Mechanistic DFT Study of 1,3-Dipolar Cycloadditions of Azides with Guanidine.

ABSTRACT: Density functional calculations SMD(chloroform)//B3LYP/6-311+G(2d,p) were employed in the computational study of 1,3-dipolar cycloadditions of azides with guanidine. The formation of two regioisomeric tetrazoles and their rearrangement to cyclic aziridines and open-chain guanidine products were modeled. The results suggest the feasibility of an uncatalyzed reaction under very drastic conditions since the thermodynamically preferred reaction path (a), which involves cycloaddition by binding the carbon atom from guanidine to the terminal azide nitrogen atom, and the guanidine imino nitrogen with the inner N atom from the azide, has an energy barrier higher than 50 kcal mol^-1. The formation of the other regioisomeric tetrazole (imino nitrogen interacts with terminal N atom of azide

SUBMITTER: Antol I 

PROVIDER: S-EPMC10004754 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature