PMID: 15382865Sep 24, 2004Paper

Evidence for pi-pi electron donor-acceptor interactions between pi-donor aromatic compounds and pi-acceptor sites in soil organic matter through pH effects on sorption

Environmental Science & Technology
Dongqiang ZhuLinda S Lee

Abstract

Elucidation of molecular-level interactions controlling the sorption of organic compounds in soils is of major theoretical and practical interest. Sorption of pi-electron donor compounds, pentamethylbenzene (PMB), naphthalene (NAPH), and phenanthrene (PHEN), in a number of soils was found to increase with decreasing pH in the range of approximately pH 2.5-7. This behavior could not be attributed to pH-dependent alteration of the hydrophobic character of humic substances, pi-H-bonding, interaction with mineral surfaces, interaction with black carbons, solute coplanarity, or pH effects on solute activity coefficient. No significant effect of pH was observed for non-pi-donor hydrophobic compounds, whether planar or not: trans-1,2-dichlorocyclohexane (DCCH), hexachloro-1,3-butadiene (HCBD), 1,2,4-trichlorobenzene (TCB), 2,2',5,5'-tetrachlorobiphenyl, and 3,3',4,4'-tetrachlorobiphenyl. The opposite pH effect was observed for 2-nonanol and 2-nonanone, which are non-pi-donors, but capable of H-bonding. Also, no pH-dependent sorption was observed between the pi-donor PHEN and alumina, a model inorganic surface. We propose that the pi-donor solutes interact with pi-acceptor sites in soil organic matter (SOM), including aromatic rings wi...Continue Reading

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Citations

Oct 17, 2008·Environmental Science and Pollution Research International·Bo PanBaoshan Xing
Dec 23, 2011·Environmental Toxicology and Chemistry·Lunliang ZhangWei Chen
Mar 14, 2018·Environmental Science and Pollution Research International·Shixiang DaiWenjie Ren
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Dec 30, 2016·Environmental Science and Pollution Research International·Lu HanMengfang Chen
Mar 29, 2018·Environmental Science and Pollution Research International·Huilan ShiWenhao Pang
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Jan 5, 2011·Environmental Science & Technology·Guido Bronner, Kai-Uwe Goss

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