Molecular simulation of polycyclic aromatic hydrocarbon sorption to black carbon

SAR and QSAR in Environmental Research

Volumn 20, Issue 3-4, 2009, Pages 221-240

  Haftka, J J H ^a   Parsons, J R ^a   Govers, H A J ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Free energy; Molecular simulation; Monte Carlo; PAH; Statistical mechanics

Indexed keywords

BIOREMEDIATION; CARBON; CONTAMINATION; FREE ENERGY; IMPURITIES; MONTE CARLO METHODS; SEDIMENTS; SOIL POLLUTION; SOOT; STATISTICAL MECHANICS;

BIOREMEDIATION POTENTIALS; BLACK CARBON; CONTAMINATED SOILS; ENVIRONMENTAL PROCESS; EXPERIMENTAL VALUES; FREE-ENERGY DIFFERENCE; HYDROPHOBIC ORGANIC CONTAMINANT; MOLECULAR SIMULATIONS; MONTE CARLO; SORPTION COEFFICIENTS;

POLYCYCLIC AROMATIC HYDROCARBONS;

CHARCOAL; POLYCYCLIC AROMATIC HYDROCARBON;

ADSORPTION; ARTICLE; CHEMISTRY; COMPUTER SIMULATION; MONTE CARLO METHOD; STATISTICAL MODEL;

ADSORPTION; CHARCOAL; COMPUTER SIMULATION; MODELS, STATISTICAL; MONTE CARLO METHOD; POLYCYCLIC HYDROCARBONS, AROMATIC;

EID: 67949105087     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/10629360902949336     Document Type: Article

References (42)

1. H.A.J. Govers, H.B. Krop, J.R. Parsons, T. Tambach, and J.D. Kubicki, Dissolved organic carbon-contaminant interaction descriptors found by 3D force field calculations, SAR QSAR Environ. Res. 13 (2002), pp. 271-280.
2. H.A.J. Govers, A. Van Roon, and J.R. Parsons, Calculation of the interaction between dissolved organic carbon and organic micropollutants by three dimensional force field methods, Environ. Toxicol. Chem. 22 (2003), pp. 753-759.
3. H.A.J. Govers, P. De Voogt, O. Kwast, and E.A.J. Bleeker, Membrane-contaminant interaction found by 3D force field calculations, SAR QSAR Environ. Res. 13 (2002), pp. 135-;143.
4. A. Van Roon, J.R. Parsons, and H.A.J. Govers, Cytochrome P450cam-monoterpene interactions. Prediction of product profiles for monoterpene hydroxylation using a calibrated 3D force field, SAR QSAR Environ. Res. 16 (2005), pp. 369-384.
5. T.D. Bucheli and O. Gustafsson, Quantification of the soot-water distribution coefficient of PAHs provides mechanistic basis for enhanced sorption observations, Environ. Sci. Technol. 34 (2000), pp. 5144-5151.
6. G. Cornelissen, O. Gustafsson, T.D. Bucheli, M.T.O. Jonker, A.A. Koelmans, and P.C.M. Van Noort, 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 (2005), pp. 6881-6895.
7. A.A. Koelmans, M.T.O. Jonker, G. Cornelissen, T.D. Bucheli, P.C.M. Van Noort, and O. Gustafsson, Black carbon: the reverse of its dark side, Chemosphere 63 (2006), pp. 365-377.
8. J.D. Kubicki and S.E. Apitz, Models of natural organic matter and interactions with organic contaminants, Org. Geochem. 30 (1999), pp. 911-927.
9. H.-R. Schulten, Interactions of dissolved organic matter with xenobiotic compounds: molecular modeling in water, Environ. Toxicol. Chem. 18 (1999), pp. 1643-1655.
10. M.S. Diallo, J.-L. Faulon, W.A. Goddard III, and J.H. Johnson Jr, 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, E.A. Ghabbour and G. Davies, eds., The Royal Society of Chemistry, Cambridge, 2001, pp. 221-237.
11. H.-R. Schulten, M. Thomsen, and L. Carlsen, Humic complexes of diethyl phthalate: molecular modelling of the sorption process, Chemosphere 45 (2001), pp. 357-369.
12. J.D. Kubicki and C.C. Trout, Molecular modeling of fulvic and humic acids: charging effects and interactions with Al3{thorn}, benzene, and pyridine, in Geochemical and hydrological reactivity of heavy metals in soils, W.L. Kingery and H.M. Selim, eds., CRC Press, Boca Raton, FL, 2003, pp. 113-143.
13. C. Niederer and K.U. Goss, Quantum chemical modeling of humic acid/air equilibrium partitioning of organic vapors, Environ. Sci. Technol. 41 (2007), pp. 3646-3652.
14. C.C. Trout and J.D. Kubicki, Molecular modeling of Al3+ and benzene interactions with Suwannee fulvic acid, Geochim. Cosmochim. Acta 71 (2007), pp. 3859-3871.
15. J.D. Kubicki, Molecular mechanics and quantum mechanical modeling of hexane soot and interactions with pyrene, Geochem. Trans. 7 (2000), pp. 41-46.
16. J.D. Kubicki, Molecular simulations of benzene and PAH interactions with soot, Environ. Sci. Technol. 40 (2006), pp. 2298-2303.
17. M.T.O. Jonker and A.A. Koelmans, Sorption of polycyclic aromatic hydrocarbons and polychlorinated biphenyls to soot and soot-like materials in the aqueous environment: Mechanistic considerations, Environ. Sci. Technol. 36 (2002), pp. 3725-3734.
18. D. Frenkel and B. Smit, Understanding Molecular Simulation: From Algorithms To Applications, 2nd ed., Academic Press, San Diego, CA, 2002.
19. P. Kollman, Free-energy calculations-applications to chemical and biochemical phenomena, Chem. Rev. 93 (1993), pp. 2395-2417.
20. W.D. Cornell, P. Cieplak, C.I. Bayly, I.R. Gould, K.M. Merz, D.M. Ferguson, D.C. Spellmeyer, T. Fox, J.W. Caldwell, and P.A. Kollman, A second generation force field for the simulation of proteins, nucleic acids, and organic molecules, J. Am. Chem. Soc. 117 (1995), pp. 5179-5197.
21. M.S. Akhter, A.R. Chughtai, and D.M. Smith, The structure of hexane soot I: Spectroscopic studies, Appl. Spectrosc. 39 (1985), pp. 143-153.
22. N.A. Gocken and R.G. Reddy, Thermodynamics, Plenum Press, New York, 1996.
23. T.P. Lybrand, Computer simulation of biomolecular systems using molecular dynamics and free energy perturbation methods, in Reviews in Computational Chemistry, K.B. Lipkowitz and D.B. Boyd, eds., VCH, New York, 1990, pp. 295-321.
24. C.J. Cramer, Essentials of Computational Chemistry, Theories and Models, Wiley, New York, 2002.
25. Hyperchem 7.51, Hypercube Inc., Gainsville, FL, 2004.
26. D. MacKay, W.Y. Shiu, and K.C. Ma, Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, Lewis Publishers, Boca Raton, FL, 1992.
27. International Programme on Chemical Safety, Selected Non-heterocyclic Polycyclic Aromatic Hydrocarbons, Environmental Health Criteria 202, World Health Organization, Geneva, 1998.
28. D.R. Lide, Handbook of Chemistry and Physics, CRC Press, Boca Raton, FL, 2000.
29. H.A.J. Govers and P. De Voogt, 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 (1995), pp. 315-324.
30. J.-P. Doucette and J. Weber, Computer-aided Molecular Design, Academic Press, London, 1997.
31. Prism 3.02, Graphpad Software, San Diego, CA, 2000.
32. J.S. Chickos and W.E. Acree, Enthalpies of vaporization of organic and organometallic compounds, 1880-2002, J. Phys. Chem. Ref. Data 32 (2003), pp. 519-878.
33. P.C.M. Van Noort, M.T.O. Jonker, and A.A. Koelmans, Modeling maximum adsorption capacities of soot and soot-like materials for PAHs and PCBs, Environ. Sci. Technol. 38 (2004), pp. 3305-3309.
34. R. Lohmann, J.K. MacFarlane, and P.M. Gschwend, Importance of black carbon to sorption of native PAHs, PCBs and PCDDs in Boston and New York harbor sediments, Environ. Sci. Technol. 39 (2005), pp. 141-148.
35. S.B. Hawthorne, C.B. Grabanski, and D.J. Miller, 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 (2007), pp. 2505-2516.
36. P.G.J. De Maagd, D.T.E.M. Ten Hulscher, H. Van den Heuvel, A. Opperhuizen, and D.T.H.M. Sijm, Physicochemical properties of polycyclic aromatic hydrocarbons: aqueous solubilities, n-octanol/water partition coefficients, and Henry's law constants, Environ. Toxicol. Chem. 17 (1998), pp. 251-257.
37. P.C.M. Van Noort, A thermodynamic-based estimation model for adsorption of organic compounds by carbonaceous materials in environmental sorbents, Environ. Toxicol. Chem. 22 (2003), pp. 1179-1188.
38. D.L. Bergman, L. Laaksonen, and A. Laaksonen, Visualization of solvation structures in liquid mixtures, J. Mol. Graphics Modell. 15 (1997), pp. 301-306.
39. O. Gustafsson, T.D. Bucheli, Z. Kukulska, M. Andersson, C. Largeau, J.N. Rouzaud, C.M. Reddy, and T.I. Eglinton, Evaluation of a protocol for the quantification of black carbon in sediments, Global Biogeochem. Cycles 15 (2001), pp. 881-890.
40. R.P. Schwarzenbach, P.M. Gschwend, and D.M. Imboden, Environmental Organic Chemistry, 2nd ed., Wiley, New York, 2003.
41. G. Cornelissen, Z. Kukulska, S. Kalaitzidis, K. Christanis, and O. Gustafsson, Relations between environmental black carbon sorption and geochemical sorbent characteristics, Environ. Sci. Technol. 38 (2004), pp. 3632-3640.
42. G. Cornelissen, J. Haftka, J. Parsons, and O. Gustafsson, Sorption to black carbon of organic compounds with varying polarity and planarity, Environ. Sci. Technol. 39 (2005), pp. 3688-3694.