Copper Catalyzed Cycloaddition Reaction of Azidomethyl Benzene With 2,2-Di(prop-2-yn-1-yl)propane-1,3-diol: DFT and QTAIM Investigation

In this study, the cycloaddition of azidomethyl benzene with 2,2-di(prop-2-yn-1-yl)propane-1,3-diol in the presence of copper catalyst was modeled electronically and thermodynamically in the gas and two solution phases, using quantum chemistry methods. In this line, we investigated some aspects of products and their related transition states through two plausible catalytic reaction pathways, leading to the unexpected synthesis of a statistical mixture of mono and bistriazoles, from structural and energetic viewpoints. The obtained results revealed that production of mono and bistriazole mixture can be essentially attributed to the balance of thermochemical and kinetical factors. Additionally, we analyzed topologically the electron density through quantum theory of atoms in molecules. In this line, electron density, its laplacian and electronic energy density properties were assessed on key bond and ring critical points to explicate more clearly the origins of electronic stability in triazole and bis-triazole products and their associated transition states