Quantum chemistry study on the regioselective behavior of 1,3-dipolar cycloaddition reaction of azides with various substituted cyclooctynes

The 1,3-Dipolar cycloaddition reactions are the classic reaction in modern synthetic organic chemistry.The Huisgen cycloaddition is the reaction of a dipolarophile with a 1,3-dipolar compound that leads to 5-memberedheterocycles. With the goal of identifying alkyne-like reagents for use in azide-alkyne Huisgen cycloaddition reactions,we used density functional theory (DFT) and polarized continuum model (PCM) computations. In this respect, weinvestigated the structure and energy of transition states in the reaction path and assessed the trends in the calculatedactivation barriers for the1,3-dipolar cycloaddition of azides with various substituted cyclooctynes in the gas andsolution phases to interpret theoretically the origin of regioselectivity in the synthesis of disubstituted 1,2,3-triazolederivatives.

کلیدواژه ها:

1 ، 3-Dipolar cycloaddition ، 1 ، 2 ، 3-triazole ، regioselectivity ، density functional theory ، polarized continuum model