147
Views
0
CrossRef citations to date
0
Altmetric
Original Articles

Theoretical studies on heats of formation of chlorinated and fluorinated benzene derivatives

, , &
Pages 1105-1112 | Received 08 Mar 2011, Accepted 10 Apr 2011, Published online: 12 Aug 2011

References

  • Golovin , A.V. , Ponomarev , D.A. and Takhistov , V.V. 2010 . Thermochemistry of organic, heteroorganic, and inorganic molecules and their fragments. Quantum-chemical calculations of thermochemical parameters: Molecules and their fragments . Theor. J. Comput. Chem. , 9 : 125 – 153 .
  • Beurskens , J.E.M. , Dekker , C.G.C. , van den Heuvel , H. , Swart , M. , de Wolf , J. and Dolfing , J. 1994 . Dechlorination of chlorinated benzenes by an anaerobic microbial consortium that selectively mediates the thermodynamic most favorable reactions . J. Environ. Sci. Technol. , 28 : 701 – 706 .
  • Karnofsky , B. 1996 . Hazardous Waste Management Compliance Handbook , 2nd ed. , New York : Van Nostrand Reinhold .
  • Safe , S. 1990 . Polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs), and related compounds: environmental and mechanistic considerations which support the development of toxic equivalency factors (TEFs) . Crit. Rev. Toxicol. , 21 : 51 – 88 .
  • Lee , J.E. , Choi , W. and Mhin , B.J. 2003 . DFT calculation on the thermodynamic properties of polychlorinated dibenzo-p-dioxins: Intramolecular Cl-Cl repulsion effects and their thermochemical implications . J. Phys. Chem. A , 107 : 2693 – 2699 .
  • Namazian , M. and Coote , M.L. 2009 . Gas-phase acidity, bond dissociation energy and enthalpy of formation of fluorine-substituted benzenes: A theoretical study . J. Fluor. Chem. , 130 : 621 – 628 .
  • Frisch , M.J. , Trucks , G.W. , Schlegel , H.B. , Scuseria , G.E. , Robb , M.A. , Cheeseman , J.R. , Montgomery , J.A. Jr , Vreven , 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. , Li , X. , Knox , J.E. , Hratchian , H.P. , Cross , J.B. , Bakken , V. , 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. 2004 . Gaussian 03, Revision C.02 , Wallingford CT : Gaussian, Inc. .
  • Hehre , W.J. , Radom , L. , Schleyer , P.v.R. and Pople , J.A. 1986 . Ab Initio Molecular Orbital Theory , New York : Wiley .
  • Berry , R.J. , Burgess , D.R.F. Jr. , Nyden , M.R. , Zachariah , M.R. and Schwartz , M. 1995 . Halon thermochemistry: Ab initio calculations of the enthalpies of formation of fluoromethanes . J. Phys. Chem. , 99 : 17145 – 17150 .
  • Gurvich , L.V. , Veyts , I.V. , Alcock , C.B. and Iorish , V.S. 1994 . Thermodynamic Properties of Individual Substances , 4th ed. , Boca Raton, FL : CRC Press .
  • Platonov , V.A. and Simulin , Y.N. 1983 . Standard enthalpies of formation of 1,2,3-trichlorobenzene, 1,2,4,5-tetrachlorobenzene, and hexachlorobenzene . Russ. J. Phys. Chem. , 57 : 840 – 842 .
  • Platonov , V.A. and Simulin , Y.N. 1984 . Experimental determination of the standard enthalpies of formation of polychlorobenzenes. II. Standard enthalpies of formation of dichlorobenzenes . Russ. J. Phys. Chem. , 58 : 1630 – 1632 .
  • Platonov , V.A. and Simulin , Y.N. 1985 . Determination of the standard enthalpies of formation of polychlorobenzenes. III. The standard enthalpies of formation of mono-1,2,4- and 1,3,5-tri-, and 1,2,3,4- and 1,2,3,5-tetrachlorobenzenes . Russ. J. Phys. Chem. , 59 : 179 – 181 .
  • Platonov , V.A. , Simulin , Y.N. and Rozenberg , M.M. 1985 . Standard heat of formation of pentachlorobenzene. Calculation of ΔHc°(g) and ΔEs°(g) of polychlorobenzenes by the Tatevskii method . Russ. J. Phys. Chem. , 59 : 814 – 817 .
  • Yan , H. , Gu , J. , An , X. and Hu , R. 1987 . Standard enthalpies of formation and isomerization of trichlorobenzenes . Huaxue Xuebao , 45 : 1184 – 1187 .
  • Stull , D.R. , Westrum , E.F. and Sinke , G.C. 1969 . The Chemical Thermodynamics of Organic Compounds , New York : Wiley .
  • Cox , J.D. and Pilcher , G. 1970 . Thermochemistry of Organic and Organometallic Compounds , New York : Academic Press .
  • Pedley , J.B. 1994 . Thermochemical Data and Structures of Organic Compounds , 2nd ed. , College Station, TX : Thermodynamics Research Center .
  • Pedley , J.B. , Naylor , R.D. and Kirby , S.P. 1986 . Thermodynamic Data of Organic Compounds , 2nd ed. , London : Chapman and Hall .
  • Sabbah , R. and An , X.W. 1991 . Thermodynamic Analysis of Chlorobenzenes . Thermochim. Acta , 179 : 81 – 88 .
  • Good , W.D. , Lacina , J.L. , Scott , D.W. and McCullough , J.P. 1962 . Combustion calorimetry of organic fluorine compounds. The heats of combustion and formation of the difluorobenzenes, 4-fluorotoluene and m-trifluorotoluic acid . J. Phys. Chem. , 66 : 1529 – 1532 .
  • Harrop , D. and Head , A.J. 1978 . Thermodynamic properties of fluorine compounds. 18. Enthalpy of combustion of 1,2,4,5-tetrafluorobenzene . J. Chem. Thermodyn. , 10 : 705 – 706 .
  • Cox , J.D. , Gundry , H.A. , Harrop , D. and Head , A.J. 1969 . Thermodynamic properties of fluorine compounds. 9. Enthalpies of formation of some compounds containing the pentafluorophenyl group . J. Chem. Thermodyn. , 1 : 77 – 87 .
  • Stewart , J.J.P. 2004 . Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation . J. Mol. Model. , 10 : 6 – 10 .
  • Handzlik , J. and Sautet , P. 2008 . Structure of isolated molybdenum (VI) oxide species on gamma-Alumina: A periodic density functional theory study . J. Phys. Chem. C , 112 : 14456 – 14463 .
  • Büker , H.H. , Nibbering , N.M.M. , Espinosa , D. , Mongin , F. and Schlosser , M. 1997 . Additivity of substituent effects in the fluoroarene series: Equilibrium acidity in the gas phase and deprotonation rates in ethereal solution . Tetrahedron Lett. , 38 : 8519 – 8522 .
  • Wang , L. , Heard , D.E. , Pilling , M.J. and Seakins , P. 2008 . A gaussian-3X prediction on the enthalpies of formation of chlorinated phenols and dibenzo-p-dioxins . J. Phys. Chem. A , 112 : 1832 – 1840 .
  • Gomes , J.R.B. and Ribeiro da Silva , M.A.V. 2006 . Gas-phase enthalpies of formation of the fluorobenzenes family and their dewar isomers from ab initio calculations . J. Mol. Struct. (Theochem) , 778 : 77 – 84 .
  • Su , M.D. and Chu , S.Y. 1999 . Density functional study of some germylene insection reactions . J. Am. Chem. Soc. , 121 : 4229 – 4237 .
  • NIST Chemistry Web Book: NIST Standard Reference Database, Number 69, June 2005 Release. Available at: http://webbook.nist.gov/chemistry/

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.