CAS MCSCF/CAS MCQDPT2 study of the mechanism of singlet: Oxygen addition to 1,3-butadiene and benzene

Journal of the American Chemical Society

Volumn 122, Issue 34, 2000, Pages 8112-8119

  Bobrowski, Maciej ^a,b   Liwo, Adam ^a   Ołdziej, Stanisław ^a   Jeziorek, Danuta ^c   Ossowski, Tadeusz ^a  

^a UNIVERSITY OF GDA SK   (Poland)

^b GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^c NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; AMPHOLYTE; AROMATIC COMPOUND; BENZENE; OXYGEN; PEROXIDE;

ARTICLE; BINDING AFFINITY; CHEMICAL BOND; CHEMICAL STRUCTURE; OXYGEN AFFINITY; REACTION ANALYSIS;

EID: 0034734369     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001185c     Document Type: Article

References (52)

1. Halliwell, B.; Gutteridge, J. M. C. Free radicals in biology and medicine; Clarendon Press: Oxford, 1985.
2. Kearns, D. R. Chem. Rev. 1971, 71, 395-427.
3. Lissi, E. A.; Encinas, M.; Lemp, E.; Rubio, M. A. Chem. Rev. 1993, 93, 699-723.
4. Pryor, W. A., Ed. Free radicals in biology; Academic Press: New York, 1982; Vol. V.
5. Gérard, M.; Dufraisse, C. C. R. Acad. Sci. 1935, 201, 428-430.
6. Brown, C. J.; Ehrenberg, M. Acta Crystallogr. 1984, C40, 1059-1060.
7. Saito, I.; Kato, S.; Matsuura, T. J. Am. Chem. Soc. 1983, 105, 3200-3206.
8. (a) Saito, I.; Kato, S.; Matsuura, T. Tetrahedron Lett. 1970, 239-242.
9. (b) Kharasch, M. S.; Joshi, B. S. J. Org. Chem. 1957, 22, 1439-1443.
10. (c) Thomas, M. J.; Foote, C. S. Photochem. Photobiol. 1978, 27, 683-693.
11. (d) Clough, R. L.; Yee, B. G.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 683-686.
12. (e) Jensen, F.; Foote, C. S. Photochem. Photobiol. 1987, 46, 325-330.
13. (f) Dowd, P.; Ham, S. W.; Geib, S. J. J. Am. Chem. Soc. 1991, 113, 7734-7743.
14. Bartlett, P. D.; Schaap, A. P. J. Am. Chem. Soc. 1970, 92, 3223-3225.
15. (a) Frimer, A. A. Chem. Rev. 1979, 79, 359-472 and references therein.
16. 2; Frimer, A. A., Ed.; CRC Press Inc.: Boca Raton, FL, 1985; Vol. II, Part 1, Chapter 3, pp 67-91.
17. Jefford, C. W. Chem. Soc. Rev. 1993, 59-66 and references therein.
18. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1975, 97, 3978-3986.
19. Harding, L. B.; Goddard, W. A., III. J. Am. Chem. Soc. 1980, 102, 439-449.
20. Yamaguchi, K.; Yabushita, S.; Fueno, T.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 5043-5046.
21. Hotokka, M.; Roos, B.; Siegbahn, P. J. Am. Chem. Soc. 1983, 105, 5263-5269.
22. Bernardi, F.; Bottoni, A.; Olivucci, M.; Robb, M.; Schlegel, H. B.; Tonachini, G. J. Am. Chem. Soc. 1988, 110, 5993-5995.
23. Tonachini, G.; Schlegel, H. B.; Bernardi, F.; Robb, M. A. J. Am. Chem. Soc. 1990, 112, 483-491.
24. Yoshioka, Y.; Yamada, S.; Kawakami, T.; Nishino, M.; Yamaguchi, K.; Saito, I. Bull. Chem. Soc. Jpn. 1996, 69, 2683-2699.
25. Liwo, A.; Dyl, D.; Jeziorek, D.; Nowacka, M.; Ossowski, T.; Woźnicki, W. J. Comput. Chem. 1997, 18, 1668-1681.
26. Maranzana, A.; Ghigo, G.; Tonachini, G. J. Am. Chem. Soc. 2000, 122, 1414-1423.
27. McCarrick, M. A.; Wu, Y. D.; Houk, K. N. J. Org. Chem. 1993, 58, 3330-3343.
28. Cheikh, F.; Boucekkine, A.; Cartier, A. J. Mol. Struct. THEOCHEM 1997, 397, 13-20.
29. Kondo, T.; Matsumoto, M.; Mitsuoshi, T. Tetrahedron Lett. 1978, 40, 3819-3822.
30. Van den Heuvel, C. J. M.; Hofland, A.; Steinberg, H.; de Boer, T. S. Recl. Trav. Chim. Pays-Bas 1980, 99, 275-278.
31. Clennan, E. L. Tetrahedron 1991, 47, 1343-1382.
32. Gollnick, K.; Griesbeck, A. Tetrahedron Lett. 1983, 24, 3303-3306.
33. Gollnick, K.; Schenck, G. O. In 1,4-Cycloaddition Reactions; Hamer, J., Ed.; Academic Press: Orlando, FL, 1967; pp 255-344.
34. Rigaudy, J.; Capdevielle, P.; Cambrisson, S.; Maumy, M. Tetrahedron Lett. 1974, 2757-2760.
35. Hasty, N. M.; Kearns, D. R. J. Am. Chem. Soc. 1973, 95, 3380-3381.
36. Clennan, E. L.; L'Esperance, R. P. J. Am. Chem. Soc. 1985, 107, 5178-5182.
37. (a) Nakano, H. J. Chem. Phys. 1993, 99, 7983-7992.
38. (b) Nakano, H. Chem. Phys. Lett. 1993, 207, 372-378.
39. Chałasifiski, G.; Kendall, R. A.; Simons, J. J. Chem. Phys. 1987, 87, 2965-2975.
40. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. J.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363.
41. (a) Perales, A.; Martinez-Ripoll, M.; Fayos, J.; Savona, G.; Bruno, M.; Rodriguez, B. J. Org. Chem. 1983, 48, 5318-5371.
42. (b) Zadok, E.; Rubinraut, S.; Frolow, F.; Mazur, Y. J. Org. Chem. 1985, 50, 2647-2649.
43. (c) Sterns, M. J. Cryst. Mol. Struct. 1973, 1, 373-381.
44. (d) Adembri, G.; Celli, A. M.; Donati, D.; Scotton, M.; Sega, A. Acta Crystallogr., Sect. C 1987, 43, 69-71.
45. Allen, F. H.; Kennard, O.; Taylor, R. Acc. Chem. Res. 1983, 16, 146-184.
46. Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 7478-7485.
47. Goldstein, E.; Benno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043.
48. Ashford, R. D.; Ogryzlo, E. A. Can. J. Chem. 1974, 52, 3544-3548.
49. (a) Klein, C. L.; Stevens, E. D.; Zacharias, D. E.; Glusker, J. P. Carcinogenesis 1987, 8, 5-18.
50. (b) Izuoka, A.; Murase, T.; Tsukada, M.; Ito, Y.; Sugawara, T.; Uchida, A.; Sato, N.; Inokuchi, K. Tetrahedron Lett. 1987, 38, 245-248.
51. (c) Sawada, T.; Mimura, K.; Thiemann, T.; Yamato, T.; Tashiro, M.; Mataka, S. J. Chem. Soc., Perkin Trans. I 1998, 1369-1371.
52. Koradi, R.; Billeter, M.; Wüthrich, K. J. Mol. Graphics 1996, 14, 51-55.