PMID: 18200858Jan 19, 2008Paper

The partitioning of PAHs to egg phospholipids facilitated by copper and proton binding via cation-pi interactions

Environmental Science & Technology
Xiaolei QuDongqiang Zhu

Abstract

The partitioning to lipid-containing solids (cell membranes, natural organic matters) plays an important role in the fate of organic pollutants. We herein studied sorption of a series of aromatic compounds from aqueous solution to gel-phase egg phospholipids. The regression line describing the free-energy relationship between lipid-water distribution coefficient (Kd) and n-octanol-water partition coefficient (K(OW)) for the high-polar compounds (phenolics, dinitrobenzene, trinitrobenzene) is displaced upward relative to the low-polar compounds (chlorobenzenes, polycyclic aromatic hydrocarbons (PAHs), nitrobenzene, dichlorobenzonitrile), suggesting additive polar extra-interactions besides hydrophobic effects in sorption. Binding of Cu2+ or decreasing pH increases sorption of the three and four-ring PAHs but not the rest compounds. These results led us to propose a specific sorption mechanism, cation-pi bonding between PAHs and complexed metal ions or protonated amine groups of phospholipids. The Cu(2+)-PAH complexation in solution was supported by the observation that PAHs enhance the saturated solubility of CuSO4 in chloroform, and the enhancement correlates with pi-donor strength of PAH (pyrene > phenanthrene > naphthalene). ...Continue Reading

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Citations

Mar 6, 2009·Environmental Science and Pollution Research International·Dan-Hua Zhao, Hong-Wen Gao
Nov 14, 2012·Chemical Reviews·A Subha Mahadevi, G Narahari Sastry
Mar 9, 2012·Environmental Science & Technology·A Patricia TcaciucPhilip M Gschwend
Oct 13, 2017·Environmental Science and Pollution Research International·Xiaoyong LiaoXiulan Yan
Aug 14, 2013·Chemistry, an Asian Journal·Yubing SunXiangke Wang
Jan 21, 2015·Journal of Environmental Quality·Yuqiang TaoShanying Li
Jun 24, 2018·Environmental Geochemistry and Health·Injeong KimSang Don Kim
Mar 25, 2020·Environmental Science and Pollution Research International·Bingyu WangJing Wang
Oct 14, 2017·Environmental Science & Technology·Lili YangYang Xu
Jul 21, 2010·Bioresource Technology·Jiao-Rong RenHong-Wen Gao

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