Evaluation of C-H bond dissociation energies in hydrocarbons and the enthalpies of the relevant radicals from kinetic data

Petroleum Chemistry

Volumn 41, Issue 2, 2001, Pages 93-102

  Tumanov, V E ^a   Denisov, E T ^a  

^a INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOALKANE DERIVATIVE; HYDROCARBON;

ARTICLE; CHEMICAL BOND; DISSOCIATION; ENERGY; ENTHALPY; MATHEMATICAL ANALYSIS; MOLECULAR MODEL; PHYSICAL CHEMISTRY; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0035297133     PISSN: 09655441     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. McMillen, D.F. and Golden, D.M., Hydrocarbon Bond Dissociation Energies, Ann. Rev. Phys. Chem., 1982, vol. 33, p. 493.
2. Tsang, W., Heats of Formation of Organic Free Radicals by Kinetic Methods., Energetics of Free Radicals, Greenberg, A. and Liebmar, J., Eds., New York: Blackie Academic and Professional, 1996, p. 22.
3. Berkowitz, J., Ellison, G.B., and Gutman, D., Three Methods to Measure RH Bond Energies, J. Phys. Chem., 1994, vol. 98, p. 2744.
4. Denisov, E.T., Evaluation of Hydrocarbon C-H Bond Dissociation Energies from Rate Constants of Radical Reactions, Zh. Fiz. Khim., 1993, vol. 67, no. 12, p. 2416.
5. Denisov, E.T., New Empirical Models for the Radical Abstraction Reaction, Usp. Khim., 1997, vol. 66, no. 10, p. 953.
6. Tumanov, V.E., Software for the Rate Constant Database of Radical Liquid-Phase Reactions, Preprint of Inst. Chem. Phys., Russ. Acad. Sci., Chernogolovka, 1993.
7. Tumanov, V.E. and Denisov, E.T., Evaluation of Hydrocarbon C-H Bond Dissociation Energies from Rate Constants of Radical Reactions in Terms of the Model of Crossing Morse Curves, Zh. Fiz. Khim., 1995, vol. 69, no. 9, p. 1572.
8. Redley, J.B. and Rylance, J., Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, Brighton: Univ. of Sussex, 1977.
9. Domalski, E.S. and Hearing, E.D., Estimation of the Thermodynamic Properties of C-H-O-S-Halogen Compounds at 298.15 K, J. Phys. Chem. Ref. Data, 1993, vol. 22, no. 4, p. 805.
10. NIST Standard Reference Database 19A: Positive Ion Energetics. Ver. 2.02, 1994.
11. Pritzkow, W.W. and Suprun, V.Ya., Reactivity of Hydrocarbons and Their Individual Bonds in Oxidation Processes Involving Peroxy Radicals, Usp. Khim., 1996, vol. 65, no. 6, p. 538.
12. Neta, P., Fessenden, R.W., and Schuler, R.H., An Electron Spin Resonance Study of the Rate Constants for Reaction of Hydrogen Atoms with Organic Compounds in Aqueous Solution, J. Phys. Chem., 1971, vol. 75, no. 11, p. 1654.
13. Mallard, W.G., Westley, F., Herron, J.T., and Hampson, R.F., NIST Chemical Kinetics Database, - Ver. 6.0, NIST Standard Reference Data, Gaithersburg, Md., 1994.
14. Hawari, J.A., Davis, S., Engel, P.S., Gilbert, B.C., and Griller, D., The Free Radical Reaction between Alkanes and Carbon Tetrachloride, J. Am. Chem. Soc., 1985, vol. 107, no. 16, p. 4721.
15. Chenier, J.H.B., Tong, S.B., and Howard, J.A., Absolute Rate Constants for Hydrocarbon Autoxidation: 25. Rate Constants for Hydrogen Atom Abstraction from Alkanes by the tert-Bytylperoxy Radical, Can. J. Chem., 1978, vol. 56, no. 24, p. 3047.
16. DeTar, D.F. and Wells, D.V., The Reactivity of the 1-Hexyl Radical in Abstracting Hydrogen and Halogen Atoms, J. Am. Chem. Soc., 1960, vol. 82, no. 22, p. 5839.
17. Korcek, S., Chenier, J.H.B., Howard, J.A., and Ingold, K.U., Absolute Rate Constants for Hydrocarbon Autooxidation: 21. Activation Energies for Propagation and Correlation of Propagation Rate Constants with C-H Bond Strengths, Can. J. Chem., 1972, vol. 50, no. 14, p. 2285.
18. Bridger, R.F. and Russel, G.A., Directive Effects in the Attack of Phenyl Radicals on Carbon-Hydrogen Bonds, J. Am. Chem. Soc., 1963, vol. 85, no. 23, p. 3754.
19. Alfassi, Z.B. and Feldman, L., The Kinetics of Radiation Induced Hydrogen Abstraction by CCII Radicals in the Liquid Phase: Cyclanes, Int. J. Chem. Kinet., 1981, vol. 13, no. 6, p. 517.
20. Harnish, R., Lauterbach, G., and Pritzkow, W., Kinetics of Peroxyradical Attack at Cyclic Hydrocarbons: Ring-Strain Effects on H-Abstraction, J. Prakt. Chem., 1995, vol. 337, p. 60.
21. Berezin, I.V. and Dobish, O., Effect of Structure and Environment on the Reactivity of Hydrocarbons in Liquid-Phase Reactions with Methyl Radicals, Dokl. Akad. Nauk SSSR, 1962, vol. 144, no. 62, p. 374.
22. Lauterbach, G. and Pritzkow, W., Competitive Oxidation of cis/trans Isomeric Derivatives of Cyclohexane with Cumene: Relative Reactivities of Axial and Equatorial Tertiary C-H-Bonds // J. Prakt. Chem., 1994, vol. 336, p. 83.
23. Dobish, O., Reactivity of Hydrocarbons in Reactions with Methyl Radicals, Cand. Sci. (Chem.) Dissertation, Moscow: Moscow State Univ., 1962.
24. Wong, P.C., Griller, D., and Scaiano, J.C., A Kinetic Study of the Reactions of tert-Butoxyl with Alkenes: Hydrogen Abstraction vs. Addition, J. Am. Chem. Soc., 1982, vol. 104, no. 19, p. 5106.
25. Parlant, C., Seree de Roch, I., and Balaceanu, J.C., Oxydation du cyclohexanol en phase liquide par l'oxygene moleculaire, Bull. Soc. Chim. Fr., 1963, no. 11, p. 2452.
26. Brook, J., H-Reaction of Hydrocarbons with tert-Butoxy Radicals, Trans. Faraday Soc., 1957, vol. 53, no. 411(3), p. 327.
27. Walling, C. and Thaler, W., Positive Halogen Compounds: Allylic Chlorination with t-Butyl Hypochlorite: The Stereochemistry of Allylic Radicals, J. Am. Chem. Soc., 1961, vol. 83, no. 18, p. 3877.
28. Stefani, A.P. and Szwarc, M., Kinetic of Addition of CFI Radicals to Olefins and Their Derivatives, J. Am. Chem. Soc., 1961, vol. 83, no. 23, p. 4732.
29. Koelewijn, P., Epoxidation of Olefins by Alkylperoxy Radicals, Recl. Trav. Chim. Pays-Bas, 1972, vol. 91, no. 6, p. 759.
30. Encina, M.V. and Scaing, J.C., Reaction of Benzophenone Triplets with Allylic Hydrogens: A Laser Flash Photolysis Study, J. Am. Chem. Soc., 1981, vol. 103, no. 21, p. 6393.
31. Paul, H., Small, R.D., Jr., and Scaiano, J.C., Hydrogen Abstraction by tert-Bytoxy Radicals: A Laser Photolysis and Electron Spin Resonance Study, J. Am. Chem. Soc., 1978, vol. 100, no. 14, p. 4520.
32. Kooyman, E.C., Structural Factors Governing the Reactivities of Alpha-Methylenic Groups toward Active Free Radicals, Disc. Faraday Soc., 1951, no. 10, p. 163.
33. Howard, J.A. and Ingold, K.U., Symonds M Absolute Rate Constants for Hydrocarbon Oxidation: 8. The Reactions of Cumylperoxy Radicals, Can. J. Chem., 1968, vol. 46, no. 6, p. 1017.
34. Stefani, A.P., Chuang, L.Y., and Todd, H.E., Relative Rates of Addition of Cyclopropyl Radicals to Olefins, J. Am. Chem. Soc., 1970, vol. 92, no. 14, p. 4168.
35. Lauterbach, G. and Pritzkow, W., Kinetics and Regioselectivity of the Autoxidation of Monocyclic Olefins and Bicyclo [2.2.1]heptene, J. Prakt. Chem., 1995, vol. 337, p. 237.
36. Robb, J.C. and Shahin, M.A., A Thermocouple Method of Studying Oxidation Reactions: 2. Photosensitized Oxidation of 1-Methyl-, 4-Methyl- and 4,5-Dimethylcyclohexene, Trans. Faraday Soc., 1959, vol. 55, no. 442(10), p. 1753.
37. Howard, J.A. and Ingold, K.U., Absolute Rate Constants for Hydrocarbon Autoxidation: 3. α-Methylstyrene, β-Methylstyrene and Indene, Can. J. Chem., 1966, vol. 44, no. 10, p. 1113.
38. Effio, A., Criller, D., Ingold, K.U., Scaiano, J.C., and Sheng, S.J., Studies on the Spiro[2.5]octadienyl Radical and the 2-Phyenylethyl Rearrangement, J. Am. Chem. Soc., 1980, vol. 102, no. 19, p. 6063.