Microscopic mechanism of light-induced tetrazole-quinone 1,3-dipolar cycloaddition: a MS-CASPT2 theoretical investigation.

ABSTRACT: Recently, experimentalists have developed a green and efficient method to synthesize pyrazole-fused quinones through light-induced tetrazole-quinone 1,3-dipole cycloadditions. However, the underlying microscopic mechanisms remain to be clarified. In this work, we have employed several electronic structure calculation methods (MS-CASPT2, CASSCF, DFT) to systematically explore the microscopic mechanism of related light-induced reactions and deactivation pathways. Upon excitation with ultraviolet light, one of the original reactants 2-(4-fluorophenyl)-5-phenyl-2H-tetrazole (FPT) reaches its S₁ excited state. After that, due to the ultrahigh energy and the small energy barrier, the FPT molecule breaks the N2-N3 and N4-C5 bonds sequentially, removing the nitrogen atom finally

SUBMITTER: He Y 

PROVIDER: S-EPMC9042216 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature