Molecular simulation of polycyclic aromatic hydrocarbon sorption to black carbon

References

• Govers , HAJ , Krop , HB , Parsons , JR , Tambach , T and Kubicki , JD . 2002 . Dissolved organic carbon–contaminant interaction descriptors found by 3D force field calculations . SAR QSAR Environ. Res. , 13 : 271 – 280 .
   PubMed Web of Science ®Google Scholar
• Govers , HAJ , Van Roon , A and Parsons , JR . 2003 . Calculation of the interaction between dissolved organic carbon and organic micropollutants by three dimensional force field methods . Environ. Toxicol. Chem. , 22 : 753 – 759 .
   PubMed Web of Science ®Google Scholar
• Govers , HAJ , De Voogt , P , Kwast , O and Bleeker , EAJ . 2002 . Membrane–contaminant interaction found by 3D force field calculations . SAR QSAR Environ. Res. , 13 : 135 – 143 .
   PubMed Web of Science ®Google Scholar
• Van Roon , A , Parsons , JR and Govers , HAJ . 2005 . Cytochrome P450cam–monoterpene interactions. Prediction of product profiles for monoterpene hydroxylation using a calibrated 3D force field . SAR QSAR Environ. Res. , 16 : 369 – 384 .
   PubMed Web of Science ®Google Scholar
• Bucheli , TD and Gustafsson , Ö . 2000 . Quantification of the soot–water distribution coefficient of PAHs provides mechanistic basis for enhanced sorption observations . Environ. Sci. Technol. , 34 : 5144 – 5151 .
   Web of Science ®Google Scholar
• Cornelissen , G , Gustafsson , Ö , Bucheli , TD , Jonker , MTO , Koelmans , AA and Van Noort , PCM . 2005 . Extensive sorption of organic compounds to black carbon, coal, and kerogen in sediments and soils: Mechanisms and consequences for distribution, bioaccumulation, and biodegradation . Environ. Sci. Technol. , 39 : 6881 – 6895 .
   PubMed Web of Science ®Google Scholar
• Koelmans , AA , Jonker , MTO , Cornelissen , G , Bucheli , TD , Van Noort , PCM and Gustafsson , Ö . 2006 . Black carbon: the reverse of its dark side . Chemosphere , 63 : 365 – 377 .
   PubMed Web of Science ®Google Scholar
• Kubicki , JD and Apitz , SE . 1999 . Models of natural organic matter and interactions with organic contaminants . Org. Geochem. , 30 : 911 – 927 .
   Web of Science ®Google Scholar
• Schulten , H-R . 1999 . Interactions of dissolved organic matter with xenobiotic compounds: molecular modeling in water . Environ. Toxicol. Chem. , 18 : 1643 – 1655 .
   Web of Science ®Google Scholar
• Diallo , MS , Faulon , J-L , Goddard , WA III and Johnson , JH Jr . 2001 . “ Binding of hydrophobic organic compounds to dissolved humic substances: a predictive approach based on computer assisted structure elucidation, atomistic simulations and Flory–Huggins solution theory ” . In Humic Substances: Structures, Models and Functions , Edited by: Ghabbour , EA and Davies , G . 221 – 237 . Cambridge : The Royal Society of Chemistry .
   Google Scholar
• Schulten , H-R , Thomsen , M and Carlsen , L . 2001 . Humic complexes of diethyl phthalate: molecular modelling of the sorption process . Chemosphere , 45 : 357 – 369 .
   PubMed Web of Science ®Google Scholar
• Kubicki , JD and Trout , CC . 2003 . “ Molecular modeling of fulvic and humic acids: charging effects and interactions with Al3+, benzene, and pyridine ” . In Geochemical and hydrological reactivity of heavy metals in soils , Edited by: Kingery , WL and Selim , HM . 113 – 143 . Boca Raton, FL : CRC Press .
   Google Scholar
• Niederer , C and Goss , KU . 2007 . Quantum chemical modeling of humic acid/air equilibrium partitioning of organic vapors . Environ. Sci. Technol. , 41 : 3646 – 3652 .
   PubMed Web of Science ®Google Scholar
• Trout , CC and Kubicki , JD . 2007 . Molecular modeling of Al3+ and benzene interactions with Suwannee fulvic acid . Geochim. Cosmochim. Acta , 71 : 3859 – 3871 .
   Web of Science ®Google Scholar
• Kubicki , JD . 2000 . Molecular mechanics and quantum mechanical modeling of hexane soot and interactions with pyrene . Geochem. Trans. , 7 : 41 – 46 .
   Google Scholar
• Kubicki , JD . 2006 . Molecular simulations of benzene and PAH interactions with soot . Environ. Sci. Technol. , 40 : 2298 – 2303 .
   PubMed Web of Science ®Google Scholar
• Jonker , MTO and Koelmans , AA . 2002 . Sorption of polycyclic aromatic hydrocarbons and polychlorinated biphenyls to soot and soot-like materials in the aqueous environment: Mechanistic considerations . Environ. Sci. Technol. , 36 : 3725 – 3734 .
   PubMed Web of Science ®Google Scholar
• Frenkel , D and Smit , B . 2002 . Understanding Molecular Simulation: From Algorithms To Applications, , 2nd ed , San Diego, CA : Academic Press .
   Google Scholar
• Kollman , P . 1993 . Free-energy calculations—applications to chemical and biochemical phenomena . Chem. Rev. , 93 : 2395 – 2417 .
   Web of Science ®Google Scholar
• Cornell , WD , Cieplak , P , Bayly , CI , Gould , IR , Merz , KM , Ferguson , DM , Spellmeyer , DC , Fox , T , Caldwell , JW and Kollman , PA . 1995 . A second generation force field for the simulation of proteins, nucleic acids, and organic molecules . J. Am. Chem. Soc. , 117 : 5179 – 5197 .
   Web of Science ®Google Scholar
• Akhter , MS , Chughtai , AR and Smith , DM . 1985 . The structure of hexane soot I: Spectroscopic studies . Appl. Spectrosc. , 39 : 143 – 153 .
   Web of Science ®Google Scholar
• Gocken , NA and Reddy , RG . 1996 . Thermodynamics , New York : Plenum Press .
   Google Scholar
• Lybrand , TP . 1990 . “ Computer simulation of biomolecular systems using molecular dynamics and free energy perturbation methods ” . In Reviews in Computational Chemistry , Edited by: Lipkowitz , KB and Boyd , DB . 295 – 321 . New York : VCH .
   Google Scholar
• Cramer , CJ . 2002 . “ Essentials of Computational Chemistry ” . In Theories and Models , New York : Wiley .
   Google Scholar
• 2004 . Hyperchem 7.51 , Gainsville, FL : Hypercube Inc. .
   Google Scholar
• MacKay , D , Shiu , WY and Ma , KC . 1992 . Illustrated Handbook of Physical–Chemical Properties and Environmental Fate for Organic Chemicals , Boca Raton, FL : Lewis Publishers .
   Google Scholar
• International Programme on Chemical Safety . 1998 . “ Selected Non-heterocyclic Polycyclic Aromatic Hydrocarbons ” . In Environmental Health Criteria 202 , Geneva : World Health Organization .
   Google Scholar
• Lide , DR . 2000 . Handbook of Chemistry and Physics , Boca Raton, FL : CRC Press .
   Google Scholar
• Govers , HAJ and De Voogt , P . 1995 . Gas chromatographic derivation of the solubility parameters of polychlorinated biphenyls with the inclusion of cis–trans and optical isomerism and orientational disorder . SAR QSAR Environ. Res. , 3 : 315 – 324 .
   Google Scholar
• Doucette , J-P and Weber , J . 1997 . Computer-aided Molecular Design , London : Academic Press .
   Google Scholar
• 2000 . Prism 3.02 , San Diego, CA : Graphpad Software .
   Google Scholar
• Chickos , JS and Acree , WE . 2003 . Enthalpies of vaporization of organic and organometallic compounds, 1880–2002 . J. Phys. Chem. Ref. Data , 32 : 519 – 878 .
   Web of Science ®Google Scholar
• Van Noort , PCM , Jonker , MTO and Koelmans , AA . 2004 . Modeling maximum adsorption capacities of soot and soot-like materials for PAHs and PCBs . Environ. Sci. Technol. , 38 : 3305 – 3309 .
   PubMed Web of Science ®Google Scholar
• Lohmann , R , MacFarlane , JK and Gschwend , PM . 2005 . Importance of black carbon to sorption of native PAHs, PCBs and PCDDs in Boston and New York harbor sediments . Environ. Sci. Technol. , 39 : 141 – 148 .
   PubMed Web of Science ®Google Scholar
• Hawthorne , SB , Grabanski , CB and Miller , DJ . 2007 . Measured partitioning coefficients for parent and alkyl polycyclic aromatic hydrocarbons in 114 historically contaminated sediments: part 2. Testing the KocKBC two carbon-type model . Environ. Toxicol. Chem. , 26 : 2505 – 2516 .
   PubMed Web of Science ®Google Scholar
• De Maagd , PGJ , Ten Hulscher , DTEM , Van den Heuvel , H , Opperhuizen , A and Sijm , DTHM . 1998 . Physicochemical properties of polycyclic aromatic hydrocarbons: aqueous solubilities, n-octanol/water partition coefficients, and Henry's law constants . Environ. Toxicol. Chem. , 17 : 251 – 257 .
   Web of Science ®Google Scholar
• Van Noort , PCM . 2003 . A thermodynamic-based estimation model for adsorption of organic compounds by carbonaceous materials in environmental sorbents . Environ. Toxicol. Chem. , 22 : 1179 – 1188 .
   PubMed Web of Science ®Google Scholar
• Bergman , DL , Laaksonen , L and Laaksonen , A . 1997 . Visualization of solvation structures in liquid mixtures . J. Mol. Graphics Modell. , 15 : 301 – 306 .
   Google Scholar
• Gustafsson , Ö , Bucheli , TD , Kukulska , Z , Andersson , M , Largeau , C , Rouzaud , JN , Reddy , CM and Eglinton , TI . 2001 . Evaluation of a protocol for the quantification of black carbon in sediments . Global Biogeochem. Cycles , 15 : 881 – 890 .
   Web of Science ®Google Scholar
• Schwarzenbach , RP , Gschwend , PM and Imboden , DM . 2003 . Environmental Organic Chemistry, , 2nd ed , New York : Wiley .
   Google Scholar
• Cornelissen , G , Kukulska , Z , Kalaitzidis , S , Christanis , K and Gustafsson , Ö . 2004 . Relations between environmental black carbon sorption and geochemical sorbent characteristics . Environ. Sci. Technol. , 38 : 3632 – 3640 .
   PubMed Web of Science ®Google Scholar
• Cornelissen , G , Haftka , J , Parsons , J and Gustafsson , Ö . 2005 . Sorption to black carbon of organic compounds with varying polarity and planarity . Environ. Sci. Technol. , 39 : 3688 – 3694 .
   PubMed Web of Science ®Google Scholar