The C5H6NH2+ protonated Shiff base: An ab initio minimal model for retinal photoisomerization

Journal of the American Chemical Society

Volumn 119, Issue 29, 1997, Pages 6891-6901

  Garavelli, M ^a   Celani, P ^b   Bernardi, F ^a   Robb, M A ^b   Olivucci, M ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

RETINAL;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; ISOMERISM; MODEL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0030794947     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9610895     Document Type: Article

References (59)

1. Yoshizawa, T.; Kuwata, O. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Ed.; CRC Press: Boca Raton, FL, 1995; pp 1493-1499.
2. (a) Schoenlein, R. W.; Peteanu, L. A.; Mathies, R. A.; Shank C. V. Science 1991, 254, 412-415.
3. (b) Wang, Q.; Schoenlein, R. W.; Peteanu, L. A.; Mathies, R. A.; Shank, C. V. Science 1994, 266, 422-424.
4. (a) Kandori, H.; Sasabe, H.; Nakanishi, K.; Yoshizawa, T.; Mizukami, T.; Shichida, Y. J. Am. Chem. Soc. 1996, 118, 1002, 1005.
5. (b) Mizukami, T.; Kandori, H.; Shichida, Y.; Chen, A.-H.; Derguini, F.; Caldwell, C. G.; Bigge, C. Y.; Nakanishi, K.; Yoshizawa, T. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 4072-4076.
6. Kandori, H.; Katsuta, Y.; Ito, M.; Sasabe, H. J. Am. Chem. Soc. 1995, 117, 2669-2670.
7. Logunov, S. L.; Song, L.; El-Sayed, M. J. Phys. Chem. 1996, 100, 18586-18591.
8. Hamm, P.; Zurek, M.; Röschinger, T.; Patzelt, H.; Oesterhelt, D.; Zinth, W. Chem. Phys. Lett. 1996, 263, 613-621.
9. Delaney, J. K.; Brack, T. L.; Atkinson, G. H.; Ottolenghi, M.; Steinberg, G.; Sheves, M. Proc. Natl. Acad. Sci. U.S.A. 1995, 90, 2101-2105.
10. Haran, G.; Wynne, K.; Xie, A.; He, Q.; Chance, M.; Hochstasser, R. M. Chem. Phys. Lett. 1996, 389-395.
11. Serrano-Andrés, L.; Lindh, R.; Roos, B. O.; Merchán, M. J. Phys. Chem. 1993, 97, 9360-9368.
12. Celani, P.; Garavelli, M.; Ottani, S.; Bernardi, F.; Robb, M. A.; Olivucci, M. J. Am. Chem. Soc. 1995, 117, 11584-11585.
13. (a) Roos, B. O. Adv. Chem. Phys. 1987, 69, 399-446.
14. (b) The MC-SCF program used is implemented in the following: Gaussian 94, Revision B.2; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
15. (a) Andersson, K.; Malmqvist, P.-A.; Ross, B. O. J. Chem. Phys. 1992, 96, 1218.
16. (b) MOLCAS, Version 3; Andersson, K.; Blomberg, M. R. A.; Fülscher, M.; Kellö, V.; Lindh, R.; Malmqvist, P.-A.; Noga, J.; Olsen, J.; Roos, B. O.; Sadlej, A. J.; Siegbahn, P. E. M.; Urban, M.; Widmark, P. O.; University of Lund, Sweden, 1994.
17. Freedman, K. A.; Becker, R. S. J. Am. Chem. Soc. 1986, 108, 1245-1251.
18. There is no general agreement on the value of this twisting angle of the 11-cis-retinal chromophore. In this molecule, the β-ionone ring is assumed to be 6-s-cis. For this conformation, Sakurai et al. (Sakurai, M.; Wada, M.; Inoue, Y.; Tamura, Y.; Watanabe, Y. J. Phys. Chem. 1996, 100, 1957-1964) give a value of 59°. Davidson et al. take a value of 57-58° (see ref 15). An estimate based upon a partial b31yp/6-31-G* geometry optimization gives a 30° angle.
19. Du, P.; Davidson, E. R. J. Phys. Chem. 1990, 94, 7013-7020.
20. Du, P.; Racine, C.; Davidson, E. R. J. Phys. Chem. 1990, 94, 3944-3951.
21. (a) Martin, C. H. J. Phys. Chem. 1996, 100, 14310-14315.
22. (b) Martin, C. H. Chem. Phys. Lett. 1996, 257, 229-237.
23. (a) Bonacic-Koutecky, V.; Köhler, J.; Michl, J. Chem. Phys. Lett. 1984, 104, 440-443.
24. (b) Bonacic-Koutecky, V.; Schöffel, K.; Michl, J. Theor. Chim. Acta 1987, 72, 459-474.
25. Dobado, J. A.; Nonella, M. J. Phys. Chem. 1996, 100, 18282-18288.
26. Dormans, G. J.; Groenenboom, G. C.; van Dorst, W. C. A.; Buck, H. M. J. Am. Chem. Soc. 1988, 110, 1406-1415.
27. (a) Weiss, R. M.; Warshel, A. J. Am. Chem. Soc. 1979, 101, 6131-6133.
28. (b) Warshel, A.; Barboy, N. J. Am. Chem. Soc. 1982, 104, 1469-1476.
29. Birge, R. R.; Hubbard, L. M. J. Am. Chem. Soc. 1980, 102, 2195-2205.
30. Humphrey, W.; Xu, D.; Sheves, M.; Schulten, K. J. Phys. Chem. 1995, 99, 14549-14560.
31. (a) Landau, L. D. Phys. Z. Sowjetunion 1932, 2, 46.
32. (b) Zener, C. Proc. R. Soc. London, Ser. A 1932, 137, 696.
33. Michl, J.; Bonacic-Koutecky, V. Electronic Aspects of Organic Photochemistry; Wiley: New York, 1990.
34. Bernardi, F.; Olivucci, M.; Robb, M. A. Chem. Soc. Rev. 1996, 25, 321.
35. (a) Celani, P.; Robb, M. A.; Garavelli, M.; Bernardi F.; Olivucci, M. Chem. Phys. Letters 1995, 243, 1-8.
36. (b) Garavelli, M.; Celani, P.; Fato, M.; Bearpark, M. J.; Smith, B. R.; Olivucci, M.; Robb, M. A. J. Phys. Chem. 1997, 101, 2023.
37. (a) Bernardi, F.; Celani, P.; Olivucci, M.; Robb, M. A.; Suzzi-Valli, G. J. Am. Chem. Soc. 1995, 117, 10531-10536.
38. (b) Bearpark, M. J.; Bernardi, F.; Olivucci, M.; Robb, M. A. Int. J. Quantum Chem. 1996, 60, 505-512.
39. (c) Bearpark, M. J.; Bernardi, F.; Olivucci, M.; Robb, M. A.; Smith, B. R. J. Am. Chem. Soc. 1996, 118, 5254-5260.
40. (d) Bearpark, M. J.; Robb, M. A.; Bernardi, F.; Olivucci M. Chem. Phys. Lett. 1994 217 513-519.
41. (e) Pauncz, R. Spin Eigenfunctions Plenum Press: New York, 1979.
42. (f) Bernardi, F.; Olivucci, M.; McDouall, J. J. W.; Robb, M. A. J. Chem. Phys. 1988, 89, 6365-6375.
43. Olivucci, M.; Bernardi, F.; Celani, P.; Ragazos, I. N.; Robb, M. A. J. Am. Chem. Soc. 1994, 116, 1077-1085.
44. In this region, the standard methods for computing steepest descent lines would fail to locate the correct relaxation path (e.g., these methods usually retain the symmetry of the initial structure). Accordingly, for this region, we have computed the MEP using a computational strategy based upon a series of IRD optimizations performed at increasing values of the distance (radius of the hypersphere) from the starting point.
45. Schlegel, H. B. J. Chem. Soc., Faraday Trans. 1994, 90, 1569-1574.
46. 32d) yield the same charge distribution. Thus, in Figure 5 we report Mulliken charges only.
47. (b) Computed with the program: NBO Version 3.1, Glendening, E. D.; Reed, A. E. Carpenter, J. E.; Weinhold, F. See also: Reed, A. E.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211).
48. (b) Computed with the program: NBO Version 3.1, Glendening, E. D.; Reed, A. E. Carpenter, J. E.; Weinhold, F. See also: Reed, A. E.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211).
49. (c) See: Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361.
50. (d) See: Besler, B. H.; Metz, K. M., Jr.; Kollman, P. A. J. Comput. Chem. 1990, 11, 431.
51. (a) Salem, L.; Bruckmann, P. Nature 1975, 258, 526-528.
52. (b) Salem, L. Acc. Chem. Res. 1979, 12, 87-92.
53. These surfaces have been computed using ab initio MC-SCF theory with a 6-31G* basis set. We are grateful to Dr. Barbara Frabboni for providing these data.
54. (a) Wang, Q.; Kochendoerfer, G. G.; Schoenlein, R. W.; Verdegem, P. J. E.; Lugtenburg, J.; Mathies, R. A.; Shank, C. V. J. Phys. Chem. 1996, 100, 17388-17394.
55. (b) Schoenlein, R. W.; Peteanu, L. A.; Wang, Q.; Mathies, R. A.; Shank, C. V. J. Phys. Chem. 1993, 97, 12087-12092.
56. 2·dm(s)/ds = -dE(s)/ds where s is the photoisomerization coordinate and m(s) and E(S) are the corresponding effective reduced mass and potential energy along the composite MEP series of FC →IC → trans-product.
57. + configurations there is a flat region centered on stretched structures. The detailed topology of this region will be presented in a more technical paper.
58. Warshel, A. Nature 1976, 260, 679-683.
59. Zhang, H.; Lerro, K. A.; Yamamoto, T.; Lien, T. H.; Sastry, L.; Gawinowicz, M. A.; Nakanishi, K. J. Am. Chem. Soc. 1994, 116, 10165-10173.