Regio- and stereoselectivities of the [3 + 2] cycloaddition reactions of dibromoformaldoxime and (Z)-, (E)-3-(4-chlorobenzylidene)-1-methylindolin-2-one have been investigated using density functional theory. The results show that the experimental observations are predicted correctly by the PBE0-D3BJ/Def2TZVPP level of theory, unlike the frequently employed functional, i.e., B3LYP/6-31G(d). The distortion/interaction analyses revealed that these [3 + 2] cycloaddition reactions are under distortion control, and FMO calculations indicated a dominant HOMO_{multiple bond system} to LUMO_TAC interaction. From the molecular electron density theory perspective, these [3 + 2] cycloaddition reactions show non-polar character and the bromo nitrile oxide under study were classified as zwitterionic species from the topological analysis of the electron localization function (ELF).

使用密度泛函理论研究了二溴甲醛肟和(Z) -, (E) -3-(4-氯亚苄基)-1-甲基二氢吲哚-2-酮的[3 + 2]环加成反应的区域选择性和立体选择性。结果表明，与常用泛函（即 B3LYP/6-31G(d)）不同，PBE0-D3BJ/Def2TZVPP 理论水平能够正确预测实验观测结果。畸变/相互作用分析表明，这些 [3 + 2] 环加成反应处于畸变控制之下，FMO 计算表明LUMO _TAC的主要 HOMO_{多重键系统}相互作用。从分子电子密度理论的角度来看，这些[3+2]环加成反应表现出非极性特征，并且根据电子局域函数（ELF）的拓扑分析，所研究的溴代腈氧化物被归类为两性离子物种。