Cycloalkane and cycloalkene C-H bond dissociation energies

Journal of the American Chemical Society

Volumn 128, Issue 51, 2006, Pages 17087-17092

  Tian, Zhixin ^a   Fattahi, Alireza ^a   Lis, Lev ^a   Kass, Steven R ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND DISSOCIATION ENERGIES; ELECTRON BINDING ENERGY; PROTON AFFINITY; THERMODYNAMIC CYCLES;

BINDING ENERGY; CHEMICAL BONDS; DISSOCIATION; OLEFINS; REACTION KINETICS; THERMODYNAMICS;

PARAFFINS;

1 CYCLOBUTENE; 3 CYCLOBUTENE; BUTANE; CARBON; CYCLOALKANE DERIVATIVE; CYCLOALKENE; CYCLOBUTADIENE; CYCLOBUTANE; CYCLOBUTENE DERIVATIVE; CYCLOHEXANE; CYCLOPROPANE; HYDROGEN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; DISSOCIATION; ELECTRON TRANSPORT; ENERGY TRANSFER; GAS ANALYSIS; MATHEMATICAL COMPUTING; PHASE TRANSITION; PROTON TRANSPORT; THERMODYNAMICS;

EID: 33845942250     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065348u     Document Type: Article

References (48)

1. (a) Energetics of Organic Free Radicals; Simões, J. A. M., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic & Professional: New York, 1996; p 301.
2. (b) Parsons, A. F. An Introduction to Free Radical Chemistry; Blackwell Science: Oxford, England, 2000; p 238.
3. (c) Finlayson-Pitts, B. J. Chemistry of the Upper and Lower Atmosphere: Theory, Experiments and Applications; Academic Press: San Diego, CA, 2000; p 969.
4. (d) Côme, G.-M. Gas-Phase Thermal Reactions: Chemical Engineering Kinetics; Kluwer Academic Publishers: Boston, MA, 2001; p 336.
5. Fattahi, A.; McCarthy, R. E.; Ahmad, M. R.; Kass, S. R. J. Am. Chem. Soc. 2003, 125, 11746-11750.
6. DeFrees, D. J.; McIver, R. T., Jr.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 3334-3338.
7. (a) Chen, P. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 2, pp 45-75.
8. (b) Merrill, G. N.; Kass, S. R. J. Am. Chem. Soc. 1997, 119, 12322-12337.
9. (c) Montgomery, J. A., Jr.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1994, 101, 5900-5909.
10. (d) Bach, R. D.; Dmitrenko, O. J. Am. Chem. Soc. 2004, 126, 4444-4452.
11. (e) Feng, Y.; Liu, L.; Wang, J.-T.; Zhao, S.-W.; Guo, Q.-X. J. Org. Chem. 2004, 69, 3129-3138.
12. Fattahi, A.; Lis, L.; Tian, Z.; Kass, S. R. Angew. Chem., Int. Ed. 2006, 45, 4984-4988.
13. Furuyama, S.; Golden, D. M.; Benson, S. W. Int. J. Chem. Kinet. 1970, 2, 93-99.
14. Alfassi, Z. B.; Feldman, L. Int. J. Chem. Kinet. 1981, 13, 771-783.
15. a's and BDEs also was needed to obtain the desired bond energy, and a change in one of the BDEs would have a large effect on the final result.
16. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764-7776.
17. (a) Martin, J. M. L.; de Oliveria, G. J. Chem. Phys. 1999, 111, 1843-1856.
18. (b) Parthiban, S.; Martin, J. M. L. J. Chem. Phys. 2001, 114, 6014-6029.
19. Graig, N. C.; Borick, S. S.; Fisher, M. A.; Tucker, T. R.: Xiao, Y.-Z. J. Fluorine Chem. 1992, 59, 215-224.
20. Negishi, E.; Boardman, L. D.; Sawada, H.; Bagheri, V.; Stoll, A. T.; Tour, J. M.; Rand, C. L. J. Am. Chem. Soc. 1988, 110, 5383-5396.
21. Wang, T. C. L.; Ricca, T. L.; Marshall, A. G. Anal. Chem. 1986, 58, 2935-2938.
22. (a) DePuy, C. H.; Gronert, S.; Barlow, S. E.; Bierbaum, V. M.; Damrauer, R. J. Am. Chem. Soc. 1989, 111. 1968-1973.
23. (b) DePuy, C. H.; Bierbaum, V. M.; Damrauer, R. J. Am. Chem. Soc. 1984, 106, 4051-4053.
24. Pople, J. A.; et al. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
25. Bartmess, J. E. NIST Chemistry WebBook, NIST Standard Reference Database Number 69, Mallard, W. G., Linstrom, P. J., Eds. http://webbook.nist.gov; Oct 2006.
26. acid.
27. The cited values are at the B3LYP/aug-cc-pVTZ level.
28. Fattahi, A.; Kass, S. R. J. Org. Chem. 2004, 69, 9176-9183.
29. Kass, S. R.; Filley, J.; Van Doren, J. M.; DePuy, C. H. J. Am. Chem. Soc. 1986, 108, 2849-2852.
30. -1, as given in ref 2.
31. Hill, E. A.; Roberts, J. D. J. Am. Chem. Soc. 1967, 89, 2047-2049.
32. -1.
33. - because it is a delocalized ion whereas the reference compounds correspond to localized species.
34. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res, 2003, 36, 255-263.
35. CRC Handbook of Chemistry and Physics, 85th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2004.
36. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493-532.
37. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003.
38. Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: New York, 1970; p 643.
39. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: New York, 1986; p 792.
40. Tsang, W. In Energetics of Stable Molecules and Reactive Intermediates; Minas da Piedade, M. E., Ed.; NATO Science Series C535; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 323-352.
41. Baghal-Vayjooee, M. H.; Benson, S. W. J. Am. Chem. Soc. 1979, 101, 2838-2840.
42. (a) McMillen, D. F.; Golden, D. M.; Benson, S. W. Int. J. Chem. Kinet. 1972, 4, 487-495.
43. (b) Ferguson, K. C.; Whittle, E. Trans. Faraday Soc. 1971, 67, 2618-2628.
44. Tsang, W. In Shock Waves in Chemistry; Lifshitz, A., Ed.; Marcel Dekker: New York, 1981; pp 59-129.
45. These values come from population analyses of B3LYP/cc-pvtz+d wave-functions, but similar results are obtained from HF and MP2 calculations.
46. (a) Parr, A. C.; Elder, F. A. J. Chem. Phys. 1968, 49, 2659-2664.
47. (b) Parr, A. C.; Jason, A. J.; Stockbauer, R. Int. J. Mass Spectrom. Ion Phys. 1978, 26, 23-28.
48. (c) Parr, A. C.; Jason, A. J.; Stockbauer, R. Int. J. Mass Spectrom. Ion Phys. 1980, 33, 243-251.