Calculation of the vibrational spectra of linear tetrapyrroles. 2. Resonance Raman spectra of hexamethylpyrromethene monomers

Journal of Physical Chemistry B

Volumn 104, Issue 46, 2000, Pages 10885-10899

  Mroginski, Maria Andrea ^a,b   Németh, Károly ^a   Magdé, Ildikó ^a,c   Müller, Martin ^a   Robben, Uwe ^a   Della Védova, Carlos ^b   Hildebrandt, Peter ^a   Mark, Franz ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^b FACULTAD DE CIENCIAS EXACTAS   (Argentina)

^c GEDEON RICHTER LTD   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; DIMERS; ELECTRON TRANSITIONS; GROUND STATE; HYDROGEN BONDS; MOLECULAR VIBRATIONS; MONOMERS; OPTIMIZATION; QUANTUM THEORY; RAMAN SPECTROSCOPY; RESONANCE;

HEXAMETHYLPYRROMETHENE;

NITROGEN COMPOUNDS;

EID: 17444453636     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp000444h     Document Type: Article

References (80)

1. (a) Scheer, H. Angew. Chem., Int. Ed. Engl. 1981, 20, 241.
2. (b) MacColl, R.; Guard-Friar, D. Phycobiliproteins; CRC Press: Boca Raton, Fl, 1987.
3. Holzwarth, A. R. Q. Rev. Biophys. 1989,22,239
4. Schaffner, K.; Braslavsky, S. E.; Holzwarth, A. R. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H. J., Dürr, H., Eds.; VCH: Weinheim, 1991; p 421.
5. (a) Fodor, S. P. A.; Lagarias, J. C.; Mathies, R. A. Photochetn. Photobiol. 1988, 48, 129.
6. (b) Fodor, S. P. A.; Lagarias, J. C.; Mathies, R. A. Biochemistry 1990,29, 11141.
7. Andel, F., Ill; Lagarias, J. C.; Mathies, R. A. Biochemistry 1996, 55, 15997.
8. (a) Hildebrandt, P.; Hoffmann, A.; Lindemann, P.; Heibel, G.; Braslavsky, S. E.; Schaffner, K.; Schrader, B. Biochemistry 1992,37,7957.
9. (b) Matysik, J.; Hildebrandt, P.; Schlamann, W.; Braslavsky, S. E.; Schaffner, K. Biochemistry 1995, 34, 10497.
10. Kneip, K., Mozley, D., Hildebrandt, P.; Gärtner, W.; Braslavsky, S. E.; Schaffner, K. FEBS Lett. 1997,414, 23.
11. Kneip, C.; Hildebrandt, P.; Schlamann, W.; Braslavsky, S. E.; Mark, F.; Schaffner, K. Biochemistry 1999, 38, 15185.
12. (a) Tokutomi, S.; Mizutani, Y.; Anni, H.; Kitagawa, T. FEBS Lett. 1990, 269, 341.
13. (b) Mizutani, Y.; Tokutomi, S.; Aoyagi, K.; Horitsu, K.; Kitagawa, T. Biochemistry 1991, 30, 10693.
14. Mizutani, Y.; Tokutomi, S.; Kitagawa, T. Biochemistry 1994, 33, 153.
15. Szalontai, B.; Combos, Z.; Csizmadia, V.; Bagyinka, C.; Lutz, M. Biochemistry 1994, 33, 11823.
16. Smit, K.; Matysik, J.; Hildebrandt, P.; Mark, F. J. Phys. Chem. 1993,97, 11887.
17. Magdó, L; Nérneth, K.; Mark, F.; Hildebrandt, P.; Schaffner, K. J. Phys. Chem. A 1999, 103, 289.
18. Kneip, C.; Hildebrandt, P.; Németh, K.; Mark, F.; Schaffner, K. Chem. Phys. Lett. 1999, 311, 479.
19. (a) Pulay, P.; Fogarasi, G.; Pongor, G.; Boggs, J. E.; Vargha, A. J. Am. Chem. Soc. 1983, 705,7037.
20. (b) Rauhut, G.; Pulay, P. J. Phys. Chem. 1995, 99, 3093.
21. (a) Kozlowski, P. M.; Zgierski, M. Z.; Pulay, P. Chem. Phys. Lett. 1995, 247, 379.
22. (b) Kozlowski, P. M.; Jarzecki, A. A.; Pulay, P.; Li- X.-Y.; Zgierski, M. Z. J. Phys. Chem. 1996, 700, 13985.
23. Kozlowski, P. M.; Jarzecki, A. A.; Pulay, P. J. Phys. Chem. 1996, 700, 7007.
24. (a) Spiro, T. G.; Kozlowski, P. M.; Zgierski, M. Z. J. Roman Spectrosc. 1998, 29, 869.
25. (b) Kozlowski, P. M.; Rush, T. S., III; Jarzecki, A. A.; Zgierski, M. Z.; Chase, B.; Piffat, C.; Ye, B.-H.; Li, X.-Y.; Pulay, P.; Spiro, T. G. J. Phys. Chem. A 1999, 70J, 1357.
26. Hizhnyakov, V.; Tehver, I. Phys. Status Solidi 1967, 27, 755.
27. (a) Champion, P. M.; Albrecht, A. C. J. Phys. Chem. 1980, 72, 6498.
28. (b) Stallard, B. R.; Champion, P. M.; Callis, P. R.; Albrecht, A. C. J. Phys. Chem. 1983, 78, 712.
29. Chan, C. K.; Page, J. B. J. Chem. Phys. 1983, 79, 5234.
30. (a) Peticolas, W. L.; Rush, T., Ill J. Comput. Chem. 1995,16, 1261.
31. (b) Rush, T., Ill; Peticolas, W. L. J. Phys. Chem. 1995, 99, 14647.
32. Rush, T., Ill; Rumble, R.; Mukherjee, A.; Blackwood jr, M. E.; Spiro, T. G. J. Phys. Chem. 1996, 700, 12076.
33. Kumble, R.; Rush, T. S., Ill; Blackwood, M. E., Jr.; Kozlowski, P. M.; Spiro, T. G. J. Phys. Chem. B 1998, 702, 7280.
34. Kochendoerfer, G. G.; Wang, Z.; Oprian, D. D.; Mathies, R. A. Biochemistry 1997, 36, 6577.
35. Goddard, R.; Heinemann, O.; Krüger, C.; Mark, F. Manuscript in preparation.
36. Németh, K.; Kneip, C.; Mroginski, M. A.; Hildebrandt, P.; Mark, F. Manuscript in preparation.
37. Bullock, E.; Johnson, A. W.; Markham, E.; Shaw, K. B. J. Chem. Soc. 1958, 1430.
38. Badger, G. M.; Harris, R. L. N.; Jones, R. A. Aust. J. Chem. 1964, 17, 1002.
39. Fischer, H.; Wallach, B. Ann. Chem. 1926, 450, 109.
40. Johnson, A. W.; Kay, I. T.; Markham, E.; Price, R.; Shaw, K. B. J. Chem. Soc. 1959, 3416.
41. Guy, R. W.; Jones, R. A. Aust. J. Chem. 1965, 18, 363.
42. (a) Döpner, S.; Hildebrandt, P.; Rosell, F. L; Mauk, A. G. J. Am. Chem. Soc. 1998, 720, 11246.
43. (b) Wackerbaith, H.; Klar, U.; Günther, W.; Hildebrandt, P. Appl. Spectrosc. 1999, 53, 283.
44. 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. J. P.; Head-Gordon, M.; Gonzalez, C; Pople, J. A. GAUSSIAN 94. Revision B.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery jr., J. A.; Stratman, 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.; Baboul, A. G.; 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.; Gonzales, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
46. Becke, A. D. J. Phys. Chem. 1993, 98, 5648.
47. (a) Gross, E. K. U.; Dobson, J. F.; Petersilka, M. Topics Curr. Chem. 1996, 181, 81.
48. (b) Casida, M. E. In 'Theoretical and Computational Chemistry; Seminario, J. M., Ed.; Elsevier: Amsterdam, 1996; p 391.
49. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454.
50. Stratman, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
51. Van Gisbergen, S. J. A.; Snijders, J. G.; Baerends, E. J. Comput. Phys. Commun. 1999, 118, 119.
52. (a) Del Bene, J.; Jaffè, H. H. J. Chem. Phys. 1968, 48, 1807.
53. (b) Del Bene, J.; Jaffè, H. H. J. Chem. Phys. 1968, 48, 4050.
54. Albrecht, A. C. J. Chem. Phys. 1961, 49, 1144.
55. Dattagupta, J. K.; Meyer, E. F., Jr.; Cullen, D. L.; Falk, H.; Gergely, S. Acta Crystallogr. 1983, C39, 1384.
56. Haddon, R. C.; Raghavachari, K. J. Am. Chem. Soc. 1985, 707, 289.
57. (a) Bauernschmitt, R.; Ahlrichs, R.; Henrich, F. H.; Kappes, M. M. J. Ain. Chem. Soc. 1998, 120, 5052.
58. (b) Sundholm, D. Chem. Phys. Lett. 1999, 302, 480.
59. Van Gisbergen, S. J. A.; Groenveld, J. A.; Rosa, A.; Snijders, J. G.; Baerends, E. J. J. Phys. Chem. A 1999, 703, 6835.
60. Van Gisbergen, S. J. A.; Rosa, A.; Ricciardi, G.; Baerends, E. J. J. Chem. Phys. 1999, 111, 2499.
61. (e) Sundholm, D. Phys. Chem. Chem. Phys. 2000, 2, 2275.
62. Serrano-Andrés, L.; Merchán, M.; Rubio, M.; Roos, B. O. Chem. Phys. Lett. 1998, 295, 195.
63. Calculations with larger basis sets such as 6-31++G**, 6-31++G*, or 6-311++G** could not be completed with GAUSSIAN98 as the largest MO coefficient eventually exceeds the computational threshold of the program. Large coefficients arise for those unoccupied orbitals with strong contributions of diffuse basis functions. These orbitals have Rydberg characteristics and are of highly oscillatory form because of the orthogonality constraint to the manifold of lower lying orbitals.
64. Becke, A. D. Phys. Rev. 1988, A38, 3098.
65. Perdew, J. P. Phys. Rev. 1986, B33, 8822.
66. Since the HOMO and LUMO are localized in different parts of the molecule, i.e., in the pyrrolic ring and in the pyrroleninic ring and methine bridge, respectively, the transition moment and, hence, the oscillator strength are large for the HOMO -LUMO transition.
67. Compared to the B3LYP MOs, the BP86 MOs are raised in energy, however, the shifts are more pronounced for the HOMO -1 and HOMO - 2 compared to the HOMO so that the energy differences between these orbitals are reduced, which in turn may promote mixing of these MOs in the excited states.
68. For the HF/6-31G* ground state geometry HOMO-2 and HOMO-1 are inverted compared to B3LYP, BP86, and CNDO/S calculations based on the B3LYP/6-31G* geometry.
69. (a) Zilberg, S.; Kendler, S.; Haas, Y. J. Phys. Chem. 1996, 700, 10869.
70. (b) Slater, L. S.; Callis, P. R. J. Phys. Chem. 1995, 99, 8572.
71. Zgierski, M. Z.; Zerbetto, F. J. Chem. Phys. 1993, 98, 14.
72. (a) Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135.
73. (b) Hadad, C. M.; Foresman, J. B.; Wiberg, K. B. J. Phys. Chem. 1993, 97, 4293.
74. Stanton, J. F.; Gauss, J.; Ishikawa, N.; Head-Gordon, M. J. Chem. Phys. 1995, 103, 4160.
75. Pulay, P.; Fogarasi, G.; Pang, F.; Boggs, J. E. J. Am. Chem. Soc. 1979, 101, 2550.
76. (a) Peticolas, W. L.; Strommen, D. P.; Lakshminarayanan, V. J. Chem. Phys. 1980, 73,4185.
77. (b) Lagant, P.; Derremaux, P.; Vergoten, G.; Peticolas, W. L. J. Commit. Chem. 1991, 12, 731.
78. Gossauer, A. Die Chemie der Pyrrole; Springer-Verlag: Berlin, 1974; p 64.
79. Hildebrandt, P.; Tsuboi, M.; Spiro, T. G. J. Phys. Chem. 1990, 94, 2274.
80. Van Caillie, C.; Amos, R. D. Chem. Phys. Lett. 2000, 317, 159.