SAR/QSAR approaches to solubility, partitioning and sorption of phthalates

Chemosphere

Volumn 38, Issue 11, 1999, Pages 2613-2624

  Thomsen, Marianne ^a   Rasmussen, Angélique G ^a   Carlsen, Lars ^a  

^a NATIONAL ENVIRONMENTAL RESEARCH INSTITUTE   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ENVIRONMENTAL CHEMICAL; ESTER DERIVATIVE; OCTANOL; PHTHALIC ACID; PHTHALIC ACID ESTER; WATER; XENOBIOTIC AGENT;

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; ELECTROCHEMISTRY; HYDROPHOBICITY; MOLECULAR SIZE; PARTITION COEFFICIENT; PHYSICAL PARAMETERS; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

EID: 0033136621     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0045-6535(98)00469-X     Document Type: Article

References (46)

1. Bahnick, D.A., Doucette, W.J. (1988): Use of molecular connetivity indices to estimate soil sorption coefficients for organic chemicals. Chemosphere 17, 1703-1715.
2. Bersuker, I.B., Dimoglo, A.S. (1991): The electron-topological approach to the QSAR problem. In: Reviewss of Computational Chemistry. (Eds: Boyd, Donald; Lipkowitz, Ken) VCH publishers.
3. Bintein, S., Devillers, J. (1994): QSAR for organic chemical sorption in soils and sediments. Chemosphere 28, 1171-1188 .
4. Bonchev, D., Kier, L.B., Hall, N.L. (1990): Computational Chemical Graph Theory. 1. ed. Nova Science Publishers, Inc., NY. 331 pages.
5. Brusseau, M.L. (1993): Using QSAR to evaluate phenomenological models for sorption of organic compounds by soil. Environmental Toxicology and Chemistry 12, 1835-1846.
6. Chen, F., Hollen-Andersen, J., Tyle, H. (1993): New developments of the UNTFAC model for environmental application. Chemosphere 26, 1325-1354.
7. Defoe, D.L., Holcombe, G.W., Hammermeister, D.E. (1990): Solubility and toxicity of eight phthalate esters to four aquatic organisms, Environ. Tox. Chem. 9, 623-636.
8. Hall, L.H., Mohney, B., Kier, L.B. (1991a): The electropological state: Structure information at the atomic level for molecular graphs. J. Chem. Inf. Comput. Sci. 31, 76-82.
9. Hall, L.H., Dailey, R.S., Kier, L.B. (1993): Design of molecules from quantitative structure-activity relationship models. 3. Role of higher order path counts: Path 3. J. Chem. Inf. Comput. Sci. 33, 598-603.
10. Hall, L.H., Mohney, B., Kier, L.B. (1991b): The Electropological State:; An Atom Index for QSAR. QSAR 10, 43-51.
11. Hall, L.H., Kier, L.B. (1995): Electropological state indices for atom types: A novel combination of electronic, topological, and valens state information. J. Chem. Inf. Comput. Sci. 35, 1039-1045.
12. Hall, L.H., Kier, L.B. (1991): The molecular connectivity chi indexes in structure-property modeling. In: Reviews in Computational Chemistry. Vol. 2. (Eds: Lipkowitz, Kenny B; Boyd, Donald B) VCH publishers, NY, 515.
13. Hansch, C., Quinlan, J.E., Lawrence, G.L. (1968): The LFER between partition coefficients and the aqueous solubility of organic liquids. J. Org. Chem. 33, 347-350.
14. Hansen, H.K., Rasmussen, P., Fredenslund, A.A., Schiller, M., Gmehling, J. (1991): Vapor-liquid equibrilia by UNIFAC group contributions 5. Revision and extension. Ind. Eng. Chem. Res. 30, 2352-2355.
15. Hu, Q., Wang, X., Brusseau, M.L. (1995): Quantitative structure-activity relationships for evaluating the influence of sorbate structure on sorption of organic compounds by soil. Environmental Toxicology and Chemistry 14, 1133-1140.
16. Kaliszan, R., Lamparczyk, H. (1978): A relationship between the connetivity indicies and retention indicies of polycyclic aromatic hydrocarbons. J. Chrom. Sci. 16, 246-248.
17. Kan, A.T., Tomson, M.B. (1996): UNIFAC prediction of aqueous and nonaqueous solubilities of chemicals with environmental interest. Environ. Sci. Technol. 30, 1369-1376.
18. Karickhoff, S.W. (1981): Semi-empirical estimation of sorption of hydrophobic pollutants on naturel sediments and soils. Chemosphere 10, 833-846.
19. Kier, L.B., Hall, L.H. (1985): Molecular connectivity in structure-activity analysis. Chemometric Series, 1'st Ed. Vol. 9. Research Studies Press LTD., England. 262 pages.
20. Kier, L.B., Hall, L.H. (1976): Molecular Connectivity in Chemistry and Drug Research, Vol 14. Academic Press, NY. 257 pages.
21. Kier, L.B., Hall, L.H. (1990a): The molecular connectivity of non-sigma electrons. Rep. Mol. Theory 1, 121-125.
22. Kier, L.B., Hall, L.H., Frazer, J.W. (1991): An index of electropological state for atoms in molecules. J. Math. Chem. 7, 229-241.
23. Kier, L.B., Hall, L.H. (1990b): An electropological-state index for atoms in molecules. Pharmaceutical Research 7 no.8, 801-807.
24. Kier, L.B., Hall, L.H. (1997): The E-state as an extended free valence. J. Chem. Inf. Comput. Sci. 37, 548-552.
25. Kier, L.B., Hall, L.H. (1981): Derivation and significance of valence molecular connectivity. J. Pharm. Sci. 70, 583-589.
26. Leyder, F., Boulanger, P. (1983): Ultraviolet absorption, aqueous solubility, and octanol-water partition for several phthalates, Bull. Environ. Contam. Toxicol. 30, 152-157.
27. Lipkowitz, K.B., Boyd, D.B. (eds.) (1990): Reviews in Computational Chemistry. 1st Ed. VCH, NY. 419 pages.
28. Meylan, W., Howard, P.H. (1992): Molecular topology/fragtment contribution method for predicting soil sorption coefficients. Environm. Sci. and Technol. 26, 1560-1567.
29. Miller, M.M., Wasik, S.P., Huang, G.-L., Shiu, W.-Y., Mackay, D. (1985): Relationship between octanol-water coeffficient and aqueous solubility. Environm. Sci. and Technol. 19, 522-529.
30. Nielsen, E., Larsen, P.B. (1996): Texicological evaluation and limit values for DEHP and phthalates, other than DEHP. Environmental Review No. 6, Danish Environmental Protection Agency
31. Nordic Council of Ministers (1996): Chemicals with estrogen-like effects, TemaNord 1996:580.
32. Pedersen, F., Larsen, J. (1996): Review of Environmental Fate and Effects of Di(2-ethylhexyl)phthalate. Working Report. No. 54, Danish Environmental Protection Agency.
33. Rasmussen, A.G. (1998): Prediction of aqueous solubilities and octanol-water coefficients of phthtalates by the UNIFAC group contribution method. NERI Research Notes No. 69, National Environmental Research Institute.
34. Sabljic, A. (1987): On the prediction of soil sorption coefficients of organic pollutants from molecular structure: Application of molecular topology model. Environm. Sci. and Technol. 21, 358-366.
35. Sabljic, A., Protic, M. (1982): Relationship between molecular connetivity indices and soil sorption coefficients of polycyclic aromatic hydrocarbons. Bull. Environm. Contam. Toxicol. 28, 162-165.
36. Sabljic, A. (1984): Predictions of the nature and strength of soil sorption of organic pollutants by molecular topology. J. Agri. Food Chem. 32, 243-246.
37. Staples, C.A., Peterson, D.R., Parkerton, T.F., Adams, W.J. (1997): The environmental fate of the phthalates esters: A litterature review, Chemosphere, 35, 667-749.
38. Thomsen, M., Carlsen, L. (1998): Phthalater i miljøet. Opløselighed, Sorption og Transport. Department of Environmental Chemistry, NERI technical report in press.
39. Thomsen, M., Hvidt, S., Carlsen, L. (subm.): Solubility of phthalates revisited. Environmental Implications, Quantitative Structure-activity Relationships in Environmenal Sciences -VIII, submitted for publication.
40. Toppari, J., Larsen, J.C., Christiansen, P., Giwercman, A., Grandjean, P., Gulillette, L.J. Jr., Jégou, B., Jensen, T.K., Jounannet, P., Keiding, N., Leffers, H., McLachlan, J.A., Meyer, O., Müller, J., Meyts, E.R., Scheike, T., Sharpe, R., Sumpter, J., Skakkebæk, N.E. (1995): Male Reproductive Health and Environmental Chemicals with Estrogenic Effects. Miljøprojekt No. 290, Danish Environmental Protection Agency.
41. Wershaw, R.L. (1986): A new model for humic materials and their interactions with hydrophobic organic chemicals in soil-water or sediment-water systems. J. Contam. Hydrol., 1, 29-45.
42. Vikelsøe, J., Thomsen, M., Johansen, E., Carlsen, L. (1998), National Environmental Research Institute, Department of Environmental Chemistry: Fate of Phthalate and Nonylphenols in Soil. Field Study of Soil Depth Profiles. NERI technical report in press.
43. Wolfe, N.L., Burns, L.A., Steen, W.C. (1980a): Use of linear free energy relationships and evaluative model to asses the fate and transport of phthalate esters in the aquatic environment. Chemosphere 9, 393-402.
44. Wolfe, N.L., Steen, W.C., Burns, L.A. (1980b): Phthalate ester hydrolysis:Linear free energy relationships. Chemosphere 9, 403-408.
45. Woodburn, K.B., Rao, P.S.C., Fukui, M., Nkedi-Kizza, P. (1986): Solvophobic approach for predicting sorption og hydrophobic organic chemicals on synthetic sorbents and soils. J. Contam. Hydrol. 1, 227-241.
46. Yalkawsky, S.H., Valvani, S.C. (1979): Solubilities and partitioning 2. Relationships between aquous solubilities, partition coefficients, and molecular surface areas of rigid aromatic hydrocarbons. Journal of Chemical and Engineering Data 24, 127-129.