Studies of thermodynamic properties and relative stability of a series of polyfluorinated dibenzo-p-dioxins by density functional theory

Journal of Hazardous Materials

Volumn 181, Issue 1-3, 2010, Pages 969-974

  Yang, Xi ^a   Liu, Hui ^b   Hou, Haifeng ^c   Flamm, Alison ^a   Zhang, Xuesheng ^c   Wang, Zunyao ^a  

^a NANJING UNIVERSITY   (China)

^b JIAXING UNIVERSITY   (China)

^c CHANGZHOU UNIVERSITY   (China)

Author keywords

Number and position of fluorine atom substitution (NPFS); Polyfluorinated dibenzo p dioxins; Relative stability; Thermodynamic property

Indexed keywords

DIBENZO-P-DIOXINS; FLUORINE ATOMS; GAUSSIANS; IDEAL GAS; ISODESMIC REACTIONS; RELATIVE STABILITIES; RELATIVE STABILITY; STANDARD ENTHALPY OF FORMATION; THERMODYNAMIC PARAMETER;

DENSITY FUNCTIONAL THEORY; FLUORINE; ORGANIC POLLUTANTS; STABILITY; THERMODYNAMIC PROPERTIES;

ATOMS;

DIBENZODIOXIN DERIVATIVE; FLUORINE; POLYFLUORINATED DIBENZO 4 DIOXIN; UNCLASSIFIED DRUG; DIBENZO(1,4)DIOXIN; DIOXIN;

DIOXIN; ENTHALPY; ENTROPY; ORGANOFLUORINE; THERMODYNAMICS;

ARTICLE; ATOM; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENTHALPY; ENTROPY; GAS; KERNEL METHOD; MAGNITUDE ESTIMATION METHOD; MOLECULAR STABILITY; SUBSTITUTION REACTION; THERMODYNAMICS; CHEMISTRY; HALOGENATION;

DIOXINS; HALOGENATION; MODELS, MOLECULAR; THERMODYNAMICS;

EID: 77954542310     PISSN: 03043894     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2010.05.108     Document Type: Article

References (25)

1. Weber R., Schrenk D., Schmitz H.J., Hagenmaier A., Hagenmaier H. Polyfluorinated dibenzodioxins and dibenzofurans-synthesis, analysis, formation and toxicology. Chemosphere 1995, 30:629-639.
2. Sakai S., Hiraoka M., Shiozaki K. Thermal behavior of chlorofluorocarbons (CFCs) a formation of PCDDs/PCDFs & PFDDs/PFDFs. Organohalogen Compd. 1995, 23:347-351.
3. Haffer U., Rotard W., Mailahn W., Schuize G. Synthesis of polyfluorinated dibenzo-p-dioxins. Organohalogen Compd. 1993, 11:87-90.
4. Haffer U., Rotard W., Mailahn W. Synthesis of polyfluorinated dibenzo-p-dioxins. Chemosphere 1994, 29:1803-1809.
5. Haffer U., Rotard W., Pickardt J. Synthesis and X-ray crystal structure of 1,2,4,6,7,9-hexafluorodibenzo-p dioxin. J. Fluorine Chem. 1995, 73:265-266.
6. Haffer U., Conrad D., Rotard W. Contributions to the GC-MS-analysis of polyfluorinated dibenzo-p-dioxins. Fres. J. Anal. Chem. 1996, 354:359-361.
7. Conrad D., Golor G., Neubert D., Rotard W. Kinetic properties of three polyfluorinated dibenzo-p-dioxins in rats. Organohalogen Compd. 1996, 29:406-411.
8. Herzke D., Thiel R., Rotard W.D., Neubert D. Kinetics and organotropy of some polyfluorinated dibenzo-p-dioxins and dibenzofurans (PFDD/PFDF) in rats. Life Sci. 2002, 71:1475-1486.
9. Weber R., Schmib H.J., Schrend D., Hagenmaier H. Metabolic degradation, inducing potency, and metabolites of fluorinated and chlorinated-fluorinated dibenzodioxins and dibenzofurans. Chemosphere 1997, 34:29-40.
10. Weber R., Hagenmaier H. Synthesis and analysis of mixed chlorinated-fluorinated dibenzo-p-dioxins and dibenzofurans and assessment of formation and occurrence of the fluorinated and chlorinated-fluorinated dibenzo-p-dioxins and dibenzofurans. Chemosphere 1997, 34:13-28.
11. x (x=1-8). J. Hazard. Mater. 2009, 164:1552-1555.
12. x (x=1-8). J. Hazard. Mater. 2009, 164:1595-1600.
13. Wang Z.Y., Zhai Z.C., Wang L.S., Chen J.L., Kikuchi O., Watanabe T.J. Prediction of gas phase thermodynamic function of polychlorinated dibenzo-p-dioxins using DFT. J. Mol. Struct. (THEOCHEM) 2004, 672:97-104.
14. Wang Z.Y., Zhai Z.C., Wang L.S. Prediction of gas phase thermodynamic properties of polychlorinated dibenzo-furans by DFT. J. Mol. Struct. (THEOCHEM) 2005, 725:55-62.
15. Liu H., Sun P., Liu H.X., Wang Z.Y. Study of structural and thermodynamic properties for polychlorinated thianthrenes by density functional theory. Chin. J. Struct. Chem. 2008, 27:1255-1260.
16. Wei X.Y., Liu H., Wang Z.Y., Zhu J.J. Computational note on thermodynamic function of polychlorinated phenoxathiins (PCPTs). J. Mol. Struct. (THEOCHEM) 2008, 857:126-127.
17. Yu J., Zhang X.C., Wang Z.Y., Zeng X.L. Study on the thermodynamic properties and stability of series of polybrominated dibenzo-furans by density functional theory. Acta Chim. Sin. 2006, 64:1961-1968.
18. Wang H.D., Liu H., Li C.C., Wang Z.Y. DFT calculation on PBPXs: their gas phase thermodynamic function and implication of Br substituted position. Thermochim. Acta 2009, 487:49-53.
19. Wang C., Fang Z.Y., Abraham F.J., Xu S., Liu H. DFT study of structural and thermodynamic properties for polybrominated 5, 10-dihydrophenazines. Int. J. Thermophys. 2009, 30:1875-1890.
20. Wang C., Fang Z.Y., Liu H., Xu S. Thermodynamic properties and relative stability of polybrominated phenoxathiins by density functional theory. Int. J. Phys. Sci. 2008, 3:250-256.
21. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 03, Revision A.1, Gaussian, Inc., Pittsburgh, 2003.
22. Lee J.E., Choi W., Mhin B.J. DFT Calculation on the thermodynamic properties of polychlorinated dibenzo-p-dioxins: intramolecular Cl-Cl repulsion effects and their thermochemical implications. J. Phys. Chem. A. 2003, 107:2693-2699.
23. EI-Taher S. Ab initio and DFT investigation of fluorinated methyl hydroperoxides: structures, rotational barriers, and thermochemical properties. J. Fluorine Chem. 2009, 127:54-62.
24. x (x=1, 2). J. Fluorine Chem. 2002, 116:135-141.
25. Dean J.A. Lange's Handbook of Chemistry 1985, Science Press, McGraw-Hill Book Company. thirteenth ed.