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

Subject Areas :

Marzieh Omrani ¹ , Tayebeh Hosseinnejad ²

1 - Department of Chemistry, Alzahra University, Vanak, Tehran, Iran
2 - Department of Chemistry, Alzahra University, Vanak, Tehran, Iran

Received: 2022-01-26 Accepted : 2022-01-26 Published : 2020-12-01

Keywords: 1, 2, 3-triazole, density functional theory, 1, 3-Dipolar cycloaddition, polarized continuum model,

Abstract :

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-membered heterocycles. 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, we investigated the structure and energy of transition states in the reaction path and assessed the trends in the calculated activation barriers for the1,3-dipolar cycloaddition of azides with various substituted cyclooctynes in the gas and solution phases to interpret theoretically the origin of regioselectivity in the synthesis of disubstituted 1,2,3-triazole derivatives.