• 作者：Dimitar Mehandjiev ^A1 ; Mihail Atanasov ^A1 ; Anton Naydenov ^A1
• 关键词：Indeno[1 路 2 路 3- c 路 d ]pyrene ; Ozonation ; MNDO-method
• 刊名：Monatshefte für Chemie / Chemical Monthly
• 出版时间：October 1998
• 出版年：1998
• 期刊代码：99_0026-9247
• 类别：ch
• 卷：129
• 期：10
• 页码：999-1005
• 数据来源：sp

Summary. Calculations on the strongly cancerogenic indeno[1,2,3-c,d]pyrene and all its possible primary and secondary ozonides by the MNDO method indicate the breaking of the C₂₁-C₂₂ bond of the pyrene fragment as the energetically most favourable first step of the oxidative degradation. Localization energies calculated within the simple Hückel model predict that the attack of the C₂₁-C₂₂ pair by ozone is most probably also kinetically the most preferred reaction path. The rather low localization energy of C₂₀ in the pyrene fragment indicates the possibility of competitive reactions between ozonolysis and the formation of phenols and quinones. The theoretical results are supported by experimental findings on the ozonation of indeno[1,2,3-c,d]pyrene in aqueous medium.