N-octanol-water partition coefficients (log KOW) of 399 congeners of polychlorinated azoxybenzenes (PCAOBs) determined by QSPR- and ANN-based approach

Journal of Environmental Science and Health - Part A Toxic/Hazardous Substances and Environmental Engineering

Volumn 46, Issue 14, 2011, Pages 1748-1762

  Piliszek, Sawomir ^a   Wilczyńska Piliszek, Agata J ^a   Falandysz, Jerzy ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

Bioaccumulation; C t AOBs; Chloro trans azoxybenzenes; Environmental fate; Partition coefficients; PCAOBs; Polychlorinated azoxybenzenes; POPs

Indexed keywords

AZOXYBENZENES; C-T-AOBS; CHLORO TRANS-AZOXYBENZENES; ENVIRONMENTAL FATE; PARTITION COEFFICIENTS; PCAOBS; POPS;

ANOXIC SEDIMENTS; BIOACCUMULATION; BIOCHEMISTRY; CHEMICAL PROPERTIES; HERBICIDES; ROTATION;

C (PROGRAMMING LANGUAGE);

BENZENE DERIVATIVE; OCTANOL; POLYCHLORINATED AZOXYBENZENE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; ARTIFICIAL NEURAL NETWORK; BIOACCUMULATION; COMPUTER PROGRAM; MATHEMATICAL ANALYSIS; PARTITION COEFFICIENT; QUANTITATIVE STRUCTURE PROPERTY RELATION; SEDIMENT; SOIL;

1-OCTANOL; AZO COMPOUNDS; ENVIRONMENTAL POLLUTANTS; HYDROCARBONS, CHLORINATED; NEURAL NETWORKS (COMPUTER); PRINCIPAL COMPONENT ANALYSIS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

TETRA;

EID: 84855801755     PISSN: 10934529     EISSN: 15324117     Source Type: Journal    
DOI: 10.1080/10934529.2011.624001     Document Type: Article

References (69)

1. Hashimoto, S.; Schneider, S.; Morita, M. Levels of 3,3′,4,4- tetrachloroazobenzene in herbicides and bulk reagents. Chemosphere, 1993, 26, 2161-2165. (Pubitemid 23232373)
2. Hill, R.H.; Rollen, Z.J.; Groce, D.F.; Needham, L.L. Tetrachloroazobenzene in 3,4-dichloroaniline and its herbicidal derivatives: Propanil, Diuron, Linuron, and Neburon. Arch. Environ. Health 1981, 36, 11-14. (Pubitemid 11152493)
3. Singh, J.; Bingley, R. Levels of 3,3′,4,4′- tetrachloroazobenzene in propanil herbicide. Bull. Environ. Contam. Toxicol. 1991, 47, 822-826.
4. Bunce, N.J.; Corke, C.T.; Merrick R.L.; Bright, J.H. 3,3′,4, 4′- Tetrachloroazobenzene as a contaminant in commercial propanil. Chemosphere 1979, 8, 283-284. (Pubitemid 9198319)
5. Kearney, P.C.; Plimmer, J.R. Metabolism of 3,4-dichloroaniline in soils. J. Agric. Food Chem. 1972, 20(3), 584-585.
6. Wilczy ńska, A.J.; Puzyn, T.; Piliszek, S.; Falandysz, J. Selection of representative congener for polychlorinated transazobenzenes (PCt-ABs) based on comprehensive thermodynamical and quantum-chemical characterization, J. Environ. Sci. Health Pt. B 2006, 41, 1131-1142. (Pubitemid 44272870)
7. Piliszek, S.; Wilczyńska-Piliszek, A.J.; Puzyn, T.; Falandysz, J. Thermodynamical and quantum-chemical characterization and chemometrical selection of representative congeners of transchloroazoxybenzene. J. Environ. Sci. Health Pt. A 2007, 42, 135-142. (Pubitemid 46018581)
8. Barton, D.; Ollis, W.D. Comprehensive organic chemistry: the synthesis and reactions of organic compounds. Pergamon Press: Oxford; 1979.
9. Poland, A.; Glover, E.; Kende, A.S.; DeCamp,M.; Giandomenico, C.M. 3,4,3′,4′-Tetrachloro azoxybenzene and azobenzene: Potent inducers of aryl hydrocarbon hydroxylase. Science 1976, 194, 627-630.
10. Hsia, M.T.S.; Bairstow, F.V.Z.; Shih, L.C.T.; Pounds, J.G.; Allen, J.R. 3,4,3′,4′-tetrachloroazobenzene: A potential environmental toxicant.Res.Comm. Chem. Pathol. Pharmacol. 1977, 17, 225-236.
11. Nose, K.; Falandysz, J.; Wyrzykowska, B.; Orlikowska, A.; Noma, Y. By-side PCDD/Fs in technical PCB formulations of Kanechlor series. J. Environ. Sci. Health Pt. A 2009, 44, 1528-1537.
12. Vilavert, L.; Nadal, M.;Mari, M.; Schuhmacher,M.; Domingo, J.L. Modification of an environmental survillance program to monitor PCDD/Fs and metals around a municipal solid waste incinerator. J. Environ. Sci. Health Pt. A 2009, 44(13), 1343-1352.
13. Bartha, R.; Pramer, D. Transformation of the herbicide methyl-N- (3,4-dichlorophenyl)-carbamate (Swep) in soil. Bull. Environ. Contam. Toxicol. 1969, 4(4), 240-245.
14. Bartha, R.; Pramer, D. Metabolism of acylanilide herbicides. Adv. Appl. Microbiol. 1970, 13, 317-341.
15. Kaufman, D.D.; Plimmer, J.R.; Iwan, J.; Klingebiel, U.I. 3,3′,4,4′- Tetrachloroazoxybenzene from3,4-dichloroaniline inmicrobial culture. J. Agric. Food Chem. 1972, 20, 916-919.
16. Bordeleau, L.M.; Bartha, R. Azobenzene residues from anilinebased herbicides; evidence for labile intermediates. Bull. Environ. Contam. Toxicol. 1970, 5, 34-37.
17. Kearney, P.C.; Plimmer, J.R.; Guardia, F.B. Mixed chloroazobenzene formation in soil. J. Agr. Food Chem. 1969, 17, 1418-1419.
18. Kearney, P.C.; Smith,R.J., Jr.; Plimmer, J.R.; Guardia,F.S. Propanil and TCAB residues in rice soils. Weed Sci. 1970, 18, 464-466.
19. Sprott, G.D.; Corke, C.T. Formation of 3,3′,4,4′- tetrachloroazobenzene from 3,4-dichloroaniline in Ontario soils. Can. J. Microbiol. 1971, 17, 235-240.
20. NTP, National Toxicology Program. Executive summary of safety and toxicity information 3,3′,4,4′-tetrachloroazobenzene, 3,3′,4,4′- tetrachloroazoxybenzene. National Institute of Health, Research Triangle Park, NC; 1991.
21. Wania, F.; Mackay, D. Tracking the distribution of persistent organic pollutants. Environ. Sci. Technol. 1996, 30, 390A-396A. (Pubitemid 27127765)
22. Puzyn, J.; Falandysz, J. Octanol/water partition coefficients of chloronaphthalenes. J. Environ. Sci. Health Pt. A 2005, 40(14), 1651-1663. (Pubitemid 41176841)
23. Falandysz, J.; Puzyn, T.; Szymanowska, B.; Kawano, M.; Markuszewski, M.; Kaliszan, R.; Skurski, O.; B?a?zejowski, J.; Wakimoto, T. Thermodynamic and physico-chemical descriptors of chloronaphthalenes: an attempt to select features explaining environmental behavior and specific toxic effects of these compounds. Pol. J. Environ. Stud. 2001, 10 (4), 217-235. (Pubitemid 33680672)
24. Puzyn, T.; Falandysz, J. QSPR modeling of partition coefficients and Henry's Law constants for 75 chloronaphthalene congeners by means of six chemometrical approaches-a comparative study. J. Phys. Chem. Ref. Data 2007, 36 (1), 203-214.
25. Puzyn, T.; Falandysz, J. Computational estimation of logarithm of n-octanol/air partition coefficient and subcooled vapour pressures of 75 chloronaphthalene congeners. Atmos. Environ. 2005, 39, 1439-1446.
26. Puzyn, T.; Rostkowski, P.; Świeczkowski A. Jȩdrusiak, A.; Falandysz, J. Prediction of environmental partition coefficients and the Henry's law constans for 135 congeners of chlorodibenzothiophene. Chemosphere 2006, 62, 1817-1828. (Pubitemid 43374919)
27. Brown, A.; Olivero, J.; Holdan, W.; Ganey, P. Neutrophil activation by polychlorinated biphenyls: structure-activity relationships. Toxicol. Sci. 1998, 46, 308-316. (Pubitemid 29069615)
28. Rayne, S.; Forest, K. A new class of perfluorinated acid contaminants: Primary and secondary substituted perfluoroalkyl sulfonamides are acidic at environmentally and toxicologically relevant pH values. J. Environ. Sci. Health Pt. A 2009, 44(13), 1388-1399.
29. Rayne, S.; Forest, K. Congener-specific organic carbon-normalized soil and sediment-water partitioning coefficients for the C1 through C8 perfluoroalkyl carboxylic and sulfonic acids. J. Environ. Sci. Health Pt. A 2009, 44(13), 1374-1387.
30. Rayne, S.; Forest, K. Quantitative structure-activity relationship (QSAR) studies for predicting activation of the ryanodine receptor type 1 channel complex (RyR1) by polychlorinated biphenyl (PCB) congeners. J. Environ. Sci. Health Pt. A 2010, 45(3) 355-362.
31. Rayne, S.;Forest, K. Modeling the hydrolysis of perfluorinated compounds containing carboxylic and phosphoric acid ester functions and sulfonamide groups. J. Environ. Sci. Health Pt. A 2010, 45(4) 432-446.
32. Rayne, S.; Forest, K. pKa values of the monohydroxylated polychlorinated biphenyls (OH-PCBs), polybrominated biphenyls (OHPBBs), polychlorinated diphenyl ethers (OH-PCDEs), and polybrominated diphenyl ethers (OH-PBDEs). J. Environ. Sci. Health Pt. A 2010, 45(11), 1322-1346.
33. Rayne, S.; Forest, K. Dow and Kaw,eff vs. Kow and K?aw: Acid/base ionization effects on partitioning properties and screening commercial chemicals for long-range transport and bioaccumulation potential. J. Environ. Sci. Health Pt. A 2010, 45(12) 1550-1594.
34. Alparone, A.; Librando, V.;Minniti, Z. Validation of semiempirical PM6method for the prediction of molecular properties of polycyclic aromatic hydrocarbons and fullerenes. Chem. Phys. Lett. 2008, 460, 151-154.
35. Alparone, A.; Librando, V. Electronic dipole polarizabilities of polychlorinated dibenzofurans and semiempirical PM6 level performance. J. Mol. Str. Theochem. 2009, 894, 128.
36. Wilczyńska-Piliszek, A.; Piliszek, S.; Falandysz, J. Use of quantitative-structure property relationship (QSPR) and artificial neural network (ANN) based approaches for estimating the octanol-water partition coefficients of the 209 chlorinated transazobenzene congeners. J. Environ. Sci. Health Pt. B 2011, 47, DOI 10.1080/03601234.2011.616779
37. http://www.gaussian.com/gtech/gur/mbasissets.htm.
38. StatSoft. Elektroniczny podrȩcznik statystyki PL. Kraków, 2006; http://www.statsoft.pl/textbook/stathome.html.
39. Statistica neural network PL, Kurs uzytkowania programu na przyk?adach. StatSoft Polska Sp. z o.o.: Kraków, 2001.
40. http://www.cmbi.ru.nl/molden/.
41. http://www.brothersoft.com/acd-chemsketch-133131.html.
42. McLean, A.D.; Chandler, G.S. Contracted Gaussian-basis sets for molecular calculations. 1. 2nd row atoms, Z=11-18. J. Chem. Phys. 1980, 72, 5639-5648.
43. Raghavachari, K.; Binkley, J.S.; Seeger, R.; Pople, J.A. Selfconsistent molecular orbital methods. 20. Basis set for correlated wave-functions. J. Chem. Phys. 1980, 72, 650-654.
44. Blaudeau, J.-P.; McGrath, M. P.; Curtiss, L. A.; Radom, L. Extension of Gaussian-2 (G2) theory to molecules containing third-row atoms K and Ca. J. Chem. Phys. 1997, 107, 5016-5021. (Pubitemid 127560673)
45. Wachters, J.H. Gaussian basis set for molecular wavefunctions containing third-row atoms. J. Chem. Phys. 1970, 52, 1033.
46. Hay, P.J. Gaussian basis sets for molecular calculations - representation of 3D orbitals in transition-metal atoms. J. Chem. Phys. 1977, 66, 4377-4384.
47. Raghavachari, K.; Trucks, G.W. Highly correlated systems: Excitation energies of first row transition metals Sc-Cu. J. Chem. Phys. 1989, 91, 1062-1065.
48. Binning R.C. Jr.; Curtiss, L.A. Compact contracted basis-sets for 3rd-row atoms - GA-KR. J. Comp. Chem. 1990, 11, 1206-1216.
49. McGrath, M.P.;Radom, L. Extension ofGaussian-1 (G1) theory to bromine-containing molecules. J. Chem. Phys. 1991, 94, 511-516.
50. Curtiss, L.A.; McGrath, M.P.; Blaudeau, J.-P.;Davis,N.E.; Binning R.C. Jr.; Radom, L. Extension of Gaussian-2 theory to molecules containing third-row atoms Ga-Kr. J. Chem. Phys. 1995, 103, 6104-6113.
51. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A.; Vreven, Jr.T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Knox, X.; Li, J.E.; Hratchian, H.P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.;Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.;Ortiz, J.V.;Cui,Q.; Baboul,A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu,G.; Liashenko, A.; Piskorz, P.;Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C.; Pople, J.A. Gaussion 03, Gaussian, Inc., Pittsburgh PA; 2003.
52. MOPAC. Version 1.0, J.J.P. Stewart, Fujitsu Limited, Tokyo, Japan; 2006.
53. Rocha,G.B.; Freire, R.O.; Sima, A.M.; Stewart, J.J.P. RM1: A reparameterization ofAM1for H, C,N,O, P, S, F, Cl, Br, and I. J. Comp. Chem. 2006, 27(10), 1101-1111. (Pubitemid 43989803)
54. http://www.rm1.sparkle.pro.br/rm1-software/mopac2009.
55. Stewart, J.J.P. Optimization of parameters for semiempirical methods V: Modification of NDDO approximations and application to 70 elements. J. Mol. Mod. 2007, 13, 1173-1213. (Pubitemid 47629446)
56. Burstein, K.Y.; Isaew, A.N. MNDO calculations on hydrogen bonds. Modified function for core-core repulsion. Theor. Chim. Acta 1984, 64, 397-401.
57. Tomasi, J.; Persico, M. Molecular interactions in solution: An overview of methods based on continuous distributions of the solvent. Chem. Rev. 1994, 94, 2027-2094. (Pubitemid 124000195)
58. Stasicka, Z.; Achmatowicz, O. Kompendium terminologii chemicznej. ZamKor; 2005.
59. Jaworski, B.M.; Dietlaf, A.A. Fizyka poradnik encyklopedyczny. Wydawnictwo Naukowe PWN: Warszawa; 1995.
60. Stewart, J.J.P. "MOPAC" Stewart Computational Chemistry, Colorado Springs, CO, USA, http://OpenMOPAC.net.
61. Morrisom, R.T.; Boyd, R.N. Chemia organiczna, tom 1. Państwowe Wydawnictwo Naukowe: Warszawa; 1998.
62. Todeschini, R.; Consonni, V. Handbook of Molecular Descriptors, vol. 11. Weinheim: Wiley-VCH; 2000.
63. Rice, S.A. Advances in Chemical Physics. New York: Wiley-IEEE; 2005.
64. Yang, W.; Parr, R.G. Hardness, softness, and the fuki function in the electronic theory of metals and catalysis. Proc. Nat. Acad. Sci. USA 1985, 82, 6723-6726.
65. Ochterski, J.W. Thermochemistry in Gaussian. www.gaussian.com; 2000.
66. Zhan, C.-G.; Nichols, J.A.; Dixon, D.A. Ionization potential, electron affinity, electronegativity, hardness, and electron exciation energy: molecular properties from density functional theory orbital energies. J. Phys. Chem. A. 2003, 107(20), 4184-4195.
67. Pigoń, K.; Ruziewicz, Z. Chemia fizyczna. Państwowe Wydawnictwo Naukowe: Warszawa; 1980.
68. Aczel, A.D. Statystyka w zarza̧dzaniu. Wydawnictwo Naukowe PWN: Warszawa; 2006.
69. Wyrzykowska, B.; Szymczyk, K.; Ichihashi, H.; Falandysz, J.; Yamasaki, S. Application of HR/ICP/MS and principal component analysis for studying interdependences among 23 trace elements in Polish beers. J. Agric. Food Chem. 2001, 49 (7) 3425-3431 (Pubitemid 32845079)