Substituent effects on the reaction rates of hydrogen abstraction in the pyrolysis of phenethyl phenyl ethers

Energy and Fuels

Volumn 24, Issue 5, 2010, Pages 2857-2867

  Beste, Ariana ^a   Buchanan, A C ^a  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANHARMONIC CORRECTION; ARYL ETHER; COMPUTATIONAL ANALYSIS; CONFORMATIONAL SPACE; FORWARD RATE CONSTANTS; HOMOLYSIS; HYDROGEN ABSTRACTION; HYDROGEN ABSTRACTION REACTION; HYDROGEN-TRANSFER REACTIONS; INDEPENDENT MODE; KINETIC MODELS; METHOXY; PHENOXY RADICALS; PHENYL ETHERS; PHENYL RINGS; POLAR EFFECT; PRODUCT SELECTIVITIES; PYROLYSIS MECHANISM; QUASI STEADY STATE CONDITIONS; REACTION PROFILE; SUBSTITUENT EFFECT; TRANSITION STATE THEORIES;

ABSTRACTING; DENSITY FUNCTIONAL THEORY; ETHERS; HYDROGEN; ORGANIC COMPOUNDS; OXYGEN; PYROLYSIS; THERMOGRAVIMETRIC ANALYSIS;

RATE CONSTANTS;

EID: 77952693269     PISSN: 08870624     EISSN: 15205029     Source Type: Journal    
DOI: 10.1021/ef1001953     Document Type: Article

References (31)

1. Mohan, D.; Pittman, C. U., Jr.; Steele, P. H. Energy Fuels 2006, 20, 848
2. Suhas Carrott, P. J. M.; Ribeiro Carrott, M. M. L. Bioresour. Technol. 2007, 98, 2301
3. Baumling, S.; Broust, F.; Bazer-Bachi, F.; Bourdeaux, T.; Herbinet, O.; Ndiaye, F. T.; Ferrer, M.; Lédé, J. Int. J. Hydrogen Energy 2006, 31, 2179
4. Beste, A; Buchanan, A. C., III; Britt, P. F.; Hathorn, B. C.; Harrison, R. J. J. Phys. Chem. A 2007, 111, 12118
5. Kawamoto, H.; Horigoshi, S.; Saka, S. J. Wood Sci. 2007, 53, 168
6. Kawamoto, H.; Horigoshi, S.; Saka, S. J. Wood Sci. 2007, 53, 268
7. Britt, P. F.; Buchanan, A. C., III; Malcolm, E. A. J. Org. Chem. 1995, 60, 6523
8. Britt, P. F.; Kidder, M. K.; Buchanan, A. C., III Energy Fuels 2007, 21, 3102
9. Britt, P. F.; Buchanan, A. C., III; Cooney, M. J.; Martineau, D. R. J. Org. Chem. 2000, 65, 1376
10. Simon, J. P.; Eriksson, K.-E. L. J. Mol. Struct. 1996, 384, 1
11. Agache, C.; Popa, V. I. Chem. Mon. 2006, 137, 55
12. Elder, T. Biomacromolecules 2007, 8, 3619
13. Da Silva, G.; Bozzelli, J. W. J. Chem. Phys. A 2007, 111, 7987
14. Beste, A.; Buchanan, A. C., III J. Org. Chem. 2009, 74, 2837
15. Chen, X.; Zhang, X.; Han, K.; Varandas, A. J. C. Chem. Phys. Lett. 2006, 421, 453
16. Wang, W.; Feng, L.; Wang, W.; Luo, Q.; Li, Q. J. Mol. Struct. 2006, 764, 53
17. Phillips, D. L.; Zhao, C.; Wang, D. J. Phys. Chem. A 2005, 109, 9653
18. Zhang, Y.; Li, Q. S.; Zhang, S. J. Mol. Struct. 2004, 682, 163
19. Chan, W.-T.; Hamilton, I. P.; Pritchard, H. O. J. Chem. Soc., Faraday Trans. 1998, 19, 2303
20. Garrett, B. C.; Truhlar, D. G. J. Chem. Phys. 1979, 70, 1593
21. Garrett, B. C.; Truhlar, D. G. J. Am. Chem. Soc. 1979, 101, 4534
22. Wigner, E. P. Phys. Rev. 1932, 40, 749
23. Kirkwood, J. G. Phys. Rev. 1933, 44, 31
24. Beste, A.; Buchanan, A. C.; Harrison, R. J. J. Phys. Chem. A 2008, 112, 4982
25. Kendall, R. A.; Apra, E.; Bernholdt, D. E.; Bylaska, E. J.; Dupuis, M.; Fann, G. I.; Harrison, R. J.; Ju, J. L.; Nichols, J. A.; Nieplocha, J.; Straatsma, T. P.; Windus, T. L.; Wong, A. T. Comput. Phys. Commun. 2000, 128, 260
26. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
27. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2008, 4, 1849
28. Henriksen, N. E.; Hansen, F. Y. Theory of Molecular Reaction Dynamics; Oxford University Press: New York, 2008; pp 153 - 155.
29. Donahue, N. M. Chem. Rev. 2003, 103, 4593
30. The best experimental rate constant for a reference reaction (2-allylbenzyl radical abstracting hydrogen from meta -xylene; Franz, J. A.; Alnajjar, M. S.; Barrows, R. D.; Kaisaki, D. L.; Camaioni, D. M.; Suleman, N. K. J. Org. Chem. 1986, 51, 1446) has an error of 0.7 kcal/mol in the activation energy and 0.4 in log A. The group additivity parameters (from Benson's book, ref 58 in ref 13) have errors associated with them as well. An overall estimate of the errors in the experimental values is 1-2 kcal/mol for the activation energies and 2.5 for ln A.
31. Hou, Z.; Bennett, C. A.; Klein, M. T.; Virk, P. S. Energy Fuels 2010, 24, 58