10.48317/IMIST.PRSM/MORJCHEM-V6I1.7935
M. El Idrissi, M. Moumou,, A. El Haib, R. El Ajlaoui,
A. Benharref, A. El Hajbi, S. Abouricha, A. Zeroual,
The mechanism, the chemoselectivity and the regioselectivity of the 1-Benzyl-4-ethynyl-1H-[1,2,3]triazole and 1-Azidomethyl-4-tert-butyl-benzene in [3+2] cycloaddition reactions: a DFT study
Moroccan Journal of Chemistry
2017
[3+2] cycloaddition, chemoselectivity, regioselectivity, PES, Parr functions.
2017-02-19
2017-02-19
2017-09-25
2020-09-09
en
Article
24-685-7935
Mor. J. Chem. 6N°1 (2018) 14-21 Pages
The [3 + 2] cycloaddition (32CA) reaction between the 1-Benzyl-4-ethynyl-1H-[1,2,3]triazole and 1-Azidomethyl-4-tert-butyl-benzen has been studied within the Density Functional Theory (DFT) B3LYP/6-311G(d,p) computational level. Analysis of the conceptual DFT reactivity indices allows the explanation of the reactivity, and the chemo- and regioselectivity experimentally observed. The possible chemoselective channels and ortho/meta regioselective channels were explored and characterized. Analysis of the energies associated with the different reaction pathways indicates that the 32CA reactions of the between the 1-benzyl-4-ethynyl-1H-[1,2,3]triazole and 1-azidomethyl-4-tert-butyl-benzene is highly chemioselective and meta regioselectivitie, in agreement with the experimental outcomes.
Moroccan Journal of Chemistry, Vol 6, No 1 (2018)