A new method for estimation of homolytic C-H bond dissociation enthalpies

Journal of Chemical Information and Computer Sciences

Volumn 40, Issue 5, 2000, Pages 1222-1226

  Cherkasov, Artem ^a,b   Jonsson, Mats ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000539877     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci000387p     Document Type: Article

References (35)

1. Pauling, L. The Nature of the Chemical Bond, 3rd ed., Cornell University Press: Ithaca, NY, 1960.
2. Sanderson, R. T. Chemical Bonds and Bond Energy, Academic: New York, 1976.
3. Sanderson, R. T. Polar Covalence; Academic: New York, 1983.
4. Cohen, N.; Benson, S. W. Estimation of Heats of Formation of Organic Compounds by Additivity Methods. Chem. Rev. 1993, 93, 2419.
5. Smith, D. W. Additive bond-energy scheme with geminal H-H terms. Applications to the enthalpies of formation of alkane derivatives. J. Chem. Soc., Faraday Trans. 1997, 93, 2037.
6. Cherkasov, A.; Jonsson, M. Substituent Effects on Thermochemical Properties of Free Radicals. New Substituent Scales for C-Centered Radicals. J. Chem. Inf. Comput. Sci. 1998, 38, 1151.
7. Cherkasov, A.; Jonsson, M. Substituent Effects on Thermochemical Properties of C-, N-, O- and S-Centered Radicals. Physical Interpretation of Substituent Effects. J. Chem. Inf. Comput. Sci. 1999, 39, 1057.
8. Cherkasov, A. R.; Jonsson, M.; Galkin, V. A novel approach to the analysis of substituent effects: Quantitative description of ionization energies and gas basicity of amines. J. Mol. Graphics Mod. 1999, 17, 28.
9. Galkin, V. I.; Sayakhov, R. D.; Cherkasov, R. A. Steric Effect: The Problem of Quantitative Estimation and Appearance in the Reactivity of Organoelement Compounds. Usp. Khim. (Russ. Chem. Rev.) 1991, 60, 1617.
10. Cherkasov, A. R.; Galkin, V. I.; Cherkasov, R. A. A New Approach to Theoretical Estimation of Inductive Constants. J. Phys. Org. Chem. 1998, 11, 437.
11. Berkowitz, J.; Ellison, G. B.; Gutman, D. Three Methods To Measure RH Bond Energies. J. Phys. Chem. 1994, 98, 2744.
12. McMillen, D. F.; Golden, D. M. Hydrocarbon Bond Dissociation Energies. Annu. Rev. Phys. Chem. 1982, 33, 493.
13. Castelhano, A. L.; Griller, D. Heats of Formation of some Simple Hydrocarbons J. Am. Chem. Soc. 1982, 104, 3655.
14. Trenwith, B.; Wrigley, S. P. Dissociation of 2-Methyl But-1-ene and the Resonance Energy of the 2-Methyl Allyl Radical. J. Chem. Soc., Faraday Trans. 1 1977, 73, 817.
15. Tsang, W. Pyrolysis of 2,4-Dimethylhexene-1 and the Stability of Isobutenyl Radicals. Int. J. Chem. Kinet. 1973, 5, 929.
16. Wayner, D. D. M.; Clark, K. B.; Rauk, A.; Yu, D.; Armstrong, D. A. C-H Bond Dissociation Energies of Alkylamines: Radical Structures and Stabilization Energies. J. Am. Chem. Soc. 1997, 119, 8925.
17. Jefferson, A.; Nicovich, J. M.; Wine, P. H. Temperature-Dependent Kinetics Studies of the Reactions Br(P-2(3/2))+CH3SCH3 ↔ CH3SCH2+HBr. Heat of Formation of the CH3SCH2 Radical. J. Phys. Chem. 1994, 98, 7128.
18. Trenwith, A. B. Dissociation of 3-Methylpenta-1,4-diene and the Resonance Energy of the Pentadienyl Radical. J. Chem. Soc., Faraday Trans. 1 1982, 78, 3131.
19. Handbook of Chemistry and Physics, 78th ed.: CRC Press: Boca Raton, FL, 1997-1998.
20. Rossi, M.; McMillen, D. F.; Golden, D. M. Aliphatic CH Bond Scission Processes in Diphenylmethane and 2-Benzyl- and 4-Benzylpyridine. The Heat of Formation of the Diphenylmethyl and α-Phenylethyl Radical in the Gas-Phase. J. Phys. Chem. 1984, 88, 5031.
21. Kondo, O.; Benson, S. W. Kinetics and Equilibria of the Reaction between Bromine and Ethyl Ether. Int. J. Chem. Kinet. 1984, 16, 949.
22. Pickard, J. M.; Rodgers, A. S. Kinetics of the Gas-Phase Reaction CH3F + 12 = CH2FI + HI. The CH Bond Dissociation Energy in Methyl and Methylene Fluorides. Int. J. Chem. Kinet. 1983, 15, 569.
23. Tschuikow-Roux, E.; Paddison, S. Bond Dissociation Energies and Radical Heats of Formation in CH3Cl, CH2Cl2, CH3Br, CH2Br2, CH2FCl and CHFCl2. Int. J. Chem. Kinet. 1987, 19, 15.
24. Miyokawa, K.; Tschuikow-Roux, E. Reaction of Atomic Bromine with Difluorochloromethane. The Heat of Formation of the CClF2 Radical and the Do(CClF2-H) Bond Dissociation Energy. J. Phys. Chem. 1992, 96, 7328.
25. Hudgens, J. W.; Johnson, R. D.; Timonen, R. S.; Seetula, J. A.; Gutman, D. Kinetics of the Reaction of CC13 + Br2 and Thermochemistry of CC13 Radical and Cation. J. Phys. Chem. 1991, 95, 4400.
26. Evans, S.; Weeks, I.; Whittle, E. Bromination of Fluoroalkanes. J. Chem. Soc., Faraday Trans. 1 1983, 79, 1471.
27. Walsh, R. Bond Dissociation Energy Values in Silicon Containing Compounds and Some of Their Implications. Acc. Chem. Res. 1981, 14, 246.
28. Yu, D.; Rauk, A.; Armstrong, D. A. Radicals and ions of formic and acetic acids: an ab initio study of the structures and gas and solution phase thermochemistry. J. Chem. Soc., Perkin Trans. 2 1994, 2207.
29. Yu, D.; Rauk, A.; Armstrong, D. A. Radicals and Ions of Glycine: An ab Initio Study of the Structures and Gas-Phase Thermochemistry. J. Am. Chem. Soc. 1995, 117, 1789.
30. Jonsson, M.; Wayner, D. D. M.; Armstrong, D. A.; Yu, D.; Rauk, A. On the thermodynamics of peptide oxidation: anhydrides of glycine and alanine. J. Chem. Soc., Perkin Trans. 2 1998, 1967.
31. Armstrong, D. A.; Rauk, A.; Yu, D. Oxidative damage to the glycyl α-carbon site in proteins: an ab initio study of the C-H bond dissociation energy and the reduction potential of the C-centered radical. Can. J. Chem. 1996, 74, 1192.
32. Rauk, A.; Yu, D.; Armstrong, D. A. Toward Site Specificity of Oxidative Damage in Proteins: C-H and C-C Bond Dissociation Energies and Reduction Potentials of the Radicals of Alanine, Serine, and Threonine Residues - An ab Initio Study. J. Am. Chem. Soc. 1997, 119, 208.
33. Clark, K. B.; Wayner, D. D. M.; Demirdji, S. H.; Koch, T. H. Bond-Dissociation Energies of 3,5,5-Trimethyl-2-oxomorpholines and 4,5,5-Trimethyl-2- oxomorpholines by Photoacoustic Calorimetry - an Assessment of the Additivity of Substituent Effects J. Am. Chem. Soc. 1993, 115, 2447.
34. Calculated from data taken from NIST Standard Reference Database No. 69, November 1998 Release.
35. Streitwieser, A., Jr.; Heathcock, C. H. Introduction to Organic Chemistry; Macmillan Publishing Company: New York, 1989; p 1152.