Insights into the Formation and Isomerization of the Benzene Metabolite Muconaldehyde and Related Molecules: Comparison of Computational and Experimental Studies of Simple, Benzo-Annelated, and Bridge

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• 作者：Jessica Morgan ; Arthur Greenberg
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：July 16, 2010
• 年：2010
• 卷：75
• 期：14
• 页码：4761-4768
• 全文大小：841K
• 年卷期：v.75,no.14(July 16, 2010)
• ISSN：1520-6904

文摘

2,8-Dioxabicyclo[5.1.0]octa-3,5-diene (“2,3-epoxyoxepin”) has been postulated as an intermediate in ring-opening metabolism of benzene. Density functional theory (B3LYP/6-31G*) is employed to study the activation and reaction energies for ring-opening isomerization of 2,3-epoxyoxepin, its 4,5-benzo derivative, and its 3,6-hexamethylene derivative. The results are compared with published experimental data. The markedly different fates of these three molecules suggest a means for testing the postulated metabolic pathway.