The para-Didehydropyridine, para-Didehydropyridinium, and Related Biradicals - A Contribution to the Chemistry of Enediyne Antitumor Drugs

Journal of Computational Chemistry

Volumn 22, Issue 2, 2001, Pages 216-229

  Kraka, Elfi ^a   Cremer, Dieter ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

Bergman cyclization; DFT on top pair density; Para didehydrobenzene; Para didehydroheterobenzenes; S T splitting

Indexed keywords

EID: 0000189172     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/1096-987x(20010130)22:2<216::aid-jcc9>3.0.co;2-x     Document Type: Article

References (70)

1. For reviews see (a) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995; (b) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497; (c) Nicolaou, K. C.; Dai, W.-M. Angew Chem Int Ed Engl 1991, 30,1387; (d) Pogozelski, W. K.; Tullius, T. D. Chem Rev 1998, 98, 1089; (e) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1; (f) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorgan Chem 1999, 27, 172; (g) Wisniewski Grimssom, J.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453; (h) Fallis, A. G. Can J Chem 1999, 77, 159.
2. For reviews see (a) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995; (b) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497; (c) Nicolaou, K. C.; Dai, W.-M. Angew Chem Int Ed Engl 1991, 30,1387; (d) Pogozelski, W. K.; Tullius, T. D. Chem Rev 1998, 98, 1089; (e) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1; (f) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorgan Chem 1999, 27, 172; (g) Wisniewski Grimssom, J.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453; (h) Fallis, A. G. Can J Chem 1999, 77, 159.
3. For reviews see (a) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995; (b) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497; (c) Nicolaou, K. C.; Dai, W.-M. Angew Chem Int Ed Engl 1991, 30,1387; (d) Pogozelski, W. K.; Tullius, T. D. Chem Rev 1998, 98, 1089; (e) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1; (f) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorgan Chem 1999, 27, 172; (g) Wisniewski Grimssom, J.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453; (h) Fallis, A. G. Can J Chem 1999, 77, 159.
4. For reviews see (a) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995; (b) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497; (c) Nicolaou, K. C.; Dai, W.-M. Angew Chem Int Ed Engl 1991, 30,1387; (d) Pogozelski, W. K.; Tullius, T. D. Chem Rev 1998, 98, 1089; (e) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1; (f) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorgan Chem 1999, 27, 172; (g) Wisniewski Grimssom, J.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453; (h) Fallis, A. G. Can J Chem 1999, 77, 159.
5. For reviews see (a) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995; (b) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497; (c) Nicolaou, K. C.; Dai, W.-M. Angew Chem Int Ed Engl 1991, 30,1387; (d) Pogozelski, W. K.; Tullius, T. D. Chem Rev 1998, 98, 1089; (e) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1; (f) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorgan Chem 1999, 27, 172; (g) Wisniewski Grimssom, J.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453; (h) Fallis, A. G. Can J Chem 1999, 77, 159.
6. For reviews see (a) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995; (b) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497; (c) Nicolaou, K. C.; Dai, W.-M. Angew Chem Int Ed Engl 1991, 30,1387; (d) Pogozelski, W. K.; Tullius, T. D. Chem Rev 1998, 98, 1089; (e) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1; (f) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorgan Chem 1999, 27, 172; (g) Wisniewski Grimssom, J.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453; (h) Fallis, A. G. Can J Chem 1999, 77, 159.
7. For reviews see (a) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995; (b) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497; (c) Nicolaou, K. C.; Dai, W.-M. Angew Chem Int Ed Engl 1991, 30,1387; (d) Pogozelski, W. K.; Tullius, T. D. Chem Rev 1998, 98, 1089; (e) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1; (f) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorgan Chem 1999, 27, 172; (g) Wisniewski Grimssom, J.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453; (h) Fallis, A. G. Can J Chem 1999, 77, 159.
8. For reviews see (a) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995; (b) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497; (c) Nicolaou, K. C.; Dai, W.-M. Angew Chem Int Ed Engl 1991, 30,1387; (d) Pogozelski, W. K.; Tullius, T. D. Chem Rev 1998, 98, 1089; (e) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1; (f) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorgan Chem 1999, 27, 172; (g) Wisniewski Grimssom, J.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453; (h) Fallis, A. G. Can J Chem 1999, 77, 159.
9. (a) Jones, R. R.; Bergman, R. G. J Am Chem Soc 1972, 94, 660;
10. (b) Bergman, R. G. Acc Chem Res 1973, 6, 25;
11. (c) Lockhart, T. P.; Comita, P. B.; Bergman, R. G. J Am Chem Soc 1981, 103, 4082;
12. (d) Lockhart, T. P.; Bergman, R. G. J Am Chem Soc 1981, 103, 4091;
13. (e) Gleiter, R.; Kratz, D. Angew Chem Int Ed Engl 1993, 32, 842;
14. (f) Turro, N. J.; Evenzahav, A.; Nicolaou, K. C. Tetrahedron Lett 1994, 35, 8089;
15. (g) Kuwatani, Y; Ueda, I. Angew Chem Int Ed Engl 1995, 34, 1892.
16. See, for example, Casazza, A. M.; Kelly, S. L. In Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995, p. 283.
17. (a) Tannock, I. F.; Rotin, D. Cancer Res 1989, 49, 4373;
18. (b) Sevick, E. M.; Jain, R. K. Cancer Res 1988, 48, 1201.
19. Hoffner, J. H.; Schottelius, M. J.; Feichtinger, D.; Chen, P. J Am Chem Soc 1998, 120, 376.
20. Marquardt, R., Balster, A.; Sander, W.; Kraka, E.; Cremer, D.; Radziszewiski, J. G. Angew Chem 1998, 110, 1001.
21. (a) David, W. M.; Kervin, S. M. J Am Chem Soc 1997, 119, 1464;
22. (b) Chen, P. private communication.
23. Kraka, E.; Cremer, D. J Am Chem Soc 1994, 116, 4929.
24. Koga, N.; Morokuma, K. J Am Chem Soc 1991, 113, 1907.
25. (a) Wenthold, P. G.; Paulino, J. A.; Squires, R. R. J Am Chem Soc 1991, 113, 7414;
26. (b) Wenthold, P. G.; Squires, R. R. J Am Chem Soc 1994, 116, 6401;
27. (c) Wierschke, S. G.; Nash, J. J. Squires, R. R. J Am Chem Soc 1993, 115, 11958.
28. (a) Lindh, R.; Persson, B. J. J Am Chem Soc 1994, 116, 4963;
29. (b) Lindh, R.; Lee, T. J.; Berhardsson, A.; Persson, B. J.; Karlstrm, G. J Am Chem Soc 1995, 117, 7186.
30. (a) Cramer, C. J.; Nash, J. J.; Squires, R. R. Chem Phys Lett 1997, 277, 311;
31. (b) Cramer, C. J.; Debbert, S. Chem Phys Lett 1998, 287, 320;
32. (c) Cramer, C. J. J Am Chem Soc 1998, 120, 6261;
33. (d) Cramer, C. J.; Squires, R. R. Organic Lett 1999, 1, 215.
34. Chen, W.-C.; Chang, N.-Y.; Yu, C.-H. J Phys Chem A 1998, 102, 2484.
35. (a) Schreiner, P. R. J Am Chem Soc 1998, 120, 4184;
36. (b) Schreiner, P. R. Chem Commun 1998, 483;
37. (c) Schreiner, P. R.; Prall, M. J Am Chem Soc 1999, 121, 8615.
38. Hoffmann, R.; Imamura, A.; Hehre, W. J. J Am Chem Soc 1968, 90, 1499.
39. Roth, W. R.; Hopf, H.; Horn, C. Chem Ber 1994, 127, 1765.
40. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem Phys Lett 1989, 157, 479.
41. Handy, N. C.; Pople, J. A.; Head-Gordon, M.; Raghavachari, K.; Trucks, G. W. Chem Phys Lett 1989, 164, 185.
42. (a) Roos, B. O. In Advances in Chemistry & Physics, Vol. 69, Ab Initio Methods in Quantum Chemistry II; Lawley, K. P., Ed.; Wiley: New York, 1987, p. 447;
43. (b) Andersson, K.; Malmqvist, P.-A.; Roos, B. O.; Sadlej, A. J.; Wolinski, K. J Phys Chem 1990, 94, 5483;
44. (c) Andersson, K.; Malmqvist, P.-A.; Roos, B. O. J Phys Chem 1992, 96, 1218.
45. Gräfenstein, J.; Hjerpe, A. M.; Kraka, E.; Cremer, D. J Phys Chem 2000, 104, 1748.
46. Gräfenstein, J.; Cremer, D. to appear.
47. Noodleman, L.; Post, D.; Baerends, E. J. Chem Phys 1982, 64, 159.
48. (a) Ziegler, T.; Rauk, A.; Baerends, E. J. Theor Chim Acta 1977, 43, 261;
49. (b) Noodleman, L.; Case, D. A. Adv Inorg Chem 1992, 38, 423;
50. (c) Lovell, T.; McGrady, J. E.; Stranger, R.; MacGregor, S. Inorg Chem 1996, 35, 3079;
51. (d) Ziegler, T.; Rauk, A.; Baerends, E. J. Theor Chim Acta 1997, 43, 261;
52. (e) Cramer, C. J.; Dulles, F. J.; Giesen, D. J.; Almöff, J. Chem Phys Lett 1995, 245, 165.
53. Perdew, J. P.; Savin, A.; Burke, K. Phys Rev A 1995, 51, 4531.
54. (a) Becke, A. D. J Chem Phys 1993, 98, 5648.
55. See also (b) Stevens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J Phys Chem 1994, 98, 11623;
56. (c) Becke, A. D. Phys Rev 1988, A38, 3098.
57. (a) See ref. 25;
58. (b) Lee, C.; Yang, W.; Parr, R. G. Phys Rev 1988, B37, 785;
59. Wenthold, P. G.; Squires, R. R.; Lineberger, W. C. J Am Chem Soc 1998, 120, 5279.
60. Hariharan, P. C.; Pople, J. A. Theor Chim Acta 1973, 28, 213.
61. Krishnan, R.; Frisch, M.; Pople, J. A. Chem Phys 1980, 72, 4244.
62. Becke, A. D. J Chem Phys 1988, 88, 2547.
63. Kraka, E.; Gräfenstein, J.; Gauss, J.; Reichel, F.; Olsson, L.; Konkoli, Z.; He, Z.; Cremer, D. COLOGNE 99; Göteborg University: Göteborg, 1999.
64. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, 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.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S. Pople, J. A. Gaussian 98, Revision A.3; Gaussian, Inc.: Pittsburgh, PA, 1998.
65. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity, Electronic and Structural Aspects; Wiley: New York, 1994.
66. Kraka, E.; Cremer, D. J Mol Struct (Theochem) 2000, 506, 191.
67. Kraka, E.; Cremer, D. J Am Chem Soc 2000, 122, 8245.
68. (a) Zabicky, J., Ed. The Chemistry of Functional Groups, The Chemistry of Amides; Wiley: New York, 1970;
69. (b) Homer, R. B.; Johnson, C. D. In Zabicky, J., Ed. The Chemistry of Functional Groups, The Chemistry of Amides; Wiley: New York, 1970, Chapt. 3.
70. Patai, S.; Rappoport, Z., Eds. The Chemistry of Functional Groups, The Chemistry of Amidines and Imidates; Wiley: New York, 1991; vol. 2.