Iranian Journal of Chemistry

Iranian Journal of Chemistry

A theoretical study on the regio- and chemoselectivity of the cycloaddition reaction of nitrone with vinylidene cyclopropane through density functional theory (DFT) method

Document Type : Original Article

Authors
mina Haghdadi 1
Mahshid Hamzehloueian 2
1 Department of chemistry-Babol branch. islamic azad university of Babol.Iran
2 Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran
10.22036/cr.2024.375449.1196
Abstract
The molecular mechanism of the regio- and chemoselectivity of the cycloaddition reaction of nitrone 1 and vinylidene cyclopropane 2 has been investigated using density functional theory method at M06-2X/cc-pVDZ level of theory. All the possible reaction pathways were investigated and the factors affecting the selectivity were systematically studied. The analysis of the calculation results showed that the most favorable reaction paths in terms of kinetics and thermodynamics are the Regio 1 and Regio 4 pathways. It is also expected that the major product resulting from the cycloaddition reaction is a mixture of two isomers 3 and 6. The analysis of the global reactivity indices of the reactants indicates that vinylidene cyclopropane is a nucleophile and nitrone act as an electrophile in this reaction. The results of the electron localization function analysis of some selected points along the intrinsic reaction coordinate shows the most preferred pathway where the reaction proceeds via two-stage one-step mechanism.

Graphical Abstract

A theoretical study on the regio- and chemoselectivity of the cycloaddition reaction of nitrone with vinylidene cyclopropane through density functional theory (DFT) method
Keywords
regioselectivity
chemoselectivity
nitrone
vinylidene cyclopropane
density functional theory

Subjects

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  • Receive Date 09 December 2022
  • Revise Date 27 October 2023
  • Accept Date 11 January 2024