Mechanisms of nitrogen dioxide reactions: initiation of lipid peroxidation and the production of nitrous Acid.

作者: W. A. PRYOR , J. W. LIGHTSEY

DOI: 10.1126/SCIENCE.214.4519.435

关键词: Hydrogen atom abstractionNitrous acidLinolenateCyclohexeneAutoxidationAlkeneNitrogen dioxideChemistryMedicinal chemistryNitrogenOrganic chemistry

摘要: The reactions of nitrogen dioxide with cyclohexene have been studied as a model for the that occur between in smoggy air and unsaturated fatty acids pulmonary lipids. As predicted from earlier studies at high concentrations, this gas reacts predominantly by addition to double bond concentrations 1 percent (10,000 parts per million) 40 nitrogen; presence or oxygen, reaction initiates autoxidation alkene. However, below 100 million nitrogen, almost exclusively abstraction allylic hydrogen; unexpected also alkene oxygen air, but it leads production nitrous acid rather than product containing nitro group attached carbon atom. can react amines produce nitrosamines. Moreover, nitrite ion produced hydrogen mechanism would be expected diffuse throughout body, unlike nitrated lipids confined cavity. These findings confirmed methyl oleate, linoleate, linolenate; some kinetic features dioxide—initiated these studied.

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