Quantum chemical study of electronic and structural properties of retinal and some aromatic analogs

Journal of Chemical Physics

Volumn 125, Issue 14, 2006, Pages

  Savedra, Ranylson M L ^a   Pinto, Melissa F S ^a   Trsic, Milan ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ANALOGS; ATOMIC CHARGES; ELECTROSTATIC POTENTIAL; MOLECULAR DEVICES; TRANSITION ENERGIES;

ELECTRONIC PROPERTIES; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; SPECTROSCOPIC ANALYSIS;

AROMATIC COMPOUNDS;

DRUG DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; RETINAL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; ULTRAVIOLET SPECTROPHOTOMETRY;

MODELS, MOLECULAR; POLYCYCLIC HYDROCARBONS, AROMATIC; QUANTUM THEORY; RETINALDEHYDE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 33750012619     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.2354498     Document Type: Article

References (52)

1. T. Ebrey and Y. Koutalos, Prog. Retin Eye Res. 20, 49 (2001).
2. M. I. Pepe, Prog. Retin Eye Res. 20, 733 (2001).
3. R. R. Birge, Annu. Rev. Phys. Chem. 41, 683 (1990).
4. L. Lensu, M. Frydrych, J. Parkkinen, S. Parkkinen, and T. Jaaskelainen, Opt. Mater. (Amsterdam, Neth.) 27, 57 (2004); A. A. Khodonov, S. V. Eremin, J. L. Lokship, V. I. Shvets, O. V. Demina, L. V. Khitrina, and A. D. Kaulen, J. Bioorg. Chem. 22, 640 (1996).
5. L. Lensu, M. Frydrych, J. Parkkinen, S. Parkkinen, and T. Jaaskelainen, Opt. Mater. (Amsterdam, Neth.) 27, 57 (2004); A. A. Khodonov, S. V. Eremin, J. L. Lokship, V. I. Shvets, O. V. Demina, L. V. Khitrina, and A. D. Kaulen, J. Bioorg. Chem. 22, 640 (1996).
6. E. Karnaukhova, S. Hu, R. Boonyasai, Q. Tan, and K. Nakanishi, Bioorg Khim. 27, 372 (1999).
7. D. Ivanova, V. Kolev, T. Lazarova, and E. Padrós, Tetrahedron Lett. 40, 2645 (1999).
8. R. R. Birge, J. A. Bennett, L. M. Hubbard, H. L. Fang, B. M. Pierce, D. S. Kliger, and G. E. Leroi, J. Am. Chem. Soc. 104, 2519 (1982).
9. J. R. Tallent, J. R. Birge, C. F. Zhang, E. Wenderholm, and R. R. Birge, Photochem. Photobiol. 56, 935 (1992).
10. E. J. Larson and C. K. Johnson, J. Phys. Chem. B 103, 10917 (1999).
11. E. J. Larson, S. J. Pyszczynski, and C. K. Johnson, J. Phys. Chem. A 105, 8136 (2001).
12. K. Ishii, S. Takeuchi, and T. Tahara, Chem. Phys. Lett. 418, 307 (2006).
13. S. Takeuchi and T. Tahara, J. Phys. Chem. A 101, 3052 (1997).
14. S. Yamaguchi and H. Hamaguchi, J. Phys. Chem. A 104, 4272 (2000).
15. S. Yamaguchi and T. Tahara, Chem. Phys. Lett. 376, 237 (2003).
16. B. Hudson and B. Kohler, Annu. Rev. Phys. Chem. 25, 437 (1974).
17. M. F. S. Pinto and M. Trsic, Internet Electron. J. Mol. Des. 3, 45 (2004).
18. R. Giro and D. S. Galvão, Int. J. Quantum Chem. 95, 252 (2003).
19. R. E. Stratmann, G. E. Scuseria, and M. J. Frisch, J. Chem. Phys. 0021-9606 10.1063/1.477483 109, 8218 (1998); K. B. Wiberg, R. E. Stratmann, and M. J. Frisch, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(98)01119-1 297, 60 (1998); R. Bauernschmitt and R. Ahlrichs, Chem. Phys. Lett. 0009-2614 10.1016/0009-2614(96)00440-X 256, 454 (1996); E. Runge and E. K. U. Gross, Phys. Rev. Lett. 0031-9007 10.1103/PhysRevLett.52.997 52, 997 (1984); M. E. Casida, J. Chem. Phys. 0021-9606 10.1063/1.1836757 122, 054111 (2005); M. E. Casida and D. R. Salahub, J. Chem. Phys. 0021-9606 10.1063/1.1319649 113, 8918 (2000); H. Appel, E. K. U. Gross, and K. Burke, Phys. Rev. Lett. 90, 043005 (2003).
20. R. E. Stratmann, G. E. Scuseria, and M. J. Frisch, J. Chem. Phys. 0021-9606 10.1063/1.477483 109, 8218 (1998); K. B. Wiberg, R. E. Stratmann, and M. J. Frisch, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(98)01119-1 297, 60 (1998); R. Bauernschmitt and R. Ahlrichs, Chem. Phys. Lett. 0009-2614 10.1016/0009-2614(96)00440-X 256, 454 (1996); E. Runge and E. K. U. Gross, Phys. Rev. Lett. 0031-9007 10.1103/PhysRevLett.52.997 52, 997 (1984); M. E. Casida, J. Chem. Phys. 0021-9606 10.1063/1.1836757 122, 054111 (2005); M. E. Casida and D. R. Salahub, J. Chem. Phys. 0021-9606 10.1063/1.1319649 113, 8918 (2000); H. Appel, E. K. U. Gross, and K. Burke, Phys. Rev. Lett. 90, 043005 (2003).
21. R. E. Stratmann, G. E. Scuseria, and M. J. Frisch, J. Chem. Phys. 0021-9606 10.1063/1.477483 109, 8218 (1998); K. B. Wiberg, R. E. Stratmann, and M. J. Frisch, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(98)01119-1 297, 60 (1998); R. Bauernschmitt and R. Ahlrichs, Chem. Phys. Lett. 0009-2614 10.1016/0009-2614(96)00440-X 256, 454 (1996); E. Runge and E. K. U. Gross, Phys. Rev. Lett. 0031-9007 10.1103/PhysRevLett.52.997 52, 997 (1984); M. E. Casida, J. Chem. Phys. 0021-9606 10.1063/1.1836757 122, 054111 (2005); M. E. Casida and D. R. Salahub, J. Chem. Phys. 0021-9606 10.1063/1.1319649 113, 8918 (2000); H. Appel, E. K. U. Gross, and K. Burke, Phys. Rev. Lett. 90, 043005 (2003).
22. R. E. Stratmann, G. E. Scuseria, and M. J. Frisch, J. Chem. Phys. 0021-9606 10.1063/1.477483 109, 8218 (1998); K. B. Wiberg, R. E. Stratmann, and M. J. Frisch, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(98)01119-1 297, 60 (1998); R. Bauernschmitt and R. Ahlrichs, Chem. Phys. Lett. 0009-2614 10.1016/0009-2614(96)00440-X 256, 454 (1996); E. Runge and E. K. U. Gross, Phys. Rev. Lett. 0031-9007 10.1103/PhysRevLett.52.997 52, 997 (1984); M. E. Casida, J. Chem. Phys. 0021-9606 10.1063/1.1836757 122, 054111 (2005); M. E. Casida and D. R. Salahub, J. Chem. Phys. 0021-9606 10.1063/1.1319649 113, 8918 (2000); H. Appel, E. K. U. Gross, and K. Burke, Phys. Rev. Lett. 90, 043005 (2003).
23. R. E. Stratmann, G. E. Scuseria, and M. J. Frisch, J. Chem. Phys. 0021-9606 10.1063/1.477483 109, 8218 (1998); K. B. Wiberg, R. E. Stratmann, and M. J. Frisch, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(98)01119-1 297, 60 (1998); R. Bauernschmitt and R. Ahlrichs, Chem. Phys. Lett. 0009-2614 10.1016/0009-2614(96)00440-X 256, 454 (1996); E. Runge and E. K. U. Gross, Phys. Rev. Lett. 0031-9007 10.1103/PhysRevLett.52.997 52, 997 (1984); M. E. Casida, J. Chem. Phys. 0021-9606 10.1063/1.1836757 122, 054111 (2005); M. E. Casida and D. R. Salahub, J. Chem. Phys. 0021-9606 10.1063/1.1319649 113, 8918 (2000); H. Appel, E. K. U. Gross, and K. Burke, Phys. Rev. Lett. 90, 043005 (2003).
24. R. E. Stratmann, G. E. Scuseria, and M. J. Frisch, J. Chem. Phys. 0021-9606 10.1063/1.477483 109, 8218 (1998); K. B. Wiberg, R. E. Stratmann, and M. J. Frisch, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(98)01119-1 297, 60 (1998); R. Bauernschmitt and R. Ahlrichs, Chem. Phys. Lett. 0009-2614 10.1016/0009-2614(96)00440-X 256, 454 (1996); E. Runge and E. K. U. Gross, Phys. Rev. Lett. 0031-9007 10.1103/PhysRevLett.52.997 52, 997 (1984); M. E. Casida, J. Chem. Phys. 0021-9606 10.1063/1.1836757 122, 054111 (2005); M. E. Casida and D. R. Salahub, J. Chem. Phys. 0021-9606 10.1063/1.1319649 113, 8918 (2000); H. Appel, E. K. U. Gross, and K. Burke, Phys. Rev. Lett. 90, 043005 (2003).
25. R. E. Stratmann, G. E. Scuseria, and M. J. Frisch, J. Chem. Phys. 0021-9606 10.1063/1.477483 109, 8218 (1998); K. B. Wiberg, R. E. Stratmann, and M. J. Frisch, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(98)01119-1 297, 60 (1998); R. Bauernschmitt and R. Ahlrichs, Chem. Phys. Lett. 0009-2614 10.1016/0009-2614(96)00440-X 256, 454 (1996); E. Runge and E. K. U. Gross, Phys. Rev. Lett. 0031-9007 10.1103/PhysRevLett.52.997 52, 997 (1984); M. E. Casida, J. Chem. Phys. 0021-9606 10.1063/1.1836757 122, 054111 (2005); M. E. Casida and D. R. Salahub, J. Chem. Phys. 0021-9606 10.1063/1.1319649 113, 8918 (2000); H. Appel, E. K. U. Gross, and K. Burke, Phys. Rev. Lett. 90, 043005 (2003).
26. J. Schirmer and A. Dreuw, Phys. Rev. A (Submitted), cond-mat/0602020
27. J. J. P. Stewart, J. Comput. Chem. 0192-8651 10.1002/jcc.540100209 10, 221 (1989); J. J. P. Stewart, J. Comput. Chem. 10, 209 (1989).
28. J. J. P. Stewart, J. Comput. Chem. 0192-8651 10.1002/jcc.540100209 10, 221 (1989); J. J. P. Stewart, J. Comput. Chem. 10, 209 (1989).
29. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc. 107, 3902 (1985).
30. A. Szabo and N. S. Ostlund, Modern Quantum Chemistry (McGraw-Hill, New York, 1996).
31. W. J. Hehre, L. Radom, P. V. R. Schleyer, and J. A. Pople, Ab initio Molecular Orbital Theory (Wiley, New York, 1986).
32. R. S. Becker, Photochem. Photobiol. 48, 369 (1988).
33. M. J. Frisch, G. W. Trucks, H. B. Schlegel, GAUSSIAN 03, Revision B.04, Gaussian, Inc., Wallingford, CT, 2004.
34. M. C. Zerner, G. H. Loew, R. F. Kircner, and U. T. Mueller-Westerhoff, J. Am. Chem. Soc. 102, 589 (1980).
35. G. R. Hutchison, M. A. Ratner, and T. J. Marks, J. Phys. Chem. A 106, 10596 (2002).
36. T. Hamanaka, T. Mitsui, T. Ashida, and M. Kakudo, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 28, 214 (1972).
37. N. J. Turro, Modern Molecular Photochemistry, 1st ed. (Science Books, Sausalito, CA, 1991).
38. V. F. Traven, Frontier Orbitals and Properties of Organic Molecules, 1st ed. (Ellis Horwood, New York, 1992).
39. I. Levine, Quantum Chemistry, 5th ed. (Prentice Hall, New York, 2000).
40. F. L. Pilar, Elementary Quantum Chemistry, 2nd ed. (Dover, New York, 2001).
41. S. Wolfe, Z. Shi, C. E. Brion, J. Rolke, Y. Zheng, G. Cooper, D. P. Chong, and C. Hu, Can. J. Chem. 0008-4042 80, 222 (2002); Y. Zheng, J. Rolke, G. Cooper, and C. E. Brion, J. Electron Spectrosc. Relat. Phenom. 0368-2048 123, 377 (2002); R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules (Oxford University Press, New York, 1989); D. P. Chong, O. V. Gritsenko, and E. J. Baerends, J. Chem. Phys. 0021-9606 10.1063/1.1430255 116, 1760 (2002); R. Stowasser and R. Hoffmann, J. Am. Chem. Soc. 121, 3414 (1999); J. C. Cramer, Essentials of Computational Chemistry: Theories and Models, 1st ed. (Wiley, Ontario, 2002).
42. S. Wolfe, Z. Shi, C. E. Brion, J. Rolke, Y. Zheng, G. Cooper, D. P. Chong, and C. Hu, Can. J. Chem. 0008-4042 80, 222 (2002); Y. Zheng, J. Rolke, G. Cooper, and C. E. Brion, J. Electron Spectrosc. Relat. Phenom. 0368-2048 123, 377 (2002); R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules (Oxford University Press, New York, 1989); D. P. Chong, O. V. Gritsenko, and E. J. Baerends, J. Chem. Phys. 0021-9606 10.1063/1.1430255 116, 1760 (2002); R. Stowasser and R. Hoffmann, J. Am. Chem. Soc. 121, 3414 (1999); J. C. Cramer, Essentials of Computational Chemistry: Theories and Models, 1st ed. (Wiley, Ontario, 2002).
43. S. Wolfe, Z. Shi, C. E. Brion, J. Rolke, Y. Zheng, G. Cooper, D. P. Chong, and C. Hu, Can. J. Chem. 0008-4042 80, 222 (2002); Y. Zheng, J. Rolke, G. Cooper, and C. E. Brion, J. Electron Spectrosc. Relat. Phenom. 0368-2048 123, 377 (2002); R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules (Oxford University Press, New York, 1989); D. P. Chong, O. V. Gritsenko, and E. J. Baerends, J. Chem. Phys. 0021-9606 10.1063/1.1430255 116, 1760 (2002); R. Stowasser and R. Hoffmann, J. Am. Chem. Soc. 121, 3414 (1999); J. C. Cramer, Essentials of Computational Chemistry: Theories and Models, 1st ed. (Wiley, Ontario, 2002).
44. S. Wolfe, Z. Shi, C. E. Brion, J. Rolke, Y. Zheng, G. Cooper, D. P. Chong, and C. Hu, Can. J. Chem. 0008-4042 80, 222 (2002); Y. Zheng, J. Rolke, G. Cooper, and C. E. Brion, J. Electron Spectrosc. Relat. Phenom. 0368-2048 123, 377 (2002); R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules (Oxford University Press, New York, 1989); D. P. Chong, O. V. Gritsenko, and E. J. Baerends, J. Chem. Phys. 0021-9606 10.1063/1.1430255 116, 1760 (2002); R. Stowasser and R. Hoffmann, J. Am. Chem. Soc. 121, 3414 (1999); J. C. Cramer, Essentials of Computational Chemistry: Theories and Models, 1st ed. (Wiley, Ontario, 2002).
45. S. Wolfe, Z. Shi, C. E. Brion, J. Rolke, Y. Zheng, G. Cooper, D. P. Chong, and C. Hu, Can. J. Chem. 0008-4042 80, 222 (2002); Y. Zheng, J. Rolke, G. Cooper, and C. E. Brion, J. Electron Spectrosc. Relat. Phenom. 0368-2048 123, 377 (2002); R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules (Oxford University Press, New York, 1989); D. P. Chong, O. V. Gritsenko, and E. J. Baerends, J. Chem. Phys. 0021-9606 10.1063/1.1430255 116, 1760 (2002); R. Stowasser and R. Hoffmann, J. Am. Chem. Soc. 121, 3414 (1999); J. C. Cramer, Essentials of Computational Chemistry: Theories and Models, 1st ed. (Wiley, Ontario, 2002).
46. S. Wolfe, Z. Shi, C. E. Brion, J. Rolke, Y. Zheng, G. Cooper, D. P. Chong, and C. Hu, Can. J. Chem. 0008-4042 80, 222 (2002); Y. Zheng, J. Rolke, G. Cooper, and C. E. Brion, J. Electron Spectrosc. Relat. Phenom. 0368-2048 123, 377 (2002); R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules (Oxford University Press, New York, 1989); D. P. Chong, O. V. Gritsenko, and E. J. Baerends, J. Chem. Phys. 0021-9606 10.1063/1.1430255 116, 1760 (2002); R. Stowasser and R. Hoffmann, J. Am. Chem. Soc. 121, 3414 (1999); J. C. Cramer, Essentials of Computational Chemistry: Theories and Models, 1st ed. (Wiley, Ontario, 2002).
47. A. A. Khodonov, S. V. Eremin, J. L. Lokshin, V. I. Shvets, O. V. Demina, V. Khitrina, and A. D. Kaulen, Russ. J. Bioorg. Chem. 22, 640 (1996).
48. S. Yamaguchi and H. O. Hamaguchi, J. Chem. Phys. 109, 1397 (1998).
49. H. H. Jaffe and M. Orchin, Theory and Applications of Ultraviolet Spectroscopy (Wiley, New York, 1964); R. S. Mulliken, J. Chem. Phys. 7, 14 (1939).
50. H. H. Jaffe and M. Orchin, Theory and Applications of Ultraviolet Spectroscopy (Wiley, New York, 1964); R. S. Mulliken, J. Chem. Phys. 7, 14 (1939).
51. E. Hendrickx, K. Clays, A. Persoons, C. Dehu, and J. L. Bredas, J. Am. Chem. Soc. 117, 3547 (1995).
52. E. J. Larson, L. A. Friesen, and C. K. Johnson, Chem. Phys. Lett. 265, 161 (1997).