Quantum chemical characterization of singlet and triplet didehydroindenes

Journal of Physical Chemistry A

Volumn 105, Issue 10, 2001, Pages 2091-2098

  Cramer, Christopher J ^a   Thompson, Jason ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIDEHYDROINDENES;

PERTURBATION TECHNIQUES; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY;

ISOMERS;

EID: 0035868337     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp004379n     Document Type: Article

References (100)

1. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499.
2. Jordan, K. Theor. Chem. Acc. 2000, 103, 286.
3. Heilbronner, E.; Muszkat, K. A. J. Am. Chem. Soc. 1970, 92, 3818.
4. Hoffmann, R. Acc. Chem. Res. 1971, 4, 1.
5. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696.
6. Paddon-Row, M. N. Acc. Chem. Res. 1992, 15, 245.
7. Li, S.; Ma, J.; Jiang, Y. J. Phys. Chem. A 1997, 101, 5567.
8. Squires, R. R.; Cramer, C. J. J. Phys. Chem. A 1998, 102, 9072.
9. Cui, M.; Feng, J. K.; Zhang, H. X.; Ge, M. F.; Sun, C. C.; Zhang, J. P. Synth. Met. 1999, 100, 261.
10. Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235.
11. Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 11, 1387.
12. Myers, A. G. Tetrahedron Lett. 1987, 28, 4493.
13. Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995.
14. Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191.
15. Enediyne Antibiotics as Antitumor Agents; Borders, D. B., Doyle, T. W., Eds.; Marcel Dekker: New York, 1995.
16. Wenthold, P. G.; Squires, R. R.; Lineberger, W. C. J. Am. Chem. Soc. 1998, 120, 5279.
17. Grützmacher, H. F.; Lohmann, J. Liebigs Ann. Chem. 1970, 733, 88.
18. Grützmacher, H. F.; Lehmann, W. R. Liebigs Ann. Chem. 1975, 2023.
19. Linnert, H. V.; Riveros, J. M. Int. J. Mass Spectrom. Ion Processes 1994, 140, 163.
20. Thoen, K. K.; Kenttämaa, H. I. J. Am. Chem. Soc. 1997, 119, 3832.
21. Thoen, K. K.; Kenttämaa, H. I. J. Am. Chem. Soc. 1999, 121, 800.
22. Diau, E. W. G.; Casanova, J.; Roberts, J. D.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 1376.
23. Chapman, O. L.; Mattes, K.; McIntosh, C. L.; Pacansky, J.; Calder, G. V.; Orr, G. J. Am. Chem. Soc. 1973, 95, 6134.
24. Weimer, H. A.; McFarland, B. J.; Li, S.; Weltner, W. J. Phys. Chem. 1995, 99, 1824.
25. Sander, W.; Bucher, G.; Wandel, H.; Kraka, E.; Cremer, D.; Sheldrick, W. S. J. Am. Chem. Soc. 1997, 119, 10660.
26. Sander, W. Acc. Chem. Res. 1999, 32, 669.
27. Sander, W.; Exner, M. J. Chem. Soc., Perkin Trans. 2 1999, 2285.
28. Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
29. Scheiner, A. C.; Schaefer, H. F., III; Liu, B. J. Am. Chem. Soc. 1989, 111, 3118.
30. Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951.
31. Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958.
32. Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929.
33. Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963.
34. Lindh, R.; Lee, T. J.; Bernhardsson, A.; Persson, B. J.; Karlström, G. J. Am. Chem. Soc. 1995, 117, 7186.
35. Cramer, C. J.; Nash, J. J.; Squires, R. R. Chem. Phys. Lett. 1997, 277, 311.
36. Cramer, C. J.; Squires, R. R. J. Phys. Chem. A 1997, 101, 9191.
37. Kraka, E.; Cremer, D.; Bucher, G.; Wandel, H.; Sander, W. Chem. Phys. Lett. 1997, 268, 313.
38. Lindh, R.; Ryde, U.; Schütz, M. Theor. Chem. Acc. 1997, 97, 203.
39. Chen, W.-C.; Chang, N.-y.; Yu, C.-h. J. Phys. Chem. A 1998, 102, 2584.
40. Lindh, R.; Bernhardsson, A.; Schütz, M. J. Phys. Chem. A 1999, 103, 9913.
41. Galbraith, J. M.; Schreiner, P. R.; Harris, N.; Wei, W.; Wittkopp, A.; Shaik, S. Chem. Eur. J. 2000, 6, 1446.
42. Gräfenstein, J.; Hjerpe, A. M.; Kraka, E.; Cremer, D. J. Phys. Chem. A 2000, 104, 1748.
43. de Visser, S. P.; Filatov, M.; Shaik, S. Phys. Chem. Chem. Phys. 2000, 2, 5046.
44. Bucher, G.; Sander, W.; Kraka, E.; Cremer, D. Angew. Chem., Int. Ed. Engl. 1992, 35, 746.
45. Marquardt, R.; Sander, W.; Kraka, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 746.
46. Davico, G. E.; Schwartz, R. L.; Ramond, T. M.; Lineberger, W. C. J. Am. Chem. Soc. 1999, 121, 6047.
47. Cramer, C. J. J. Chem. Soc., Perkin Trans. 2 1999, 2273.
48. Johnson, W. T. G.; Cramer, C. J. J. Am. Chem. Soc., in press.
49. Ford, G. P.; Biel, E. R. Tetrahedron Lett. 1995, 36, 3663.
50. Schreiner, P. R. J. Am. Chem. Soc. 1998, 120, 4184.
51. Schreiner, P. R. Chem. Commun. 1998, 483.
52. Koseki, S.; Fujimura, Y.; Hirama, M. J. Phys. Chem. A 1999, 103, 7672.
53. Nam, H. H.; Leroi, G. E.; Harrison, J. F. J. Phys. Chem. 1991, 95, 6514.
54. Hoffner, J.; Schottelius, M. J.; Feichtinger, D.; Chen, P. J. Am. Chem. Soc. 1998, 120, 376.
55. Cramer, C. J. J. Am. Chem. Soc. 1998, 120, 6261.
56. Cramer, C. J.; Debbert, S. Chem. Phys. Lett. 1998, 287, 320.
57. Debbert, S. L.; Cramer, C. J. Int. J. Mass Spectrom. 2000, 207, 1.
58. Cramer, C. J.; Squires, R. R. Org. Lett. 1999, 1, 215.
59. Schreiner, P. R.; Prall, M. J. Am. Chem. Soc. 1999, 121, 8615.
60. Andersson, K.; Malmqvist, P.-Å.; Roos, B. O. J. Chem. Phys. 1992, 96, 1218.
61. Chemical Applications of Density Functional Theory; Laird, B. B., Ross, R. B., Ziegler, T., Eds.; ACS Symposium Series 629; American Chemical Society: Washington, DC, 1996.
62. Cizek, J. Adv. Chem. Phys. 1969, 14, 35.
63. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910.
64. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479.
65. Brueckner, K. A. Phys. Rev. 1954, 96, 508.
66. Handy, N.; Pople, J. A.; Head-Gordon, M.; Raghavachari, K.; Trucks, G. W. Chem. Phys. Lett. 1989, 164, 185.
67. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007.
68. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
69. Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B 1996, 54, 16533.
70. Lee, C.; Yang, W.; Pair, R. G. Phys. Rev. B 1988, 37, 785.
71. Gräfenstein, J.; Cremer, D. Phys. Chem. Chem. Phys. 2000, 2, 2091.
72. Gräfenstein, J.; Kraka, E.; Cremer, D. Chem. Phys. Lett. 1998, 288, 593.
73. Sander, W.; Wandel, H.; Bucher, G.; Gräfenstein, J.; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1998, 120, 8480.
74. Stanton, J. F. Chem. Phys. Lett. 1997, 281, 130.
75. Lim, M. H.; Worthington, S. E.; Dulles, F. J.; Cramer, C. J. In Density-Functional Methods in Chemistry; Laird, B. B., Ross, R. B., Ziegler, T., Eds.; ACS Symposium Series 629; American Chemical Society: Washington, DC, 1996; p 402.
76. 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.; Schütz, M.; Seijo, L.; Serrano-Andrés, L.; Siegbahn, P. E. M.; Widmark, P.-O. MOLCAS, Version 4; Lund University: Lund, Sweden, 1997.
77. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; 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.; Peng, C. Y.; Ayala, P. A.; 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 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
78. Ziegler, T.; Rauk, A.; Baerends, E. J. Theor. Chim. Acta 1977, 43, 261.
79. Noodleman, L.; Post, D.; Baerends, E. J. Chem. Phys. 1982, 64, 159.
80. Cramer, C. J.; Dulles, F. J.; Giesen, D. J.; Almlöf, J. Chem. Phys. Lett. 1995, 245, 165.
81. Davidson, E. Int. J. Quantum Chem. 1998, 69, 241.
82. Crawford, T. D.; Stanton, J. F. Preprint.
83. Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
84. Reed, D. R.; Kass, S. R. J. Mass Spectrom. 2000, 35, 534.
85. Cioslowski, J.; Liu, G.; Martinov, M.; Piskorz, P.; Moncrieff, D. J. Am. Chem. Soc. 1996, 118, 5261.
86. Barckholtz, C.; Barckholtz, T. A.; Hadad, C. M. J. Am. Chem. Soc. 1999, 121, 491.
87. Broadus, K. M.; Kass, S. M. To be published.
88. McConnell, H. M. J. Chem. Phys. 1963, 39, 1910.
89. Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179.
90. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259.
91. Yoshizawa, K.; Hoffmann, R. J. Am. Chem. Soc. 1995, 117, 6921.
92. Salem, L. Electrons in Chemical Reactions; John Wiley and Sons: New York, 1982; Chapter 7.
93. Yoshimine, M.; Pacansky, J.; Honjou, N. J. Am. Chem. Soc. 1989, 111, 2785.
94. Hrovat, D. A.; Waali, E. E.; Borden, W. T. J. Am. Chem. Soc. 1992, 114, 8698.
95. Kim, S.-J.; Hamilton, T. P.; Schaefer, H. F., III. J. Am. Chem. Soc. 1992, 114, 5349.
96. Travers, M. J.; Cowles, D. C.; Clifford, E. P.; Ellison, G. B. J. Am. Chem. Soc. 1992, 114, 8699.
97. Sternhell, S. Q. Rev. Chem. Soc. 1969, 23, 236.
98. King, F. W. Chem. Rev. 1976, 76, 157.
99. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds; Chapman and Hall: New York, 1986.
100. Gurvich, L. V.; Veyts, I. V.; Alcock, C. B. Thermodynamic Properties of Individual Substances, 4th ed.; Hemisphere: New York, 1991; Vol. 2, Parts 1 and 2.