Activation energies of pericyclic reactions: Performance of DFT, MP2, and CBS-QB3 methods for the prediction of activation barriers and reaction energetics of 1,3-dipolar cycloadditions, and revised activation enthalpies for a standard set of hydrocarbon pericyclic reactions

Journal of Physical Chemistry A

Volumn 109, Issue 42, 2005, Pages 9542-9553

  Ess, Daniel H ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; DENSITY FUNCTIONAL METHODS; PERICYCLIC REACTIONS; REACTION ENERGETICS;

ACTIVATION ENERGY; ADDITION REACTIONS; ERROR ANALYSIS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

HYDROCARBONS;

EID: 27744489233     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp052504v     Document Type: Article

References (84)

1. Quantum-Mechanical Prediction of Thermochemical Data; Cioslowski, J., Ed.; Kluwer Academic Publishers: Boston, MA, 2001; Vol. 22, pp 1-245.
2. Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. J. Chem. Phys. 1989, 90, 5622-5629.
3. Curtiss, L. A.; Jones, C.; Trucks, G. W.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1990, 93, 2537-2545.
4. Curtiss, L. A.; Trucks, G. W.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221-7230.
5. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764-7776.
6. Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822-2827.
7. Nyden, M. R.; Petersson, G. A. J. Chem. Phys. 1981, 75, 1843-1862.
8. Al-Laham, M. A.; Petersson, G. A. J. Chem. Phys. 1991, 94, 6081-6090.
9. Petersson, G. A.; Tensfeldt, T. G.; Montgomery, J. A. J. Chem. Phys. 1991, 94, 6091-6101.
10. Petersson, G. A.; Malick, D. K.; Wilson, W. G.; Ochterski, J. W.; Montgomery, J. A.; Frisch, M. J. J. Chem. Phys. 1998, 109, 10570-10579.
11. Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 2000, 112, 6532-6542.
12. Martin, J. M. L.; Oliveria, G. J. Chem. Phys. 1999, 111, 1843-1856.
13. Recent Advances in Density Functional Methods; Chong, D. P., Ed.; World Scientific: Singapore, 1997; Parts I and II.
14. Recent Advances in Density Functional Methods; Barone, V., Bencini, A., Eds.; World Scientific: Singapore, 1999; Part III.
15. Adamo, C.; di Matteo, A.; Barone, V. Adv. Quantum Chem. 1999, 36, 45-76.
16. Guner, V.; Khuong, K. S.; Leach, A. G.; Lee, P. S.; Bartberger, M. D.; Houk, K. N. J. Phys. Chem. A 2003, 107, 11445-11459.
17. Guner, V. A.; Khuong, K. S.; Houk, K. N.; Chuma, A.; Pulay, P. J. Phys. Chem. A 2004, 108, 2959-2965.
18. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
19. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
20. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265-3269.
21. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301.
22. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565-598.
23. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633-645.
24. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1968, 7, 321-328.
25. Huisgen, R. J. Org. Chem. 1968, 33, 2291-2297.
26. Huisgen, R. J. Org. Chem. 1976, 41, 403-419.
27. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 1.
28. Houk, K. N. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 2.
29. Houk, K. N. J. Am. Chem. Soc. 1972, 94, 8953-8955.
30. Caramella, P.; Gandour, R. W.; Hall, J. A.; Deville, C. G.; Houk, K. N. J. Am. Chem. Soc. 1977, 99, 385-392.
31. Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1976, 98, 6397-6399.
32. Houk, K.N.; Sims, J. J. Am. Chem. Soc. 1973, 95, 5798-5800.
33. Houk, K. N.; Sims, J.; Duke, R. E., Jr.; Strozier, R. W.; George, J. K. J. Am. Chem. Soc. 1973, 95, 7287-7301.
34. Houk, K. N.; Sims, J.; Watts, C. R.; Luskus, L. J. J. Am. Chem. Soc. 1973, 95, 7301-7315.
35. Houk, K. N. Acc. Chem. Res. 1975, 8, 361-369.
36. Poppinger, D. J. Am. Chem. Soc. 1975, 97, 7486-7488.
37. Caramella, P.; Houk, K. N.; Domelsmith, L. N. J. Am. Chem. Soc. 1977, 99, 4511-4514.
38. Dewar, M. J. S.; Olivella, S.; Rzepa, H. S. J. Am. Chem. Soc. 1973, 100, 5650-5659.
39. Su, M.; Liao, H.; Chung, W.; Chu, S. J. Org. Chem. 1999, 64, 6710-6716.
40. Confalone, P. N.; Huie, E. M. Org. React. (N.Y.) 1988, 36, 1.
41. Sustmann, R.; Wenning, E. Tetrahedron Lett. 1977, 10, 877-880.
42. Sustmann, R. Tetrahedron Lett. 1971, 12, 2717-2720.
43. Goddard, W. A., III; Dunning, T. H., Jr.; Hunt, W. J.; Hay, P. J. Acc. Chem. Res. 1973, 6, 368-376.
44. Yamaguchi, K.; Nishio, A.; Yabushita, S.; Fueno, T. Chem. Phys. Lett. 1978, 53, 109-114.
45. Yamaguchi, K.; Yabushita, S.; Fueno, T.; Kato, S.; Morokuma, K.; Iwata, S. Chem. Phys. Lett. 1980, 71, 563-568.
46. Hiberty, P. C.; Ohanessian, G. J. Am. Chem. Soc. 1982, 104, 66-70.
47. Firestone, R. A. J. Org. Chem. 1968, 33, 2285-2290.
48. Firestone, R. A. J. Org. Chem. 1968, 37, 2181-2191.
49. Firestone, R. A. Tetrahedron 1977, 33, 3009-3039.
50. Hiberty, P. C.; Ohanessian, G.; Schlegel, H. B. J. Am. Chem. Soc. 1983, 105, 719-723.
51. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133-A1138.
52. Hohenberg, P.; Kohn, W. Phys. Rev. 1965, 136, B864-B871.
53. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
54. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Chem. Phys. 1994, 98, 11623-11627.
55. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675.
56. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811-4815.
57. Lynch, B. J.; Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2003, 107, 1384-1388.
58. Lynch, B. J.; Truhlar, D. G. J. Phys. Chem. A 2001, 105, 2936-2941.
59. Lynch, B. J.; Truhlar, D. G. J. Phys. Chem. A 2002, 106, 842-846.
60. Lynch, B. J.; Truhlar, D. G. J. Phys. Chem. A 2003, 107, 3898-3906.
61. Frisch, M. J.; et al. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
62. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
63. Geittner, J.; Huisgen, R.; Reissig, H. U. Heterocycles 1978, 109.
64. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
65. Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503-506.
66. Boese, A. D.; Martin, J. M. L. J. Chem. Phys. 2004, 121, 3405-3416.
67. Sancho-Garcia, J. C.; Corrnil, J. J. Chem. Phys. 2004, 121, 3096-3101.
68. Gherman, B. F.; Lippard, S. J.; Friesner, R. A. J. Am. Chem. Soc. 2005, 127, 1025-1037.
69. Alajarin, M.; Sanchez-Andrada, P.; Vidal, A.; Tovar, F. J. Org. Chem. 2005, 70, 1340-1349.
70. Goumans, T. P. M.; Ehlers, A. W.; Lammertsma, K.; Wuerthwein, E.-U.; Grimme, S. Chem.-Eur. J. 2004, 10, 6468-6475.
71. Hauser, W. P.; Walters, W. D. J. Phys. Chem. 1968, 67, 1328-1333.
72. Lewis, K. E.; Steiner, H. J. Chem. Soc. 1964, 3080.
73. Roth, W. R.; Biermann, M.; Dekker, H.; Jochems, R.; Mosselman, C.; Herman, H. Chem. Ber. 1978, 111, 3892-3903.
74. Roth, W. R. Chimia 1966, 229, 20.
75. Roth, W. R. Tetrahedron Lett. 1964, 1009-1013.
76. Doering, W. E.; Toscano, V. G.; Beasley, G. H. Tetrahedron 1971, 27, 5299-5306.
77. Rowley, D.; Steiner, H. Discuss. Faraday Soc. 1951, 27, 5299-5306.
78. Walls, R.; Wells, J. M. J. Chem. Soc., Perkin Trans. 2 1976, 52-55.
79. Benford, G. A.; Wassermann, A. J. Chem. Soc. 1939, 362, 367-371.
80. Turnbull, A. G.; Hull, H. S. Aust. J. Chem. 1968, 21, 1789-1797.
81. Herndon, W. C.; Grayson, C. R.; Manion, J. M. J. Org. Chem. 1967, 32, 526-529.
82. Spielman, W.; Fick, H. H.; Meyer, L. U.; de Meijere, A. Tetrahedron Lett. 1976, 45, 4057.
83. Maas, M.; Lutterbeck, M.; Hunkler, D.; Prinzbach, H. Tetrahedron Lett. 1983, 24, 2143-2149.
84. Mohler, D. L.; Vollhardt, R. P. C.; Wolf, S. Angew. Chem., Int. Ed. Engl. 1990, 29, 1151-1154.