The radical cation of syn-tricyclooctadiene and its rearrangement products

Chemistry - A European Journal

Volumn 6, Issue 5, 2000, Pages 858-868

  Bally, Thomas ^a   Bernhard, Stefan ^a,e   Matzinger, Stephan ^a   Roulin, Jean Luc ^a   Narahari Sastry, G ^a   Truttmann, Leo ^a   Zhu, Zhendong ^a   Marcinek, Andrzej ^b   Adamus, Jan ^b   Kaminski, Rafal ^b,f   Gebicki, Jerzy ^b   Williams, Ffrancon ^c   Chen, Guo Fei ^c   Fülscher, Markus P ^d  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^c UNIVERSITY OF TENNESSEE   (United States)

^d CHEMICAL CENTER   (Sweden)

^e Department of Obstetrics Gynecology   (United States)

^f POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

Electronic structure; Radical ions; Rearrangements; Spectroscopy; Theoretical calculations

Indexed keywords

ALKADIENE; BICYCLO[4.2.0]OCTA 2,4,7 TRIENE; RADICAL; TRICYCLO[4.2.0.0 2.5]OCTA 3,7 DIENE; UNCLASSIFIED DRUG;

ARTICLE; CATION EXCHANGE; DIMERIZATION; DRUG SYNTHESIS; LIGAND BINDING; PHOTOCHEMISTRY; REACTION ANALYSIS; SPECTROSCOPY;

EID: 0034599009     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000303)6:5<858::AID-CHEM858>3.0.CO;2-T     Document Type: Article

References (58)

1. K. Hassenrück, H.-D. Martin, R. Walsh, Chem. Rev. 1989, 89, 1125.
2. S. Dai, J. T. Wang, F. Williams, J. Am. Chem. Soc. 1990, 112, 2835, 2837.
3. T. Bally, L. Truttmann, S. Dai, J. T. Wang, F. Williams, Chem. Phys. Lett. 1993, 212, 141.
4. T. Bally, L. Truttmann, S. Dai, F. Williams, J. Am. Chem. Soc. 1995, 117, 7916.
5. T. Bally, L. Truttmann, J. T. Wang, F. Williams, J. Am. Chem. Soc. 1995, 117, 7923.
6. T. Bally, S. Bernhard, S. Matzinger, L. Truttmann, Z. Zhu, J.-L. Roulin, A. Marcinek, J. Gebicki, F. Williams, G.-F. Chen, H. D. Roth, T. Herbertz, Chem. Eur. J. 2000, 6, 849.
7. R. Gleiter, Top. Curr. Chem. 1979, 86, 197.
8. A. Plonka, Annu. Rep. Prog. Chem. 1989, 85, 47.
9. A. Marcinek, J. Gebicki, A. Plonka, J. Phys. Org. Chem. 1990, 3, 757.
10. T. Bally, K. Roth, R. Straub, Helv. Chim. Acta 1989, 72, 73.
11. T. Bally, S. Nitsche, K. Roth, E. Haselbach, J. Am. Chem. Soc. 1984, 106, 3927.
12. G. Bieri, F. Burger, E. Heilbronner, J. P. Maier, Helv. Chim. Acta 1977, 60, 2213.
13. S. Dai, J. T. Wang, F. Williams, J. Am. Chem. Soc. 1990, 112, 2835.
14. S. Dai, J. T. Wang, F. Williams, J. Am. Chem. Soc. 1990, 112, 2837.
15. R. Gleiter, E. Heilbronner, M. Hekman, H. D. Martin, Chem. Ber. 1973, 106, 28.
16. N. Bodor, B. H. Chen, S. D. Worley, J. Electron Spectrosc. Relat. Phenom. 1974, 4, 65.
17. G. Wipff, PhD thesis, Université Louis Pasteur, Strasbourg, 1971.
18. J. Spanget-Larsen, R. Gleiter, L. A. Paquette, M. J. Carmody, C. R. Degenhardt, Theor. Chim. Acta 1978, 50, 145.
19. 1(π) state was first carried out at the CASSCF level. At the resulting minimum, this state was the ground state and could be reoptimized by the B3LYP method.
20. This is rather surprising in view of the known reluctance of DFT to localize spin and charge (or to overstabilize delocalized states). T. Bally, G. N. Sastry, J. Phys. Chem. A. 1997, 101, 7923.
21. Y. K. Zhang, W. T. Yang, J. Chem. Phys. 1998, 109, 2604.
22. T. A. Halgren, W. N. Lipscomb, Chem. Phys. Lett. 1977, 49, 225.
23. B. Badger, B. Brocklehurst, Trans. Farad. Soc. 1970, 66, 2939.
24. B. Badger, B. Brocklehurst, Trans. Farad. Soc. 1969, 65, 2576, 2582, 2588.
25. G. A. Olah, J. S. Staral, R. J. Spear, G. Liang, J. Am. Chem. Soc. 1975, 97, 5489.
26. S. Sieber, P. von R. Schleyer, A. H. Otto, J. Gauss, F. Reichel, D. Cremer, J. Phys. Org. Chem. 1993, 6, 445.
27. G. E. Gream, L. R. Smith, J. Meinwald, J. Org. Chem. 1974, 39, 3461.
28. L. R. Smith, G. E. Gream, J. Meinwald, J. Org. Chem. 1977, 42, 927.
29. See e. g.: G. N. Sastry, T. Bally, V. Hrouda, P. Carsky, J. Am. Chem. Soc. 1998, 120, 9323.
30. T. Bally, W. T. Borden in Rev. Comput. Chem., Vol. 13 (Eds.: K. B. Lipkowitz, D. B. Boyd), WILEY-VCH, New York, 1999, pp. 1.
31. F. Williams, Acc. Chem. Res. 1999, to be submitted.
32. I. B. Bersuker, Electronic Structure and Properties of Transition Metal Compounds, Wiley, New York, 1996.
33. 1).
34. See, e. g.: H. Köppel, L. S. Cederbaum, W. Domcke, S. S. Shaik, Angew. Chem. 1983, 95, 211; Angew. Chem. Int. Ed. Engl. 1983, 22, 210.
35. See, e. g.: H. Köppel, L. S. Cederbaum, W. Domcke, S. S. Shaik, Angew. Chem. 1983, 95, 211; Angew. Chem. Int. Ed. Engl. 1983, 22, 210.
36. M. Avram, I. G. Dinulescu, E. Marcia, G. Meteescu, E. Sliam, C. D. Nenitzescu, Chem. Ber. 1964, 97, 382.
37. C. Sandorfy, Can. J. Spectrosc. 1965, 85, 10.
38. A. Grimison, G. A. Simpson, J. Phys. Chem. 1968, 72, 1776.
39. T. Bally in Radical Ionic Systems, Vol. 6 (Eds.: A. Lund, M. Shiotani), Kluwer, Dordrecht, 1991, pp. 3-54.
40. S. Karolczak, K. Hodyr, R. Lubis, J. Kroh, Radioanal. Nucl. Chem. 1986, 101, 177.
41. R. Dressler, L. Neuhaus, M. Allan, J. Electron Spectrosc. Relat. Phenom. 1983, 31, 181.
42. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
43. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
44. B. G. Johnson, P. M. W. Gill, J. A. Pople, J. Chem. Phys. 1993, 98, 5612.
45. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montogomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Repogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. DeFrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, M. C. Gonzales, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
46. C. Gonzales, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154.
47. Coupled-cluster method with single and double excitations supplemented by a non-iterative estimation of the contributions of triple excitations, based on a spin-restricted HF zero-order wavefunction. P. J. Knowles, C. Hampel, H.-J. Werner, J. Chem. Phys. 1993, 99, 5219.
48. D. E. Woon, T. H. Dunning, J. Chem. Phys. 1993, 98, 1358.
49. J.-J. Werner, P. J. Knowles, J. Almlöf, R. D. Amos, M. J. O. Deegan, S. T. Elbert, C. Hampel, W. Meyer, K. Peterson, R. Pitzer, A. J. Stone, P. R. Taylor, R. Lindh, 1996.
50. K. Andersson, B. O. Roos in Modern Electronic Structure Theory, Part 1, Vol. 2, World Scientific Publ. Co., Singapore, 1995, pp. 55.
51. K. Andersson, M. R. A. Blomberg, M. P. Fülscher, V. Kellö, R. Lindh, P.-A. Malmqvist, J. Noga, J. Olson, B. O. Roos, A. Sadlej, P. E. M. Siegbahn, M. Urban, P.-O. Widmark, MOLCAS 4, University of Lund, Sweden, 1994.
52. M. P. Fülscher, S. Matzinger, T. Bally, Chem. Phys. Lett. 1995, 236, 167.
53. Z. Zhu, T. Bally, J. Wirz, M. Fülscher, J. Chem. Soc. Perkin Trans. 2 1998, 1083.
54. T. Bally, C. Carra, M. P. Fülscher, Z. Zhu, J. Chem. Soc. Perkin Trans. 2 1998, 1759.
55. P.-O. Widmark, P.-A. Malmqvist, B. O. Roos, Theor. Chim. Acta 1990, 77, 291.
56. T. Bally, B. Albrecht, S. Matzinger, M. G. Sastry, MOPLOT 3.2, University of Fribourg, 1997.
57. E. Haselbach, A. Schmelzer, Helv. Chim. Acta 1979, 54, 1299.
58. In the distributed version of Gaussian 98, only the coupling between the ground state and the first excited state can be evaluated. Slight modifications of the program were necessary to extend this capability to encompass higher excited states. We wish to thank Prof. Michael Robb for guiding us in implementing these changes.