关键词: N-亚硝基哌嗪, 邻基参与作用, 双区理论, 从头算, 密度泛函理论

Abstract: The anchimeric assistant mechanism of the second electrophilic region on β-methylnitrosopiperazine was studied by using ab initio and density functional theory(DFT) method with the 6-311G(d) basis set. The results show that the anchimeric assistance of N' atom on the piperazine ring or the oxygen atom on the N'-substituted group enhances the reactivity of β-methylnitrosopiperazine metabolites, which can be used to explain the phenomenon that the carcinogenicity of methyl substituted N-nitrosopiperazines is much more potent than that of their parent compounds. This research provids a theoretical evidence for the formation of the second electrophilic region on the γ-positions of N-nitrosopiperazines in their carcinogenic metabolism.

Key words: N-Nitrosopiperazine, Anchimeric assistance, Di-region theory, Ab initio, DFT