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

Abstract

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.