Prediction of subcooled vapor pressures (log P_L) of 399 polychlorinated trans-azoxybenzenes by using the QSPR and ANN approach

References

• Loganatham , B. G. “ Global contamination trends of persistent chemicals: An Overview ” . In Global Contamination Trends of Persistent Chemicals , Edited by: Loganathan , B. G. and Lam , P. K.S. 3 – 29 . Boca Raton , , Florida, USA : CRC Press .
   Google Scholar
• Banaszkiewicz , T. 2003 . Chemiczne środki ochrony roślin, zagadnienia ogólne. Wyd , Olsztyn : Uniwersytetu Warmińsko-Mazurskiego .
   Google Scholar
• Bunce , N. J. , Corke , C. T. , Merrick , R. L. and Bright , J. H. 1979 . 3,3′,4,4′-Tetrachloroazobenzene as a contaminant in commercial propanil . Chemosphere , 8 : 283 – 284 .
   Web of Science ®Google Scholar
• Hashimoto , S. , Schneider , S. and Morita , M. 1993 . Levels of 3,3′,4,4-tetrachloroazobenzene in herbicides and bulk reagents . Chemosphere , 26 : 2161 – 2165 .
   Web of Science ®Google Scholar
• Hill , R. H. , Rollen , Z. J. , Groce , D. F. and Needham , L. L. 1981 . Tetrachloroazobenzene in 3,4-dichloroaniline and its herbicidal derivatives: Propanil, Diuron, Linuron, and Neburon . Arch. Environ. Health , 36 : 11 – 14 .
   PubMed Web of Science ®Google Scholar
• NTP. National Toxicology Program . 1991 . Executive summary of safety and toxicity information 3,3′,4,4′-tetrachloroazobenzene, 3,3′,4,4′-tetrachloroazoxybenzene , Research Triangle Park , NC : National Institutes of Health .
   Google Scholar
• Pillai , U. A. , Ziegler , T. L. , Wang , D. X. , Kattnig , M. J. , McClure , T. , Liebler , D. C. , Mayersohn , M. and Sipes , I. G. 1996 . 3,3′,4,4′-Tetrachloroazobenzene absorption, disposition, and metabolism in male Fischer 344 rats . Drug Metabol. Disp. , 24 : 238 – 244 .
   PubMed Web of Science ®Google Scholar
• Poland , A. , Glover , E. , Kende , A. S. , DeCamp , M. and Giandomenico , C. M. 1976 . 3,4,3′,4′-Tetrachloro azoxybenzene and azobenzene: Potent inducers of aryl hydrocarbon hydroxylase . Science , 194 : 627 – 630 .
   PubMed Web of Science ®Google Scholar
• United States Environmental Protection Agency (USEPA) . 1985 . Health and Environmental Effects Profile for TCAB, TCAOB and TCHB. Environmental Criteria and Assessment Office, Office of Health and Environmental Assessment, Office of Research and Development, U.S , OH : Environmental Protection Agency, Cincinati . EPA/600/X-85/394
   Google Scholar
• Piliszek , S. , Wilczyńska-Piliszek , A. J. , Puzyn , T. and Falandysz , J. 2007 . Thermodynamical and quantum-chemical characterization and chemometrical selection of representative congeners of trans-chloroazoxybenzene . J. Environ. Sci. Health Part A , 42 : 135 – 142 .
   Web of Science ®Google Scholar
• Barton , D. and Ollis , W. D. 1979 . Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds , Oxford : Pergamon Press .
   Google Scholar
• Wilczyńska , A. J. , Puzyn , T. , Piliszek , S. and Falandysz , J. 2006 . Selection of representative congener for polychlorinated trans-azobenzenes (PCt-ABs) based on comprehensive thermodynamical and quantum-chemical characterization . J. Environ. Sci. Health Part B , 41 : 1131 – 1142 .
   PubMed Web of Science ®Google Scholar
• Falandysz , J. , Brudnowska , B. , Kawano , M. and Wakimoto , T. 2001 . Polychlorinated biphenyls and organochlorine pesticides in soils from the southern part of Poland . Arch. Environ. Contam. Toxicol. , 40 : 173 – 178 .
   PubMed Web of Science ®Google Scholar
• Sadi , B. B. and Loganathan , B. “ Temporal trends of selected chlorinated hydrocarbon pollutants in sediments of Kentucky Lake ” . In Global Contamination Trends of Persistent Chemicals , Edited by: Loganathan , B. G. and Lam , P. K.S. 477 – 490 . Boca Raton , , FL, USA : CRC Press .
   Google Scholar
• Bartha , R. and Pramer , D. 1969 . Transformation of the herbicide methyl-N-(3,4-dichlorophenyl)-carbamate (Swep) in soil . Bull. Environm. Contam. Toxicol. , 4 ( 4 ) : 240 – 245 .
   PubMed Web of Science ®Google Scholar
• Burant , C. F. and Hsia , M. T.S. 1984 . Excretion and distribution of two occupational toxicants, tetrachloroazobenzene and tertrachloroazoxy benzene in the rat . Toxicology , 29 : 243 – 250 .
   Google Scholar
• Kaufman , D. D. , Plimmer , J. R. , Iwan , J. and Klingebiel , U. I. 1972 . 3,3′,4,4′-Tetrachloroazoxybenzene from 3,4-dichloroaniline in microbial culture . J. Agric. Food Chem. , 20 : 916 – 919 .
   Web of Science ®Google Scholar
• Mansour , M. , Parlar , H. and Korte , F. 1975 . Beiträge zur Ökologischen Chemi Ci: Reaktionsverhalten von 3,4 Dichloranilin und 3,4 Dichlorphenol in Lösung, als Festkörper und in der Gasphase bei UV-Bestrahlung . Chemosphere , 4 : 235 – 240 . 1975
   Google Scholar
• Miller , G. C. , Zisook , R. and Zepp , R. 1980 . Photolysis of 3,4-dichloroaniline in natural waters . J. Agric. Food Chem. , 28 : 1053 – 1056 .
   Web of Science ®Google Scholar
• Poland , A. and Knutson , J. C. 1982 . 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: Examination of the mechanism of toxicity . Ann. Rev. Pharm. Toxicol. , 22 : 517 – 554 .
   PubMed Web of Science ®Google Scholar
• Allison , M. and Morita , M. 1995 . Bioaccumulation and toxic effects of elevated levels of 3,3′,4,4′-tetrachloroazobenzene (3,3′,4,4′-TCAB) towards aquatic organisms. III: Bioaccumulation and toxic effects of detrital 3,3′,4,4′-TCAB on the aquatic snail, Indohiramakigai (Indoplanorbis exustus) . Chemosphere , 30 : 233 – 242 .
   PubMed Web of Science ®Google Scholar
• Worebey , B. L. 1984 . Fate of 3,3′,4,4′-tetrachloroazoxybenzene in soybean plants grown in treated soils . Chemosphere , 13 : 1103 – 1111 .
   Web of Science ®Google Scholar
• Brown , A. , Olivero , J. , Holdan , W. and Ganey , P. 1998 . Neutrophil activation by polychlorinated biphenyls: structure-activity relationships . Toxicol. Sci. , 46 : 308 – 316 .
   PubMed Web of Science ®Google Scholar
• Falandysz , J. 2003 . Chloronaphthalenes as food-chain contaminants: A review . Food Addit. Contam. , 20 : 995 – 1014 .
   PubMed Web of Science ®Google Scholar
• Nose , K. , Falandysz , J. , Wyrzykowska , B. , Orlikowska , A. and Noma , Y. 2009 . By-side PCDD/Fs in technical PCB formulations of Kanechlor series . J. Environ. Sci. Health Part A , 44 : 1528 – 1537 .
   Web of Science ®Google Scholar
• Vilavert , L. , Nadal , M. , Mari , M. , Schuhmacher , M. and Domingo , J. L. 2009 . Modification of an environmental survillance program to monitor PCDD/Fs and metals around a municipal solid waste incinerator . J. Environ. Sci. Health Part A , 44 ( 13 ) : 1343 – 1352 .
   Web of Science ®Google Scholar
• Puzyn , J. and Falandysz , J. 2005 . Octanol/water partition coefficients of chloronaphthalenes . J. Environ. Sci. Health Part A , 40 ( 14 ) : 1651 – 1663 .
   Web of Science ®Google Scholar
• Puzyn , T. and Falandysz , J. 2005 . Computational estimation of logarithm of n-octanol/air partition coefficient and subcooled vapour pressures of 75 chloronaphthalene congeners . Atmos. Environ. , 39 : 1439 – 1446 .
   Web of Science ®Google Scholar
• Puzyn , T. , Rostkowski , P. , Świeczkowski , A. , Jędrusiak , A. and Falandysz , J. 2006 . Prediction of environmental partition coefficients and the Henry's law constans for 135 congeners of chlorodibenzothiophene . Chemosphere , 62 : 1817 – 1828 .
   PubMed Web of Science ®Google Scholar
• Rayne , S. and Forest , K. 2009 . 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 Part A , 44 ( 13 ) : 1374 – 1387 .
   Web of Science ®Google Scholar
• Rayne , S. and Forest , K. 2010 . pKa values of the monohydroxylated polychlorinated biphenyls (OH-PCBs), polybrominated biphenyls (OH-PBBs), polychlorinated diphenyl ethers (OH-PCDEs), and polybrominated diphenyl ethers (OH-PBDEs) . J. Environ. Sci. Health Part A , 45 ( 11 ) : 1322 – 1346 .
   Web of Science ®Google Scholar
• Falandysz , J. , Puzyn , T. , Szymanowska , B. , Kawano , M. , Markuszewski , M. , Kaliszan , R. , Skurski , O. , Błażejowski , J. and Wakimoto , T. 2001 . 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. , 10 ( 4 ) : 217 – 235 .
   Web of Science ®Google Scholar
• Puzyn , T. and Falandysz , J. 2007 . 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 , 36 ( 1 ) : 203 – 214 .
   Web of Science ®Google Scholar
• Puzyn , T. , Falandysz , J. , Jones , P. D. and Giesy , J. P. 2007 . Quantitative structure-activity relationships for the prediction of relative in vitro potencies (REPs) for chloronaphthalenes . J. Environ. Sci. Health Pt. A , 42 ( 5 ) : 573 – 590 .
   Web of Science ®Google Scholar
• Rayne , S. and Forest , K. 2009 . 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 Part A , 44 ( 13 ) : 1388 – 1399 .
   Web of Science ®Google Scholar
• Rayne , S. and Forest , K. 2010 . 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 Part A , 45 ( 3 ) : 355 – 362 .
   Web of Science ®Google Scholar
• Rayne , S. and Forest , K. 2010 . Modeling the hydrolysis of perfluorinated compounds containing carboxylic and phosphoric acid ester functions and sulfonamide groups . J. Environ. Sci. Health Part A , 45 ( 4 ) : 432 – 446 .
   Web of Science ®Google Scholar
• Rayne , S. and Forest , K. 2010 . 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 Part A , 45 ( 12 ) : 1550 – 1594 .
   Web of Science ®Google Scholar
• Wilczyńska-Piliszek , A. , Piliszek , S. and Falandysz , J. 2012 . 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 trans-azobenzene congeners . J. Environ. Sci. Health Part B , 47 accepted
   PubMedGoogle Scholar
• Pliszek , S. , Wilczyńska-Piliszek , A. and Falandysz , J. 2011 . N-octanol-water partition coefficients (log KOW) of 399 congeners of polychlorinated azoxybenzenes (PCAOBs) determined by QSPR and ANN based approach . J. Environ. Sci. Health Part A , 46 ( 14 ) : 1748 – 1762 .
   Google Scholar
• Pliszek , S. , Wilczyńska-Piliszek , A. and Falandysz , J. 2012 . The aqueous solubility of some herbicidal by-side toxic impurities: Predicted data of the 399 chlorinated trans-azoxybenzene congeners . J. Environ. Sci. Health Part B , 47 accepted
   Google Scholar
• Wilczyńska-Piliszek , A. , Pliszek , S. and Falandysz , J. 2012 . QSAR and ANN for the estimation of water solubility of 209 polychlorinated trans-azobenzenes . J. Environ. Sci. Health Part A , 47 accepted
   Google Scholar
• Wilczyńska-Piliszek , A. , Pliszek , S. and Falandysz , J. 2012 . QSPR models for prediction of the soil sorption coefficient (log KOC) values of 209 polychlorinated trans-azobenzenes (PCt-ABs) . J. Environ. Sci. Health Part A , 47 accepted
   Google Scholar
• StatSoft . 2006 . Elektroniczny podręcznik statystyki PL , Kraków . http://www.statsoft.pl/textbook/stathome.html
   Google Scholar
• Statistica neural network PL . 2001 . Kurs użytkowania programu na przykładach , Kraków : StatSoft Polska Sp. z o.o. .
   Google Scholar
• http://www.cmbi.ru.nl/molden/
   Google Scholar
• http://www.brothersoft.com/acd-chemsketch-133131.html
   Google Scholar
• http://www.gaussian.com/g_tech/g_ur/m_basis_sets.htm
   Google Scholar
• McLean , A. D. and Chandler , G. S. 1980 . Contracted Gaussian-basis sets for molecular calculations. 1. 2nd row atoms, Z = 11-18 . J. Chem. Phys. , 72 : 5639 – 5648 .
   Web of Science ®Google Scholar
• Raghavachari , K. , Binkley , J. S. , Seeger , R. and Pople , J. A. 1980 . Self-consistent molecular orbital methods. 20. Basis set for correlated wave-functions . J. Chem. Phys. , 72 : 650 – 654 .
   Web of Science ®Google Scholar
• Blaudeau , J.-P. , McGrath , M. P. , Curtiss , L. A. and Radom , L. 1997 . Extension of Gaussian-2 (G2) theory to molecules containing third-row atoms K and Ca . J. Chem. Phys. , 107 : 5016 – 5021 .
   Web of Science ®Google Scholar
• Wachters , J. H. 1970 . Gaussian basis set for molecular wave functions containing third-row atoms . J. Chem. Phys. , 52 : 1033
   Web of Science ®Google Scholar
• Hay , P. J. 1977 . Gaussian basis sets for molecular calculations—Representation of 3D orbitals in transition-metal atoms . J. Chem. Phys.6 , 66 : 4377 – 4384 .
   Web of Science ®Google Scholar
• Raghavachari , K. and Trucks , G. W. 1989 . Highly correlated systems: Excitation energies of first row transition metals Sc-Cu . J. Chem. Phys. , 91 : 1062 – 1065 .
   Web of Science ®Google Scholar
• Binning , R. C. Jr. and Curtiss , L. A. 1990 . Compact contracted basis-sets for 3rd-row atoms - GA-KR . J. Comp. Chem. , 11 : 1206 – 1216 .
   Web of Science ®Google Scholar
• McGrath , M. P. and Radom , L. 1991 . Extension of Gaussian-1 (G1) theory to bromine-containing molecules . J. Chem. Phys. , 94 : 511 – 516 .
   Web of Science ®Google Scholar
• Curtiss , L. A. , McGrath , M. P. , Blaudeau , J.-P. , Davis , N. E. , Binning , R. C. Jr. and Radom , L. 1995 . Extension of Gaussian-2 theory to molecules containing third-row atoms Ga-Kr . J. Chem. Phys. , 103 : 6104 – 6113 .
   Web of Science ®Google Scholar
• Frisch , M. J. , Trucks , G. W. , Schlegel , H. B. , Scuseria , G. E. , Robb , M. A. , Cheeseman , J. R. , Montgomery , J. A. , Vreven , T. Jr. , 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. and Pople , J. A. 2003 . Pittsburgh , PA : Gaussian, Inc. .
   Google Scholar
• MOPAC . 2006 . Version 1.0, J.J.P , Tokyo , , Japan : Stewart, Fujitsu Limited .
   Google Scholar
• Rocha , G. B. , Freire , R. O. , Sima , A. M. and Stewart , J. J.P. 2006 . RM1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I . J. Comp. Chem. , 27 ( 10 ) : 1101 – 1111 .
   PubMed Web of Science ®Google Scholar
• http://www.rm1.sparkle.pro.br/rm1-software/mopac2009
   Google Scholar
• Stewart , J. J.P. 2007 . Optimization of parameters for semiempirical methods V: Modification of NDDO approximations and application to 70 elements . J. Mol. Mod. , 13 : 1173 – 1213 .
   PubMed Web of Science ®Google Scholar
• Burstein , K. Y. and Isaew , A. N. 1984 . MNDO calculations on hydrogen bonds. Modified function for core-core repulsion . Theor. Chim. Acta , 64 : 397 – 401 .
   Google Scholar
• Jaworski , B. M. and Dietlaf , A. A. 1995 . Fizyka poradnik encyklopedyczny , Warszawa : Wydawnictwo Naukowe PWN .
   Google Scholar
• Morrisom , R. T. and Boyd , R. N. 1998 . Chemia organiczna, tom 1 , Warszawa : Państwowe Wydawnictwo Naukowe .
   Google Scholar
• Ochterski , J. W. Thermochemistry in Gaussian . 2000 www.gaussian.com
   Google Scholar
• Pigoń , K. and Ruziewicz , Z. 1980 . Chemia fizyczna , Warszawa : Państwowe Wydawnictwo Naukowe .
   Google Scholar
• Rice , S. A. 2005 . Advances in Chemical Physics , New York : Wiley-IEEE .
   Google Scholar
• Stasicka , Z. and Achmatowicz , O. 2005 . Kompendium terminologii chemicznej , ZamKor .
   Google Scholar
• Todeschini , R. and Consonni , V. 2000 . Handbook of Molecular Descriptors, vol, 11 , Weinheim : Wiley-VCH .
   Google Scholar
• Tomasi , J. and Persico , M. 1994 . Molecular interactions in solution: An overview of methods based on continuous distributions of the solvent . Chem. Rev. , 94 : 2027 – 2094 .
   Web of Science ®Google Scholar
• Yang , W. and Parr , R. G. 1985 . Hardness, softness, and the fuki function in the electronic theory of metals and catalysis . Proc. Nat. Acad. Sci. USA , 82 : 6723 – 6726 .
   PubMed Web of Science ®Google Scholar
• Zhan , C.-G. , Nichols , J. A. and Dixon , D. A. 2003 . Ionization potential, electron affinity, electronegativity, hardness, and electron exciation energy: Molecular properties from density functional theory orbital energies . J. Phys. Chem. A , 107 ( 20 ) : 4184 – 4195 .
   Web of Science ®Google Scholar
• Alparone , A. , Librando , V. and Minniti , Z. 2008 . Validation of semiempirical PM6 method for the prediction of molecular properties of polycyclic aromatic hydrocarbons and fullerenes . Chem. Phys. Lett. , 460 : 151 – 154 .
   Web of Science ®Google Scholar
• Alparone , A. and Librando , V. 2009 . Electronic dipole polarizabilities of polychlorinated dibenzofurans and semiempirical PM6 level performance . J. Mol. Str. Theochem. , 894 : 128
   Web of Science ®Google Scholar
• Wania , F. and Mackay , D. 1996 . Tracking the distribution of persistent organic pollutants . Environ. Sci. Technol. , 30 : 390A – 396A .
   PubMed Web of Science ®Google Scholar