QSAR and ANN for the estimation of water solubility of 209 polychlorinated trans-azobenzenes

References

• 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
• McMillan , D. C. , Bradshaw , T. P. , Hinson , J. A. and Jollow , D. J. 1991 . Role of metabolites in propanil-induced hemolytic anemia . Toxicol. Appl. Pharmacol. , 110 : 70 – 78 .
   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
• 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
• 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 ( 7 ) : 1131 – 1142 .
   PubMed Web of Science ®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
• 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
• Piliszek , S. , Wilczyńska-Piliszek , A. J. , Puzyn , T. 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 .
   Web of Science ®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 doi 10.1080/03601234.2012.638885
   Google Scholar
• Bartha , R. , Linke , H. A.B. and Pramer , D. 1968 . Pesticide transformations: Production of chloroazobenzenes from chloroanilines . Science , 161 : 582 – 583 .
   PubMed Web of Science ®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
• Lee , J. K. and Fournier , J. C. 1978 . A study on the evolution of 3,4-DCA and TCAB in some selected soil: II Degradation of 14C-3,4-DCA and 14C –TCAB . J. Korean Agr. Chem. Soc. , 21 : 71 – 80 .
   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
• Zhao , W. , Wu , Ch. and Iwamoto , M. 1999 . Rate-equation theory of azobenzene monolayer photoisomeration . Chem. Phys. Lett. , 312 : 572 – 577 .
   Web of Science ®Google Scholar
• Hashimoto , S. , Schneider , S. , Yamamoto , T. and Morita , M. 1994 . Aqueous solubility and octanol-water partition coefficient of 3,3’,4,4’-tetrachloroazobenzene . Organohalogen Cmpds , 20 : 125 – 128 .
   Web of Science ®Google Scholar
• Hsia , M. T.S. , Bairstow , F. V.Z. , Shih , L. C.T. , Pounds , J. G. and Allen , J. R. 1977 . 3,4,3’,4’-tetrachloroazobenzene: A potential environmental toxicant . Res. Comm. Chem. Pathol. Pharmacol. , 17 : 225 – 236 .
   PubMedGoogle Scholar
• United States Environmental Protection Agency (USEPA) . 1985 . Health and Environmental Effects Profile for TCAB, TCAOB and TCHB , Cincinati , OH : Environmental Criteria and Assessment Office, Office of Health and Environmental Assessment, Office of Research and Development, U.S. Environmental Protection Agency . EPA/600/X-85/394
   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, Florida , , USA : CRC Press .
   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 doi 10.1080/03601234.2012.616779
   PubMedGoogle 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
• 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 Pt. A , 44 ( 13 ) : 1388 – 1399 .
   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 Pt. A , 44 ( 13 ) : 1374 – 1387 .
   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 . 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
• 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
• 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 . 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 and Falandysz , J . 2005 . Octanol/water partition coefficients of chloronaphthalenes . J. Environ. Sci. Health, Part A , 40 : 1651 – 1663 .
   Web of Science ®Google Scholar
• Mackay , D. , Shiu , W. Y. and Ma , K. Ch . 1992 . Illustratrated handbook of physical-chemical properties and environmental fate for organic chemicals, volume II, polynuclear aromatic hydrocarbons, polychlorinated dioxins, and dibenzofurans , Chelsea , MI : Lewis Publishers .
   Google Scholar
• Wang , Y. H. and Wong , P. K. 2002 . Mathematical relationships between vapor pressure, water solubility, Henry's law constant, n-octanol/water partition coefficient and gas chromatographic retention index of polychlorinated dibenzo-p-dioxins . Water Res. , 36 : 350 – 355 .
   PubMed Web of Science ®Google Scholar
• Puzyn , T. and Falandysz , J. 2007 . Application and comparison of different chemometric approaches in QSPR modeling of supercooled liquid vapour pressure for chloronaphthalenes . SAR and QSAR Environ. Res. , 18 : 299 – 313 .
   PubMed 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. , 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
• 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/k_dft.htm; 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 wavefunctions 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. , 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 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. Gaussian, Inc. Pittsburgh , PA 2003
   Google Scholar
• Piela , L. 2003 . Idee chemii kwantowej , Warszawa : Wydawnictwo Naukowe PWN .
   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
• Stewart , J. J.P. “MOPAC” , Colorado Springs , , CO; USA : Stewart Computational Chemistry . http://OpenMOPAC.net
   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
• 2009 . http://www.rm1.sparkle.pro.br/rm1-software/mopac
   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
• Bielański , A. 1999 . Podstawy chemii nieorganicznej, część 1 , Warszawa : Wyd. Nauk. PWN .
   Google Scholar
• Burstein , K. Y. and Isaew , A. N. 1984 . MNDO calculations on hydrogen bonds. Modified function for core-core repulsion . Theoret. 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. 1988 . Chemia organiczna, tom 1 , Warszawa : Państwowe Wydawnictwo Naukowe .
   Google Scholar
• Ochterski , J. W. 2000 . Thermochemistry in Gaussian . www.gaussian.com
   Google Scholar
• Pigoń , K. and Ruziewicz , Z. 1980 . Chemia fizyczna , Warszawa : Państwowe Wydawnictwo Naukowe .
   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
• Rice , S. A. 2005 . Advances in chemical physics , New York : Wiley-IEEE .
   Google Scholar
• Stasicka , Z. and Achmatowicz , O. 2005 . Kompendium terminologii chemicznej . Zamkom ,
   Google Scholar
• Wyrzykowska , B. , Szymczyk , K. , Ichihashi , H. , Falandysz , J. and Yamasaki , S. 2001 . Application of HR/ICP/MS and principal component analysis for studying interdependences among 23 trace elements in Polish beers . J. Agric. Food Chem. , 49 ( 7 ) : 3425 – 3431 .
   PubMed Web of Science ®Google Scholar
• 2006 . StatSoft. Elektroniczny podręcznik statystyki PL. Krakówhttp://www.statsoft.pl/textbook/stathome.html
   Google Scholar
• 2001 . Statistica neural network PL, Kurs użytkowania programu na przykładach , Kraków : StatSoft Polska Sp. z o.o. .
   Google Scholar
• Puzyn , T. , Mostrąg , A. , Falandysz , J. , Kholod , J. and Leszczyński , J. 2009 . Predicting water solubility of congeners: Chloronaphthalenes—A case study . J. Hazard. Mat. , 170 : 1014 – 1022 .
   PubMed 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