Reaction Paths of Keto-Enol Tautomerization of β-Diketones

Journal of Physical Chemistry A

Volumn 108, Issue 14, 2004, Pages 2750-2757

  Yamabe, Shinichi ^a   Tsuchida, Noriko ^a   Miyajima, Kenta ^a  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; ALDEHYDES; APPROXIMATION THEORY; CARBOXYLIC ACIDS; CATALYSTS; COMPUTATIONAL METHODS; FREQUENCIES; HYDROGEN BONDS; OPTIMIZATION; PROBABILITY DENSITY FUNCTION; PROTONS; SOLVENTS;

ACETYLACETONE; DENSITY FUNCTIONAL THEORY (DFT); EQUILIBRIUM SHIFTS; TAUTOMERIZATION;

KETONES;

EID: 84962467339     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp031243r     Document Type: Article

References (56)

1. Emsley, J. Struct. Bonding. (Berlin) 1984, 57, 147.
2. Fowling, J.; Bernstein, H. J. J. Am. Chem. Soc. 1951, 73, 4353.
3. (b) Spencer, J. N.; Holmboe, E. S.; Kirshenbaum, M. R.; Firth, D. W.; Pinto, P. B. Can. J. Chem. 1982, 60, 1178.
4. (c) Emsley, J.; Freeman, N. J. J. Mol. Struct. 1987, 161, 193.
5. (d) Rogers, M. T.; Burdett, J. L. Can. J. Chem. 1965, 43, 1516.
6. (e) Wallen, S. L.; Yonker, C. R.; Phelps, C. L.; Wai, C. M. J. Chem. Soc., Faraday Trans. 1997, 93, 2391.
7. (f) Blokzijl, W.; Engberts, J. B. F. N.; Blandamer, M. J. J. Chem. Soc., Perkin Trans II 1994, 455.
8. (g) Iglesias, E. J. Chem. Soc., Perkin Trans II 1997, 431.
9. (h) Folkendt, M. M.; Weiss-Lopez, B. E.; Chauvel, J. P., Jr.; True, N. S. J. Phys. Chem. 1985, 89, 3347.
10. Iijima, K.; Ohnogi, A.; Shibata, S. J. Mol. Struct. 1987, 156, 111.
11. (b) Lowrey, A. H.; George, C.; D'Antonio, P.; Karle, J. J. Am. Chem. Soc. 1971, 93, 6399.
12. Adamo, C.; Barone, V. Chem. Phys. Lett. 1997, 274, 242.
13. (b) Smedarchina, Z.; Siebrand, W.; Zgierski, M. Z. J. Chem. Phys. 1995, 103, 5326.
14. (c) Luth, K.; Soheiner, S. Int. J. Quantum Chem. Symp. 1993, 27, 419.
15. (d) Chiavassa, T.; Verlaque, P.; Pizzala, L.; Allouche, A.; Roubin, P. J. Phys. Chem. 1993, 97, 5917.
16. (e) Tuppurainen, K.; Laatikainen, R. THEOCHEM 1993, 100, 15.
17. (f) Bosch, E.; Moreno, M.; Lluch, J. M. J. Am. Chem. Soc. 1992, 114, 2072.
18. (g) Wiberg, K. B.; Hadad, C. M.; Lepage, T. J.; Breneman, C. M.; Frisch, M. J. J. Phys. Chem. 1992, 96, 671.
19. (h) Latajka, Z.; Scheiner, S. J. Chem. Phys. 1992, 96, 9764.
20. (i) Chiavassa, T.; Roubin, P. Pizzala, L.; Verlaque, P.; Allouche, A.; Marinelli, F. J. Phys. Chem. 1992, 96, 10659.
21. (j) Rios, M. A.; Rodriguez, J. THEOCHEM 1991, 74, 149.
22. (k) Craw, J. S.; Nascimento, M. A. C. Chem. Phys. Lett. 1990, 168, 423.
23. (l) Bosch, E.; Moreno, M.; Lluch, J. M.; Bertran, J. J. Chem. Phys. 1990, 93, 5685.
24. (m) Shida, N.; Barbara, P. F.; Almlöf, J. E. J. Chem. Phys. 1989, 91, 4061.
25. (n) Binkley, J. S.; Frisch, M. J.; Schaefer, H. F. Chem. Phys. Lett. 1986, 126, 1.
26. (o) Kral, V.; Laatikainen, R.; Arnold, Z. Tetrahedron 1985, 41, 4919.
27. (p) Frisch, M. J.; Scheiner, A. C.; Schaefer, H. F.; Binkley, J. S. J. Chem. Phys. 1985, 82, 4194.
28. (q) Bonaccorsi, R.; Ghio, C.; Tomasi, J. Int. J. Quantum Chem. 1984, 26, 637.
29. (r) Bicerano, J.; Schaefer, H. F.; Miller, W. H. J. Am. Chem. Soc. 1983, 105, 2550.
30. (s) Fluder, E. M.; De La Vega, J. R. J. Am. Chem. Soc. 1978, 100, 5265.
31. (t) Catalan, J.; Yanez, M.; Fernandez-Alons, J. I. J. Am. Chem. Soc. 1978, 700, 6917.
32. Rios, M. A.; Rodriguez, J. THEOCHEM 1990, 63, 137.
33. (b) Dannenberg, J. J.; Rios, R. J. Phys. Chem. 1994, 98, 6714.
34. Ishida, T.; Hirata, F.; Kato, S. J. Chem. Phys. 1999, 770, 3938.
35. Bach, R. D.; Canepa, C. J. Org. Chem. 1996, 61, 6346.
36. (b) Tarakeshwar, P.; Manogaran, S. THEOCHEM 1996, 362, 77.
37. (c) Deerfield, D. W.; Pedersen, L. G. THEOCHEM 1996, 368, 163.
38. (d) Yliniemela, A.; Uchimaru, T.; Hirose, T.; Baldwin, B. W.; Tanabe, K. THEOCHEM 1996, 369, 9.
39. (e) Han, S. J.; Kim, Y. J.; Kang, Y. K. THEOCHEM 1996, 369, 145.
40. (f) Kutzler, F. W.; White, C. T.; Cook, M. Chem. Phys. Lett. 1988, 147, 263.
41. (g) Merchan, M.; Tomas, F.; Nebot-Gil, I. THEOCHEM 1984, 709, 51.
42. (h) Fitzpatrick, N. J.; Sayal, P.; Al-Obadie, M. S.; Katrib, A. J. Mol. Struct. 1982, 87, 129.
43. Present results of (U)B3LYP/6-311+G(2d,p) calculations.
44. Yamabe, S.; Tsuchida, N. J. Comput. Chem. 2003, 24, 939.
45. (b) Yamabe, S.; Tsuchida, N. Internet Electronic. J. Mol. Design. 2003, 2, 1.
46. Lee, D.; Kim, C. K.; Lee, B.-S.; Lee, I.; Lee, B. C. J. Compt. Chem. 1997, 18, 56.
47. (b) Field, M. J.; Killer, I. H. J. Chem. Soc., Perkin Trans II 1987, 617.
48. Hecke, A. D. J. Chem. Phys. 1993, 98, 5648.
49. Onsager, L. J. Am. Chem. Soc. 1938, 58, 1486.
50. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
51. Fukui, J. Phys. Chem. 1970, 74, 4161.
52. (b) Gonzalez, C.; Schleger, H. B. J. Phys. 1987, 90, 2154.
53. 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.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
54. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
55. In the gas phase, the keto B form is 0.79 kcal/mol (B3LYP/6311+G(2d,p)) more stable than the keto A form. On the other hand, when two water molecules are coordinated to the malonic acid molecule, keto A is 3.93 kcal/mol more stable. In order to shows that the keto A is a reactant, two water molecules (024H25H26 and 027H28H29) were added.
56. Banthorpe, D. V. Reaction Mechanism in Organic Chemistry, Vol. 2: Elimination Reactions; Hughes, E. D., Ed.; Elsevier: London, 1963.