Thermochemical Similarities Among Three Reaction Systems: Vinyl + O₂ – Phenyl + O₂ – Dibenzofuranyl + O₂

REFERENCES

• Andino , J.M. , Smith , J.N. , Flagan , R.C. , Goddard , W.A. , and Seinfield , J.H. ( 1996 ) Mechanism of atmospheric photooxidation of aromatics: A theoretical study . J. Phys. Chem. , 100 , 10967 – 10980 .
   Web of Science ®Google Scholar
• Baboul , A.G. , Curtiss , L.A. , Redfern , P.C. , and Raghavachari , K. ( 1999 ) Gaussian-3 theory using density functional geometries and zero-point energies . J. Chem. Phys. A , 110 ( 16 ), 7650 – 7657 .
   Web of Science ®Google Scholar
• Becke , A.D. (1993) Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. , 98, 5648–5652.
   Web of Science ®Google Scholar
• Carpenter , B.K. ( 1993 ) Computational prediction of new mechanisms for the reactions of vinyl and phenyl radicals with molecular oxygen . J. Am. Chem. Soc. , 115 , 9806 – 9807 .
   Google Scholar
• Carpenter , B.K. ( 1995 ) Ab Initio computation of combustion kinetics. 1. Vinyl radical + O2 . J. Phys. Chem. , 99 , 9801 – 9810 .
   Google Scholar
• Chase , M.W. , Jr. ( 1998 ) NIST-JANAF Themochemical Tables, Fourth Edition, J. Phys. Chem. Ref. Data , Monograph 9 , 1 – 1951 .
   Google Scholar
• Chirico , R.D. , Gammon , B.E , Knipmeyer , S.E. , Nguyen , A. , Strube , M.M. , Tsonopoulos , C. , and Steele , W.V. ( 1990 ) The thermodynamic properties of dibenzofuran . J. Chem. Thermodynamics , 22 , 1075 – 1096 .
   Google Scholar
• Curtiss , L.A. , Raghavachari , K. , Redfern , P.C. , Rassolov , V. , and Pople , J. A. ( 1998 ) Gaussian-3 (G3) theory for molecules containing first and second-row atoms . J. Chem. Phys. A , 109 , 7764 – 7776 .
   Web of Science ®Google Scholar
• Cox , J.D. ( 1961 ) The heats of combustion of phenol and the three cresols . Pure Appl. Chem. , 2 , 125 – 128 .
   Google Scholar
• Cox , J.D. , Wagman , D.D. , and Medvedev , V.A. ( 1984 ) CODATA Key Values for Thermodynamics , Hemisphere Publishing Corp. , New York , p. 1 .
   Google Scholar
• Curtiss , L.A. , Raghavachari , K. , Redfern , P.C. , and Pople , J.A. ( 2000 ) Assessment of Gaussion-3 and density functional theories for a larger experimental test set . J. Chem. Phys. , 112 , 7374 – 7383 .
   Web of Science ®Google Scholar
• Durant , J.L. ( 1996 ) Evaluation of transition state properties by density functional theory . Chem. Phys. Lett. , 256 , 595 – 602 .
   Web of Science ®Google Scholar
• da Silva , G. , Kim , C.-H. , and Bozzelli , J.W. ( 2006 ) Thermodynamic properties (Enthalpy, bond energy, entropy, and heat capacity) and internal rotor potentials of vinyl alcohol, methyl vinyl ether, and their corresponding radicals . J. Phys. Chem. A , 110 , 7925 – 7934 .
   PubMed Web of Science ®Google Scholar
• Foresman , J.B. and Frisch , A. ( 1993 ) Exploring Chemistry with Electronic Structure Methods: A Guide to Using Gaussian, , 1st ed. , Gaussian , Pittsburg , Pa .
   Google Scholar
• Frisch , M.J. , Trucks , G.W. , Schlegel , H.B. , Scuseria , G.E. , Robb , M.A. , Cheeseman , J.R. , Zakrzewski , V.G. , Montgomery , J.A. , Jr. , Stratmann , R.E. , Burant , J.C. , Dapprich , S. , Millam , J.M. , Daniels , A.D. , Kudin , K.N. , Strain , M.C. , Farkas , O. , Tomasi , J. , Barone , V. , Cossi , M. , Cammi , R. , Mennucci , B. , Pomelli , C. , Adamo , C. , Clifford , S. , Ochterski , J. Petersson , G.A. , Ayala , P.Y. , Cui , Q. , Morokuma , K. , Salvador , P. , Dannenberg , J.J. , Malick , D.K. , Rabuck , A.D. , Raghavachari , K. , Foresman , J.B. , Cioslowski , J. , Ortiz , J.V. , Baboul , A.G. , Stefanov , B.B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Gomperts , R. , 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. , Andres , J.L. , Gonzalez , C. , Head-Gordon , M. , Replogle , E.S. , and Pople , J.A. 2001 . Gaussian 98, Gaussian, Inc. , Pittsburgh , PA , (Revision A.11) .
   Google Scholar
• Guthrie , G.B. , Jr., Scott , D.W. , Hubbard , W.N. , Katz , C. , McCullough , J.P. , Gross , M.E. , Williamson , K.D. , and Waddington , G. ( 1952 ) Thermodynamic properties of furan . J. Am. Chem. Soc. , 74 ( 18 ), 4662 – 4669 .
   Google Scholar
• <http://www.gaussian.com/index.htm> . The official Gaussian website , last update: 4 March 2008 .
   Google Scholar
• Knyazev , V.D. and Slagle I.R. ( 1998 ) Thermochemistry of the R=O2 bond in alkyl and chloroalkyl peroxy radicals . J. Phys. Chem. A , 102 , 1770 – 1778 .
   Google Scholar
• Lay , T.H. , Krasnoperov , L.N. , Venanzi , C.A. , and Bozzelli , J.W. ( 1996 ) Ab Initio study of cc-chlorinated ethyl hydroperoxides CH3CH2OOH, CH3CHClOOH, and CH3CCl2OOH: Conformational analysis, internal rotation barriers, vibrational frequencies, and thermodynamic properties . J. Phys. Chem. , 100 , 8240 – 8249 .
   Google Scholar
• Lee , C. , Yang , W. , and Parr , R.G. (1988) Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. , B 37, 785–789.
   Web of Science ®Google Scholar
• Mayer , P.M. , Parkinson , O.J. , Smith , D.M. , and Radom , L. ( 1998 ) An assessment of theoretical procedures for the calculation of reliable free radical thermochemistry: A recommended new procedure . J. Chem. Phys. , 108 , 604 – 615 .
   Web of Science ®Google Scholar
• Mebel , A.M. , Diau , E.W.G. , Lin , M.C. , and Morokuma , K. ( 1996 ) Ab initio and RRKM calculations for Multichannel rate constants of the C2H3 + O2 reaction . J. Am. Chem. Soc. , 118 , 9759 – 9771 .
   Web of Science ®Google Scholar
• Mebel , A.M. and Kislov , V.V. ( 2005 ) The C2H3 + O2 reaction revisted: Is multi reference treatment of the wave function really critical? J. Phys. Chem. A. , (Letter) , 109 ( 32 ), 6993 – 6997 .
   PubMedGoogle Scholar
• Montgomery , J.A. , Ocherski , J.W. and Petersson , G.A. ( 1994 ) A complete basis set model chemistry. IV. An improved atomic pair natural orbital method . J. Chem. Phys. , 101 , 5900 – 5909 .
   Web of Science ®Google Scholar
• Petersson , G.A. , Malick , D.K. , and Wilson , W.G. ( 1998 ) Calibration and comparison of the Gaussian-2, complete basis set, and density functional methods for computational thermochemistry . J. Chem. Phys. , 109 , 10570 – 10579 .
   Web of Science ®Google Scholar
• Prosen , E.J. and Rossini , F.D. ( 1945 ) Heats of combustion and formation of the paraffin hydrocarbons at 25°C . J. Res. NBS , 263 – 267 .
   Google Scholar
• Prosen , E.J. , Gilmont , R. , and Rossini , F.D. ( 1945 ) Heats of combustion of benzene, toluene, ethyl-benzene, O-xylene, m-xylene, p-xylene, n-propylbenzene, and styrene . J. Res. NBS , 34 , 65 – 70 .
   Google Scholar
• Redfern , P.C. , Zapol , P. , Curtiss , L.A. , and Raghavachari , K. ( 2000 ) Assessment of Gaussian-3 and density functional theories for enthalpies of formation of C1=C16 alkanes . J. Phys. Chem. A , 104 , 5850 – 5854 .
   Web of Science ®Google Scholar
• Ruscic , B. , Feller , D. , Dixon , D.A. , Peterson , K.A. , Harding , L.B. , Asher , R.L. , and Wagner , A.F. ( 2001 ) Evidence for a lower enthalpy of formation of hydroxyl radical and a lower gas-phase bond dissociation energy of water . J. Phys. Chem. A , 105 , 1 – 4 .
   Web of Science ®Google Scholar
• Ruscic , B. , Pinzon , R.E. , Morton , M.L. , Srinivasan , N.K. , Su , M.-C. , Sutherland , J.W. , and Michael , J.V. ( 2006 ) Active thermochemical tables: Accurate enthalpy of formation of hydroperoxyl radical, HO2 . J. Phys. Chem. A , 110 , 6592 – 6601 .
   PubMed Web of Science ®Google Scholar
• Sabbah , R. ( 1991 ) Thermodynamic study of fluorene and dibenzofuran . Bull. Soc. Chim. Fr. , 128 , 350 .
   Google Scholar
• Sebbar , N. , Bockhorn , H. , and Bozzelli . J.W. ( 2001 ) Thermodynamic properties (Enthalpies, entropies and heat capacities) and reactions of vinyl hydroperoxides, peroxy radicals and phenyl hydroperoxides . 5th International Conference on Chemical Kinetics , 16–20 July , National Institute of standards and Technologies , Gaithersburg , MD , USA .
   Google Scholar
• Sebbar , N. Bockhorn , H. , and Bozzelli , J.W. ( 2002a ) Structures, thermochemical properties (Enthalpy, entropy and heat capacity), Rotation barriers, bond energies of vinyl, allyl, ethynyl and phenyl hydroperoxides . Phys. Chem. Chem. Phys. , 4 , 3691 – 3703 .
   Google Scholar
• Sebbar , N. , Bockhorn , H. , Chen , C.-J. , and Bozzelli , J.W. ( 2002b ) Reaction of phenyl radical with O₂: Thermodynamic properties, reaction pathways and kinetics . 17th International Symposium on Gas Kinetics , Essen , August , pp. 24 – 29 .
   Google Scholar
• Sebbar , N. , Bockhorn , H. , and Bozzelli . J.W. ( 2003a ) Reaction of dibenzofuran radical with O2: Thermodynamic properties, reaction pathways and kinetics . The 8th International Congress on Combustion by Products: Origin, Fate and Health Impacts , Umeå , Sweden , June 17–19 .
   Google Scholar
• Sebbar , N. , Bockhorn , H. , and Bozzelli . J.W. ( 2003b ) Reaction of dibenzofuran radical with O2 . Proceeding of the European Combustion Meeting 2003 , Orléans , France , October 25 .
   Google Scholar
• Sebbar , N. , Bockhorn , H. , and Bozzelli , J.W. ( 2005a ) Thermochemical properties, rotation barriers, and group additivity for unsaturated oxygenated hydrocarbons and radicals resulting from reaction of Vinyl and phenyl radical systems with O2 . J. Phys. Chem. A , 109 , 2233 – 2253 .
   PubMed Web of Science ®Google Scholar
• Sebbar , N. , Bockhorn , H. , and Bozzelli , J.W. (2005b) Enthalpy of formation and bond energies on unsaturated oxygenated hydrocarbons using G3MP2B3 calculation methods. Int. J. Chem. Kinet. , 37, 633–648.
   Web of Science ®Google Scholar
• Sebbar , N. , Bockhorn , H. , and Bozzelli , J.W. ( 2008 ) Thermodynamic properties of the species resulting from the phenyl radical with O2 reaction system . Int. J. Chem. Kinet. in press .
   Google Scholar
• Steele , W.V. and Chirico , R.D. ( 1990 ) Thermodynamics and the hydrodeoxygenation of 2,3-benzofuran, IIT. Thermodynamics and the Hydrodeoxygenation of 2,3-benzofuran, IIT Research Institute , NIPEP , Bartlesville , OK 74005 , pp. 1 – 75 .
   Google Scholar
• Shokhirev N http://www.chem.arizona.edu/faculty/walk/nikolai/programs.html#programs.
   Google Scholar
• Tokmakov , I.V. , Kim , G.-S. , Kislov , V.V. , Mebel , A.M. , and Lin , M.C. ( 2005 ) The reaction of phenyl radical with molecular oxygen: A G2M study of the potential energy surface . J. Phys.Chem. A , 109 , 6114 – 6127 .
   PubMedGoogle Scholar
• Tsang , W. , Martinho Simoes , J.A. , Greenberg , A. , and Liebman , J.F. ( 1996 ) Heats of Formation of Organic Free Radicals by Kinetic Methods Energetics of Organic Free Radicals eds. , Blackie Academic and Professional , London , pp. 22 – 58 .
   Google Scholar
• Turecek , F. and Havlas , Z. ( 1986 ) Thermochemistry of unstable ends: The O-(Cd) (H) group equivalent . J. Org. Chem. , 51 , 4066 – 4067 .
   Google Scholar
• Wong , M.W. and Radom , L. ( 1998 ) Radical addition to alkenes: Further assessment of theoretical procedures . J. Phys. Chem. , 102 , 2237 – 2245 .
   Web of Science ®Google Scholar
• Yamada , T. , Lay , T.H. , and Bozzelli , J.W. ( 1998 ) Ab initio calculations and internal rotor: Contribution for thermodynamic properties S298 and Cp (T)'S (3000 < T/K < 1500): Group additivity for fluoroethanes . J. Phys. Chem. A. , 102 , 7286 – 7293 .
   Web of Science ®Google Scholar
• Yamada , T. , Lay , T. H. , and Bozzelli , J.W. ( 1999 ) Thermodynamic properties (ΔHf(298), S(298), and Cp(T) (300 ≤ T ≤ 1500)) of fluorinated propanes . J. Phys Chem. A , 103 , 5602 – 5610 .
   Google Scholar