Photostability via a sloped conical intersection: A CASSCF and RASSCF study of pyracylene

Journal of Physical Chemistry A

Volumn 109, Issue 39, 2005, Pages 8849-8856

  Boggio Pasqua, Martial ^a   Robb, Michael A ^a   Bearpark, Michael J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

RELIABILITY; STABILITY; SURFACE CHEMISTRY;

ENERGY SURFACES; PHOTOSTABILITY; PYRACYLENE; SLOPED CONICAL INTERSECTION;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 26844465102     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp053354r     Document Type: Article

References (71)

1. Freiermuth, B.; Gerber, S.; Riesen, A.; Wirz, J.; Zehnder, M. J. Am. Chem. Soc. 1990, 112, 738.
2. Roos, B. O. Adv. Chem. Phys. 1987, 69, 399.
3. Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1992, 114, 1606.
4. Bearpark, M. J.; Robb, M. A.; Bernardi, F.; Olivucci, M. Chem. Phys. Lett. 1994, 217, 513.
5. Crittenden, B. D.; Long, R. Environ. Sci. Technol. 1973, 7, 742.
6. Schultz, J. L.; Kessler, T.; Friedel, R. A.; Sharkey, A. G. Fuel 1972, 51, 242.
7. (a) Laflamme, R. E.; Hites, R. A. Geochim. Cosmochim. Acta 1978, 42, 289.
8. (b) Lee, M. L.; Prado, G. P.; Howard, J. B.; Hites, R. A. Biomed. Mass Spectrom. 1977, 4, 182.
9. (c) Howard, J. B.; Longwell, J. P. In Polynuclear Aromatic Hydrocarbons: Formation, Metabolism, and Measurement; Cooke, M., Dennis, A. J., Eds.; Battelle Press: Columbus, OH, 1983; p 27.
10. Keller, R. In Polycyclic Aromatic Hydrocarbons and Astrophysics; Léger, A., et al., Eds.; Reidel: Dordrecht, The Netherlands, 1987; p 387.
11. (a) Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162.
12. (b) Zhang, Q. L.; O'Brien, S. C.; Heath, J. R.; Liu, Y.; Curl, R. F.; Kroto, H. W.; Smalley, R. E. J. Phys. Chem. 1986, 90, 525.
13. (c) Yang, S. H.; Pettiette, C. L.; Chesnovsky, O.; Smalley, R. E. Chem. Phys. Lett. 1987, 139, 233.
14. (d) Heath, J. R.; Curl, R. F.; Smalley, R. E. J. Chem. Phys. 1987, 87, 4236.
15. (e) Kroto, H. Science 1988, 242, 1139.
16. (f) Aihara, J.; Hosoya, H. Bull. Chem. Soc. Jpn. 1988, 61, 2657.
17. (g) Mallion, R. B. Nature 1987, 325, 760.
18. Nunzi, F.; Sgamellotti, A.; Re, N. J. Chem. Soc., Dalton Trans. 2002, 3, 399 and references therein.
19. Poater, J.; Solà, M.; Viglione, R. G.; Zanasi, R. J. Org. Chem. 2004, 69, 7537-7542, and references therein.
20. Diogo, H. P.; Kiyobayashi, T.; Minas da Piedade, M. E.; Burlak, N.; Rogers, D. W.; McMasters, D.; Persy, G.; Wirz, J.; Liebman, J. F. J. Am. Chem. Soc. 2002, 124, 2065-2072.
21. (a) Trost, B. M.; Bright, G. M. J. Am. Chem. Soc. 1967, 89, 4244.
22. (b) Trost, B. M.; Nelsen, S. F.; Britelli, D. R. Tetrahedron Lett. 1967, 40, 3959.
23. (c) Trost, B. M.; Bright, G. M. J. Am. Chem. Soc. 1968, 90, 2732.
24. (d) Trost, B. M.; Bright, G. M. J. Am. Chem. Soc. 1969, 91, 3689.
25. (e) Trost, B. M.; Bright, G. M.; Frihart, C.; Britelli, D. J. Am. Chem. Soc. 1971, 93, 737.
26. (f) Trost, B. M. In Topics in Nonbenzenoid Aromatic Chemistry; Hirokawa Publishing Co.: Tokyo, 1973; Vol. I, p 243.
27. (g) Trost, B. M.; Buhner, D.; Bright, G. M. Tetrahedron Lett. 1973, 29, 2787.
28. (h) Trost, B. M.; Herdle, W. B. J. Am. Chem. Soc. 1976, 98, 4080.
29. Aihara, J. Bull. Chem. Soc. Jpn. 1988, 61, 1451.
30. Stein, S. E.; Fahr, A. J. Phys. Chem. 1985, 89, 3714.
31. Bearpark, M. J.; Boggio-Pasqua, M.; Robb, M. A.; Ogliaro, F. Accepted for publication in Theor. Chem. Acc.
32. Atchity, G. J.; Xantheas, S. S.; Ruedenberg, K. J. Chem. Phys. 1991, 95, 1862.
33. Migani, A.; Olivucci, M. In Conical Intersections: Electronic Stucture, Dynamics and Spectroscopy; Domcke, W., Yarkony, D. R., Koppel, H., Eds.; Advanced Series in Physical Chemistry 15; World Scientific: Singapore, 2004; p 271.
34. Paterson, M. J.; Robb, M. A.; Blancafort, L.; DeBellis, A. D. J. Am. Chem. Soc. 2004, 126, 2912.
35. De Vico, L.; Page, C. S.; Garavelli, M.; Bernardi, F.; Basosi, R.; Olivucci, M. J. Am. Chem. Soc. 2002, 124, 4124.
36. Ben-Nun, M.; Molnar, F.; Schulten, K.; Martínez, T. J. Proc. Natl. Acad. Sci. 2002, 99, 1769.
37. Yarkony, D. R. J. Chem. Phys. 2001, 114, 2601.
38. (a) Bearpark, M. J.; Bernardi, F.; Clifford, S.; Olivucci, M.; Robb, M. A.; Smith, B. R.; Vreven, T. J. Am. Chem. Soc. 1996, 118, 169.
39. (b) Bearpark, M. J.; Celani, P.; Jolibois, F.; Olivucci, M.; Robb, M. A.; Bernardi, F. Mol. Phys. 1999, 96, 645.
40. (c) Boggio-Pasqua, M.; Ravaglia, M.; Bearpark, M. J.; Garavelli, M.; Robb, M. A. J. Phys. Chem. A 2003, 107, 11139.
41. Bearpark, M. J.; Boggio-Pasqua, M. Theor. Chem. Acc. 2003, 110, 105.
42. (a) Olsen, J.; Roos, B. O.; Jørgensen, P.; Jensen, H. J. A. J. Chem. Phys. 1988, 89, 2185.
43. (b) Malmqvist, P. A.; Rendell, A.; Roos, B. O. J. Phys. Chem. 1990, 94, 5477.
44. This contrasts with our use of RASSCF to extend a CASSCF active space and recover dynamic correlation for ionic states (see ref 29). However, both contrasting approaches rely on using RASSCF with a small subset of the full CASSCF configuration list for a particular orbital active space.
45. (a) Ditchfield, R.; Herhe, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
46. (b) Herhe, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
47. (c) Harihan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
48. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007.
49. Boggio-Pasqua, M.; Bearpark, M. J.; Klene, M.; Robb, M. A. J. Chem. Phys. 2004, 120, 7849.
50. (a) Werner, H.-J.; Knowles, P. J. J. Chem. Phys. 1988, 89, 5803.
51. (b) Knowles, P. J.; Werner, H.-J. Chem. Phys. Lett. 1988, 145, 514.
52. Bito, Y.; Shida, N.; Toru, T. Chem. Phys. Lett. 2000, 328, 310.
53. Celani, P.; Werner, H.-J. J. Chem. Phys. 2000, 112, 5546.
54. (a) Hashimoto, T.; Nakano, H.; Hirao, K. J. Chem. Phys. 1996, 104, 6244.
55. (b) Rubio, M.; Merchán, M.; Ortí, E.; Roos, B. O. Chem. Phys. 1994, 179, 395.
56. González-Luque, R.; Serrano-Andrés, L.; Merchán, M.; Fülscher, M. P. Theor. Chem. Acc. 2003, 110, 224.
57. Kawashima, Y.; Hashimoto, T.; Nakano, H.; Hirao, K. Theor. Chem. Acc. 1999, 102, 49.
58. Blancafort, L.; Celani, P.; Bearpark, M. J.; Robb, M. A. Theor. Chem. Acc. 2003, 110, 92.
59. McWeeny, R.; Sutcliffe, B. T. In Molecular Quantum Mechanics; Academic Press: New York, 1969; pp 148-170.
60. Werner, H.-J.; et al. MOLPRO, version 2002.6; Birmingham, UK, 2003.
61. Frisch, M. J.; et al. Gaussian Development Version, revision B.07; Gaussian, Inc.: Pittsburgh, PA, 2003.
62. Atchity, G. J.; Xantheas, S. S.; Ruedenberg, K. J. Chem. Phys. 1991, 95, 1862-1876.
63. Maksic, Z. B.; Baric, D.; Petanjek, I. J. Phys. Chem. A 2000, 104, 10873-10881.
64. Cave, R. J. In Modern Electronic Structure Theory And Applications In Organic Chemistry; Davidson, E. R.; Ed.; World: Singapore, 1997; p 239.
65. (a) Serrano-Andrés, L.; Merchán, M.; Nebot-Gil, I.; Lindh, R.; Roos, B. O. J. Chem. Phys. 1993, 98, 3151.
66. (b) Cave, R. J.; Davidson, E. R. J. Chem. Phys. 1988, 92, 614.
67. (c) Cave, R. J.; Davidson, E. R. Chem. Phys. Lett. 1988, 148, 190.
68. Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1992, 114, 1606.
69. Bearpark, M. J.; Robb, M. A.; Bernardi, F.; Olivucci, M. Chem. Phys. Lett. 1994, 277, 513.
70. Bearpark, M. J.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Phys. Chem. A 1997, 101, 8395.
71. Celani, P.; Ottani, S.; Olivucci, M.; Bernardi, F.; Robb, M. A. J. Am. Chem. Soc. 1994, 116, 10141.