Single-descriptor based quantum-chemical QSPRs for physico-chemical properties of polychlorinated-dibenzo-p-dioxins and -dibenzo-furans (PCDD/Fs): Exploring the role of electron-correlation

Chemosphere

Volumn 118, Issue 1, 2015, Pages 239-245

  Vikas, ^a   Chayawan, ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

PCDDs; PCDFs; Persistent organic pollutants; QSPR; Quantum chemical descriptors

Indexed keywords

ALCOHOLS; AROMATIC COMPOUNDS; CHEMICAL ANALYSIS; CHEMICAL BONDS; ELECTRON CORRELATIONS; ELECTRONEGATIVITY; QUANTUM CHEMISTRY;

PCDDS; PCDFS; PERSISTENT ORGANIC POLLUTANT (POP); QSPR; QUANTUM CHEMICAL DESCRIPTORS;

ORGANIC POLLUTANTS;

DIBENZODIOXIN DERIVATIVE; DIBENZOFURAN DERIVATIVE; OCTANOL; WATER; 2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; BENZOFURAN DERIVATIVE; CHLORINATED DIBENZOFURANS; POLLUTANT; POLYCHLORODIBENZO-4-DIOXIN;

CORRELATION; ELECTRON; INDEX METHOD; NUMERICAL MODEL; ORGANIC POLLUTANT; PCDD; PCDF; PHYSICOCHEMICAL PROPERTY; PREDICTION; QUANTUM MECHANICS; SOLUBILIZATION;

AIR; AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; CORRELATION ANALYSIS; CORRELATION COEFFICIENT; DENSITY FUNCTIONAL THEORY; DIPOLE; ELECTRON; ELECTRON CORRELATION; ELECTROPHILICITY; ENERGY; EXTERNAL VALIDITY; INTERNAL VALIDITY; PARTITION COEFFICIENT; PERSISTENT ORGANIC POLLUTANT; PHYSICAL CHEMISTRY; POLARIZATION; PREDICTION; QUANTITATIVE STRUCTURE PROPERTY RELATION; QUANTUM CHEMISTRY; SOLUBILITY; VAPOR PRESSURE; ANALOGS AND DERIVATIVES; CHEMICAL MODEL; CHEMISTRY; POLLUTANT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM THEORY;

1-OCTANOL; BENZOFURANS; ELECTRONS; ENVIRONMENTAL POLLUTANTS; MODELS, CHEMICAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY; SOLUBILITY; TETRACHLORODIBENZODIOXIN; VAPOR PRESSURE; WATER;

EID: 84922326308     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2014.08.072     Document Type: Article

References (34)

1. Becke A.D. Density-functional thermochemistry III. The role of exact exchange. J. Chem. Phys. 1993, 98:5648-5652.
2. Chirico N., Gramatica P. Real external predictivity of QSAR models: how to evaluate it? Comparison of different validation criteria and proposal of using the concordance correlation coefficient. J. Chem. Inf. Model. 2011, 51:2320-2335.
3. Chirico N., Gramatica P. Real external predictivity of QSAR models. Part 2. New intercomparable thresholds for different validation criteria and the need for scatter plot inspection. J. Chem. Inf. Model. 2012, 52:2044-2058.
4. Chirico, N., Papa, E., Kovarich, S., Cassani, S., Gramatica, P., 2012. QSARINS, Software for QSAR MLR Model Development and Validation, QSAR Res. Unit in Environ. Chem. and Ecotox. DiSTA, University of Insubria, Varese, Italy. http://www.qsar.it.
5. 2 parameter for QSAR validation. J. Chem. Inf. Model. 2009, 49:1669-1678.
6. Frisch, M.J., et al., 2004. Gaussian 03, Revision D.01, Gaussian Inc., Wallingford, CT.
7. Gramatica P., Chirico N., Papa E., Cassani S., Kovarich S. QSARINS: a new software for the development, analysis and validation of QSAR MLR model, software news and updates. J. Comput. Chem. 2013, 34:2121-2132.
8. Harner T., Green N.J.L., Jones K.C. Measurements of octanol-air partition coefficients for PCDD/Fs: a tool in assessing air-soil equilibrium status. Environ. Sci. Technol. 2000, 34:3109-3114.
9. Jensen F. Introduction to Computational Chemistry 2007, John Wiley & Sons, Chichester. second ed.
10. Löwdin P-.O. The historical development of the electron correlation problem. Int. J. Quant. Chem. 1995, 55:77-102.
11. Mackay D., Shiu W.Y., Ma K.C. Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals. Polynuclear Aromatic Hydrocarbons, Polychlorinated Dioxins, and Dibenzofurans 1992, vol. 2. Lewis Publishers, Boca Raton, FL.
12. Ojha P.K., Mitra I., Das R.N., Roy K. Further exploring rm2 metrics for validation of QSPR models dataset. Chemom. Intell. Lab. Syst. 2011, 107:194-205.
13. Parr R.G., Szentpály L., Liu S. Electrophilicity index. J. Am. Chem. Soc. 1999, 121:1922-1924.
14. Pearson R.G. Absolute electronegativity and hardness correlated with molecular orbital theory. Proc. Natl. Acad. Sic. USA 1986, 83:8440-8441.
15. Puzyn T., Suzuki N., Haranczyk M., Rak J. Calculation of quantum-mechanical descriptors for QSPR at the DFT level: Is it necessary?. J. Chem. Inf. Model. 2008, 48:1174-1180.
16. Reenu, Vikas Electron-correlation based externally predictive QSARs for mutagenicity of nitrated-PAHs in Salmonella typhimurium TA100. Ecotoxicol. Environ. Saf. 2014, 101:42-50.
17. Rocha G.B., Freire R.O., Simas A.M., Stewart J.J.P. RM1: a reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I. J. Comput. Chem. 2006, 27:1101-1111.
18. Rordorf B.F., Sarna L.P., Webster G.R.B. Vapor pressure determination for several polychlorodioxins by gas saturation method. Chemosphere 1986, 15:2073-2076.
19. Ruelle P. The n-octanol and n-hexane/water partition coefficient of environmentally relevant chemicals predicted from the mobile order and disorder (MOD) thermodynamics. Chemosphere 2000, 40:457-512.
20. Ruelle P., Kesselring U.W. Aqueous solubility prediction of environmentally important chemicals from the mobile order thermodynamics. Chemosphere 1997, 34:275-298.
21. Schüürmann G., Ebert R., Chen J., Wang B., Kühne R. External validation and prediction employing the predictive squared correlation coefficients test set activity mean vs training set activity mean. J. Chem. Inf. Model. 2008, 48:2140-2145.
22. Shi L.M., Fang H., Tong W., Wu J., Perkins R., Blair R.M., Branham W.S., Dial S.L., Moland C.L., Sheehan D.M. QSAR models using a large diverse set of estrogens. J. Chem. Inf. Comput. Sci. 2001, 41:186-195.
23. Shlu W.Y., Doucette W., Gobas F.A.P.C., Andren A., Mackay D. Physical-chemical properties of chlorinated dibenzo-p-dioxins. Environ. Sci. Technol. 1988, 22:651-658.
24. Stewart J.J.P. Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements. J. Mol. Model. 2007, 13:1173-1213.
25. Stewart, J.J.P., 2012. Stewart Computational Chemistry, MOPAC2012, Version 12.239W. http://OpenMOPAC.net.
26. Stewart J.J.P. Optimization of parameters for semiempirical methods VI: more modifications to the NDDO approximations and re-optimization of parameters. J. Mol. Model. 2013, 19:1-32.
27. Tropsha A., Gramatica P., Gombar V.K. The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb. Sci. 2003, 22:69-77.
28. Vikas, Reenu, Chayawan Does electron-correlation has any role in the quantitative structure-activity relationships?. J. Mol. Graph. Model. 2013, 42:7-16.
29. Vikas, Chayawan Externally predictive quantitative modeling of supercooled liquid vapour pressure of polychlorinated-naphthalenes through electron-correlation based quantum-mechanical descriptors. Chemosphere 2014, 95:448-454.
30. Xiao H., Wania F. Is vapor pressure or the octanol-air partition coefficient a better descriptor of the partitioning between gas phase and organic matter?. Atmos. Environ. 2003, 37:2867-2878.
31. w) of all polychlorinated dibenzo-furans (PCDF) and polychlorinated dibenzo-p-dioxins (PCDD) congeners by density functional theory. J. Mol. Struct.: Theochem. 2006, 766:25-33.
32. ow) of polychlorinated dibenzo-p-dioxins (PCDDs). QSAR Comb. Sci. 2007, 26:352-357.
33. Zeng X.-L., Wang H.-J., Wang Y. QSPR models of n-octanol/water partition coefficients and aqueous solubility of halogenated methyl-phenyl ethers by DFT method. Chemosphere 2012, 86:619-625.
34. Zeng X.-L., Zhang X.-L., Wang Y. QSPR modeling of n-octanol/air partition coefficients and liquid vapour pressures of polychlorinated dibenzo-p-dioxins. Chemosphere 2013, 91:229-232.