(4-Trifluoromethyl)-Phenylnitrone with Methacrolein: Theoretical Investigation

JCCT.
2023;
Volume 17, Number 3
: pp. 518 - 531
https://doi.org/10.23939/chcht17.03.518
Authors:
  1. Khaoula Kouchkar
  2. Youcef Boumedjane
  3. Salah Eddine Hachani
1
Group of Computational and Pharmaceutical Chemistry, LMCE Laboratory, University of Biskra
2
Group of Computational and Pharmaceutical Chemistry, LMCE Laboratory, University of Biskra
3
Applied Chemistry Laboratory, University of Biskra

In this scientific contribution, regio- and diastereo- selectivity of [3+2] cycloaddition (32CA) of N-tert-butyl,α-(4-trifluoromethyl)-phenylnitrone (1) with methacrolein (2) were investigated using DFT method at B3LYP/6-31(d) computational level in gas and dichloromethane solvent. The molecular electrostatic potential MESP was used to show the most active centers in the examined molecules. Global and local reactivity indices as well as thermodynamic parameters have been calculated to explain the regioselectivity and stereoselectivity for the selected reaction. The possible chemoselective ortho/meta regioselectivity and stereo- (endo/exo) isomeric channels were investigated. Our theoretical results give important elucidations for the possible pathways related to the studied 32CA reaction.

[3+2] cycloaddition
N-tert-butyl
α-(4- trifluoromethyl)-phenyl
methacrolein
DFT
regioselectivity
stereoselectivity
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