Kinetics and thermochemistry for the gas-phase keto-enol tautomerism of phenol ↔ 2,4-cyclohexadienone

Journal of Physical Chemistry A

Volumn 107, Issue 19, 2003, Pages 3696-3703

  Zhu, Li ^a   Bozzelli, Joseph W ^a  

^a NEW JERSEY INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXADIENONE; GAS PHASE KETO ENOL TAUTOMERISM; IDEAL GAS THERMOCHEMICAL PROPERTIES; ISODESMIC REACTIONS; TAUTOMERIZATION; THERMOCHEMISTRY;

CALCULATIONS; CARBON; CHEMICAL BONDS; DECOMPOSITION; ISOMERIZATION; RATE CONSTANTS; REACTION KINETICS; THERMODYNAMIC PROPERTIES;

PHENOLS;

EID: 0038010550     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0212545     Document Type: Article

References (53)

1. Born, J. G. P.; Louw, R.; Mulder, P. Chemosphere 1989, 19, 401.
2. Wiater, I.; Born, J. G.; Louw, R. Eur. J. Org. Chem. 2000, 6, 921.
3. Parker, J. K.; Davis, S. R. J. Am. Chem. Soc. 1999, 121, 4271.
4. Hodgson, D.; Zhang, H.; Nimlos, M. R.; McKinnon, J. T. J. Phys. Chem. A 2001, 105, 4316.
5. Lovell, A. B.; Brezinsky, K.; Glassman, I. Int. J. Chem. Kinet. 1989, 21, 547.
6. Manion, J. A.; Louw, R. J. Phys. Chem. 1989, 93, 3563.
7. Horn, C. Roy, K.: Frank, P.; Just, T. "Shock-Tube Study on the High-Temperature Pyrolysis of Phenol"; 27th Symposium (International) on Combustion, University of Colorado at Boulder, 1998.
8. Cypres, R.; Bettens, B. Tetrahedron 1974, 30, 1253.
9. Le, H. T.; Flammang, R.; Gerbaux, P.; Bouchoux, G.; Nguyen, M. T. J. Phys. Chem. A 2001, 105, 11582.
10. Perez, P.; Toro-Labbe, A. J. Phys. Chem. A 2000, 104, 1557.
11. Smith, B. J.; Nguyen, M. T.; Bouma, W. J. Am. Chem. Soc. 1991, 113, 6452.
12. Krsge, A. J. Chemtracts-Org. Chem. 2002, 15, 212.
13. Capponi, M.; Gut, I. G.; Hellrung, B.; Persy, G.; Wirz, J. Can. J. Chem. 1999, 77, 605.
14. Wiater, I.; Louw, R. Organohalogen Compounds 1999, 41, 77.
15. Capponi, M.; Gut, I. W. J. Angew. Chem., Int. Ed. Engl. 1986, 25, 344.
16. Tee, O. S.; Inyengar, N. R. J. Am. Chem. Soc. 1985, 107, 455.
17. Shiner, C. S.; Vorndam, P. E.; Kass, S. R. J. Am. Chem. Soc. 1986, 108, 5699.
18. Gadosy, T. A.; McClelland, R. A. J. Mol. Struct. (THEOCHEM) 1996, 369, 1.
19. Santoro, D.; Louw, R. J. Chem. Soc., Perkin Trans. 2 2001, 4, 645.
20. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822.
21. 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.; 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.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
22. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 2000, 112, 6532.
23. Hehre, W.; Radom, L.; Schleyer, P. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley & Sons: New York, 1986.
24. Redfern, P. C.; Zapol, P.; Curtiss, L. A.; Raghavachari, K. J. Phys. Chem. A 2000, 104, 5850.
25. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Stefanov, B. B. J. Chem. Phys. 1998, 108, 692.
26. Raghavachari, K.; Stefanov, B. B.; Curtiss, L. A. J. Chem. Phys. 1997, 106, 6764.
27. Zhu, L.; Chen, C.; Bozzelli, J. W. J. Phys. Chem. A 2000, 104, 9197.
28. Sheng, C. Ph.D. Dissertation, Department of Chemical Engineering, New Jersey Institute of Technology, 2002.
29. Shokhirev, N. V. http://www.chem.arizona.edu/faculty/walk/nikolai/programs.html#programs
30. Lay, T. H.; Krasnoperov, L. N.; Venanzi, C. A.; Bozzelli, J. W. J. Phys. Chem. 1996, 100, 8240.
31. Zhu, L.; Bozzelli, J. W. J. Phys. Chem. A 2002, 106, 345.
32. Sun, H.; Chen, C.; Bozzelli, J. W. J. Phys. Chem. A 2000, 104, 8270.
33. Sun, H.; Bozzelli, J. W. J. Phys. Chem. A 2001, 105, 4504.
34. Sun, H.; Bozzelli, J. W. J. Phys. Chem. A 2001, 105, 9543.
35. Sun, H.; Bozzelli, J. W. J. Phys. Chem. A 2002, 106, 3947.
36. Jung, D.; Chen, C.; Bozzelli, J. W. J. Phys. Chem. A 2000, 104, 9581.
37. Jung, D.; Bozzelli, J. W. J. Phys. Chem. A 2001, 105, 5420.
38. Chen, C.; Lay, T. H.; Bozzelli, J. W. J. Phys. Chem. A 2003, submitted.
39. Marsh, K. N.; Wilhoit, R. C.; Frenkel, M.; Yin, D. Thermodynamic Properties of the Substances in Ideal Gas State: Linear and Nonlinear Function Coefficients Data Files and Computer Codes to Regenerate the Values of Thermodynamic Properties, Version 1.0M, Thermodynamics Research Center (TRC), The Texas Engineering Experiment Station (TEES), Texas A&M University System, College Station, TX 77843, 1994. Currently at U.S. National Institute of Standards and Technology, Boulder, CO.
40. Benson, S. W. Thermochemical Kinetics; Wiley-Interscience: New York, 1976.
41. Zhu, L.; Bozzelli, J. W. Chem. Phys. Lett. 2002, 357, 65.
42. He, Y. Z.; Mallard, W. G.; Tsang, W. J. Phys. Chem. 1988, 92, 2196.
43. Ritter, E. R. J. Chem. Inf. Comput. Sci. 1991, 31, 400.
44. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
45. Pedley, J. B.; Naylor, R. O.; Kirby, S. P. Thermodynamic Data of Organic Compounds, 2nd ed.; Chapman and Hall: London, 1986.
46. Guthrie, J. P. Can. J. Chem. 1978, 56, 962.
47. Melius, C. http://z.ca.sandia.gov/~melius/; Unpublished data.
48. Allinger, N. L.; Dodziuk, H.; Rogers, D. W.; Naik, S. N. Tetrahedron 1982, 38, 1593.
49. Furuyama, S.; Golden, D. M.; Benson, S. W. J. Chem. Thermodyn. 1970, 2, 161.
50. Karni, M.; Oref, I.; Burcat, A. J. Phys. Chem. Ref. Data 1991, 20, 665.
51. Wang, H.; Brezinsky, K. J. Phys. Chem. A 1998, 102, 1530.
52. Wiberg, K. B.; Crocker, L. S.; Morgan, K. M. J. Am. Chem. Soc. 1991, 113, 3447.
53. Kabo, G. J.; Yursha, I. A.; Frenkel, M. L.; Poleshchuk, P. A.; Fedoseenko, V. I.; Ladutko, A. I. J. Chem. Thermodyn. 1988, 20, 429.