Theoretical Characterization of Intramolecular Proton Transfer in the Ground and the Lowest-Lying Triplet Excited States of 1-Amino-3-Propenal: A Methodological Comparison

Journal of Computational Chemistry

Volumn 21, Issue 4, 2000, Pages 257-269

  Forés, Marta ^a   Duran, Miquel ^a   Solà, Miquel ^a   Adamowicz, Ludwik ^b  

^a UNIVERSITY OF GIRONA   (Spain)

^b University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001244892     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(200003)21:4<257::AID-JCC2>3.0.CO;2-F     Document Type: Article

References (101)

1. (a) Chou, P.; McMorrow, D.; Aartsma, T. J.; Kasha, M. J Phys Chem 1984, 88, 4596;
2. (b) Parthenopoulos, D. A.; McMorrow, D.; Kasha, M. J Phys Chem 1991, 95, 2668;
3. (c) Macinnis, J. M.; Kasha, M. Chem Phys Lett 1988, 151, 375.
4. Parthenopoulos, D. A.; Kasha, M. Chem Phys Lett 1988, 146, 77.
5. (a) Ernsting, N. P.; Nikolaus, B. Appl Phys B 1986, 39, 155;
6. (b) Liphardt, M.; Goonesekera, A.; Jones, B. E.; Ducharme, S.; Takacs, J. M.; Zhang, L. Science 1994, 263, 367;
7. (c) Douhal, A.; Sastre, R. Chem Phys Lett 1994, 219, 91.
8. Martinez, M. L.; Cooper, W. C.; Chou, P.-T. Chem Phys Lett 1992, 193, 151.
9. Otterstedt, J.-E. A. J Chem Phys 1973, 58, 5716.
10. Ormson, S. M.; Brown, R. G. Prog React Kinet 1994, 19, 45.
11. Werner, T. J Phys Chem 1979, 83, 320.
12. Löwdin, P.-O. Rev Mod Phys 1963, 35, 724.
13. Pullman, B.; Pullman, A. Adv Heterocycl Chem 1971, 13, 77.
14. Douhal, A.; Lahmani, F.; Zewail, A. H. Chem Phys 1996, 207, 477.
15. Duan, X.; Scheiner, S. Chem Phys Lett 1993, 204, 36.
16. Sobolewski, A. L.; Domcke, W. Chem Phys Lett 1993, 211, 82.
17. Sobolewski, A. L. Chem Phys Lett 1993, 211, 293.
18. Sobolewski, A. L.; Domcke, W. Chem Phys 1994, 184, 115.
19. Luth, K.; Scheiner, S. J Phys Chem 1994, 98, 3582.
20. Luth, K.; Scheiner, S. J Phys Chem 1995, 99, 7352.
21. Estévez, C. M.; Bach, R. D.; Hass, K. C.; Schneider, W. F. J Am Chem Soc 1997, 119, 5445.
22. Guallar, V.; Moreno, M.; Lluch, J. M.; Amat-Guerri, F.; Douhal, A. J Phys Chem 1996, 100, 19789.
23. Sobolewski, A. L.; Adamowicz, L. Chem Phys 1996, 213, 181.
24. Sobolewski, A. L.; Adamowicz, L. Chem Phys 1995, 193, 67.
25. Sobolewski, A. L.; Adamowicz, L. Chem Phys Lett 1995, 234, 94.
26. Sobolewski, A. L.; Adamowicz, L. J Phys Chem 1995, 99, 14277.
27. Sobolewski, A. L.; Adamowicz, L. J Chem Phys 1995, 102, 5708.
28. Scheiner, S.; Kar, T.; Cuma, M. J Phys Chem A 1997, 101, 5901.
29. Barone, V.; Adamo, C. J Chem Phys 1996, 105, 11007.
30. Forés, M.; Duran, M.; Solà, M. Chem Phys 1998, 234, 1.
31. Hass, K. C.; Schneider, W. F.; Estévez, C. M.; Bach, R. D. Chem Phys Lett 1996, 263, 414.
32. Forés, M.; Duran, M.; Solà, M.; Adamowicz, L. J Phys Chem A 1999, 103, 4413.
33. Kieninger, M.; Suhai, S. Int J Quantum Chem 1994, 52, 465.
34. Van Duijneveldt-van de Rijdt, J. G. C. M.; Van Duijneveldt, F. B. J. Chem Phys 1992, 97, 5019.
35. Laforgue, A.; Brucena-Grimbert, C.; Laforghe-Kantzer, D.; Del Re, G.; Barone, V. J Phys Chem 1986, 86, 4436.
36. Scheiner, S. Acc Chem Res 1985, 18, 174.
37. Rovira, M. C.; Scheiner, S. J Phys Chem 1995, 99, 9854.
38. Scheiner, S. In: Truhlar, D. G., ed. Hydrogen Bonding. A Theoretical Perspective; Oxford University Press: New York, 1997.
39. Del Bene, J. G.; Ditchfield, R.; Pople, J. A. J Chem Phys 1971, 55, 2236.
40. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J Phys Chem 1992, 96, 135.
41. Grimme, S. Chem Phys Lett 1996, 259, 128.
42. Stanton, J. F.; Gauss, J.; Ishikawa, N.; Head-Gordon, M. J Chem Phys 1995, 103, 4160.
43. Barone, V.; Adamo, C. Int J Quantum Chem 1997, 61, 429.
44. Schlegel, H. B. J Chem Phys 1986, 84, 4530.
45. Cizek, J. J Chem Phys 1966, 45, 4256.
46. Taylor, P. R.; Bacskay, G. B.; Hush, N. S.; Hurley, A. C. Chem Phys Lett 1976, 41, 444.
47. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int J Quantum Chem 1978, 14, 545.
48. (a) Bartlett, R. J.; Purvis, G. D. Int J Quantum Chem 1978, 14, 561;
49. (b) Bartlett, R. J. Ann Rev Phys Chem 1981, 32, 359.
50. Purvis, G. D.; Bartlett, R. J. J Chem Phys 1982, 76, 1910.
51. Urban, M.; Noga, J.; Cole, S. J.; Bartlett, R. J. J Chem Phys 1985, 83, 4041.
52. Raghavachari, K. J Chem Phys 1985, 82, 4607.
53. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J Chem Phys 1987, 87, 5968.
54. Wolinski, K.; Pulay, P. J Chem Phys 1989, 90, 3647.
55. Chen, W.; Schlegel, H. B. J Chem Phys 1994, 101, 5957.
56. Sekino, H.; Barlett, R. J. J Chem Phys 1985, 82, 4225.
57. Roos, B. O. In: Lawley, K. P., ed. Advances in Chemical Physics. Ab initio Methods in Quantum Chemistry. Part 2; Wiley: New York, 1987 399.
58. Andersson, K.; Malmqvist, P.-Å.; Roos, B. O.; Sadlej, A. J.; Wolinski, K. J Phys Chem 1990, 94, 5483.
59. Andersson, K.; Malmqvist, P.-Å.; Roos, B. O. J Chem Phys 1992, 96, 1218.
60. Andersson, K.; Roos, B. O. In: Yarkony, R., ed. Modern Electron Structure Theory; Vol. 1; World Scientific: New York, 1994.
61. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, UK, 1989.
62. Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J Chem Phys 1993, 98, 5612.
63. Seminario, J. M.; Politzer, P. Modern Density Functional Theory: A Tool for Chemistry; Elsevier: New York, 1995.
64. Ziegler, T. Chem Rev 1991, 91, 651.
65. Cramer, C. J.; Dulles, F. J.; Giesen, D. J.; Almlöf, J. Chem Phys Lett 1995, 245, 165.
66. Kasha, M.; Heldt, J.; Gormin, D. J Phys Chem 1995, 99, 7281.
67. Wood, P. D.; Redmond, R. W. J Am Chem Soc 1996, 118, 4256.
68. (a) Al-Ansari, I. A. Z. J Lumin 1997, 71, 83;
69. (b) Das, S. K.; Bansal, A.; Dogra, S. K. Bull Chem Soc Jpn 1997, 70, 307;
70. (c) Mosquera, M.; Penedo, J. C.; Ríos-Rodríguez, M. C.; Rodríguez-Prieto, F. J Phys Chem 1996, 100, 5398.
71. Roberts, E. L.; Dey, J.; Warner, I. M. J Phys Chem 1996, 100, 19681.
72. Yang, G.; Morlet-Savary, F.; Peng, Z.; Wu, S.; Fouassier, J. P. Chem Phys Lett 1996, 256, 536.
73. Becke, A. D. J Chem Phys 1993, 98, 5648.
74. Lee, C.; Yang, W.; Parr, R. G. Phys Rev B 1988, 37, 785.
75. Catalán, J.; Palomar, J.; de Paz, J. L. G. J Phys Chem A 1997, 101, 7914.
76. Novoa, J. J.; Sosa, C. J Phys Chem 1995, 99, 15837.
77. Pudzianowski, A. T. J Phys Chem 1996, 100, 4781.
78. del Bene, J. E.; Person, W. B.; Szczepaniak, K. J Phys Chem 1995, 99, 10705.
79. In the case of the CASSCF TS geometry, the frequency calculations were calculated numerically using the STO-3G basis set.
80. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem Phys Lett 1989, 157, 479.
81. Bartlett, R. J.; Watts, J. D.; Kucharski, S. A.; Noga, J. Chem Phys Lett 1990, 165, 513.
82. Wang, J.; Becke, A. D.; Smith, V. H., Jr. J Chem Phys 1995, 102, 3477.
83. Baker, J.; Scheiner, A.; Andzelm, J. Chem Phys Lett 1993, 216, 380.
84. Wang, J.; Eriksson, L. A.; Boyd, R. J.; Shi, Z.; Johnson, B. G. J Phys Chem 1994, 98, 1844.
85. Adamo, C.; Barone, V.; Fortunelli, A. J Phys Chem 1994, 98, 8648.
86. Forés, M.; Adamowicz, L. J Comput Chem 1999, 20, 1422.
87. Sobolevvski, A. L.; Domcke, W. J Phys Chem A 1999, 103, 4494.
88. Dunning, T. H., Jr.; Hay, P. J. In: Schaefer, H. F., III, ed. Methods of Electronic Structure Theory; Plenum: New York, 1977.
89. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. V. R. J Comput Chem 1983, 4, 294.
90. Andersson, K.; Fülscher, M. P.; Karlström, G.; Lindh, R.; Malmqvist, P.-Å.; Olsen, J.; Roos, B. O.; Sadlej, A. J.; Blomberg, M. R. A.; Siegbahn, P. E. M.; Kellö, V.; Noga, J.; Urban, M.; Widmark, P.-O. MOLCAS, Version 3, Lund University, Sweden, 1994.
91. Andersson, K.; Blomberg, M. R. A.; Fülscher, M. P.; Karlström, G.; Lindh, R.; Malmqvist, P.-Å.; Neogrády, P.; Olsen, J.; Roos, B. O.; Sadlej, A. J.; Sadlej, M.; Schütz, M.; Seijo, L.; Serrano-Andrés, L.; Siegbahn, P. E. M.; Widmark, P.-O. MOLCAS, Version 4, Lund University, Sweden, 1997.
92. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. C.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B.; Nanayakkara, A.; Challacombe, M.; 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.2; Gaussian, Inc., Pittsburgh, PA, 1995.
93. Duan, X.; Scheiner, S. Chem Phys Lett 1993, 204, 36.
94. Sim, F.; St-Amant, A.; Papai, I.; Salahub, D. R. J Am Chem Soc 1992, 114, 4391.
95. Jursic, B. S. J Mol Struct (Theochem) 1997, 417, 89.
96. Zhang, Q.; Bell, R.; Truong, T. N. J Phys Chem 1995, 99, 592.
97. See ref. 26 for a depiction of the HF orbitals involved in the nπ* and ππ* transitions.
98. Baltan, E. E.; Schaefer, H. F., III J Am Chem Soc 1993, 115, 6207.
99. Love, D. E.; Nachligallova, D.; Jordan, K. D.; Lawson, J. M.; Paddon-Row, M. N. J Am Chem Soc 1996, 118, 1235.
100. Hadad, C. M.; Foresman, J. B.; Wiberg, K. B. J Phys Chem 1993, 97, 4293.
101. Kar, T.; Scheiner, S.; Cuma, M. J Chem Phys 1999, 111, 849.