Hydrogen atom tunneling in triplet o-methylbenzocycloalkanones: Effects of structure on reaction geometry and excited state configuration

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 6944-6953

  Johnson, Brent A ^a   Kleinman, Mark H ^b   Turro, Nicholas J ^b   Garcia Garibay, Miguel A ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

REACTION CENTERS;

HYDROGEN; OXYGEN; PHOSPHORESCENCE;

ELECTRON TUNNELING;

2 METHYLBENZOCYCLOALKANONE DERIVATIVE; CYCLOALKANONE; HYDROGEN; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEOMETRY; MOLECULAR STABILITY; PHOTOLYSIS; QUANTUM MECHANICS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; X RAY ANALYSIS;

EID: 0037019998     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo016210r     Document Type: Article

References (57)

1. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: New York, 1980.
2. Lee, S.; Hynes, J. T. J. Chim. Phys. Phys.-Chim. Biol. 1996, 1996, 1783-1807
3. (a) Truhlar, D. G.; Liu, Y.-P.; Schenter, G. K.; Garret, B. C. J. Phys. Chem. 1994, 98, 8396-8405.
4. (b) Liu, Y.-P.; Lu, D.; Gonzalez-Lafont, A.; Truhlar, D. G.; Garret, B. C. J. Am. Chem. Soc. 1993, 115, 7806-7817.
5. (a) Zuev, P.; Sheridan, R. S. J. Am. Chem. Soc. 1994, 116, 4123-4124.
6. (b) Chapman, O. L.; Johnson, J. W.; McMahon, R. J.; West, P. R. J. Am. Chem. Soc. 1988, 110, 501-509.
7. (c) Gol'danskii, V. I.; Benderskii, V. A.; Trakhtenberg, L. I. Adv. Chem. Phys. 1993, 75, 349.
8. (a) Kohen, A.; Klinman, J. P. Chem. Biol. 1999, 6, R191-R198.
9. (b) Kohen, A.; Klinman, J. P. Acc. Chem. Res. 1998, 31, 397-404.
10. (c) Rucker, J.; Klinman, J. P. J. Am. Chem. Soc. 1999, 121, 1997-2006.
11. (a) Johnson, B. A.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1999, 121, 8114-8115.
12. (b) Garcia-Garibay, M. A.; Gamarnik, A.; Pang, L.; Jenks, W. S. J. Am. Chem. Soc. 1994, 116, 12095-12096.
13. (c) Garcia-Garibay, M. A.; Gamarnik, A.; Bise, R.; Jenks, W. S. J. Am. Chem. Soc. 1995, 117, 10264-10275.
14. (d) Johnson, B.; Gamarnik, A.; Garcia-Garibay, M. A. J. Phys. Chem. 1996, 100, 4697-4700.
15. (e) Gamarnik, A.; Johnson, B. A.; Garcia-Garibay, M. A. J. Phys. Chem., 1998, 102, 5491-5498.
16. (a) Al-Soufi, W.; Eychmuller, A.; Grellmann, K. H. J. Phys. Chem. 1991, 95, 2022-2026.
17. (b) Smedarchina, Z.; Enchev, V.; Lavtchieva, L. J. Phys. Chem. 1994, 98, 4218-29.
18. A similar hydrogen atom tunneling reaction has been observed in radical ions of analogous compounds: (a) Bednarek, P.; Zhu, Z.; Bally, T.; Filipiak, T.; Marcinek, A.; Gebicki, J. J. Am. Chem. Soc. 2001, 123, 2377-2387. (b) Marcinek, A.; Adamus, J.; Huben, K.; Gebicki, J.; Bartczak, T. J.; Bednarek, P.; Bally, T. J. Am. Chem. Soc. 2000, 122, 437-443.
19. A similar hydrogen atom tunneling reaction has been observed in radical ions of analogous compounds: (a) Bednarek, P.; Zhu, Z.; Bally, T.; Filipiak, T.; Marcinek, A.; Gebicki, J. J. Am. Chem. Soc. 2001, 123, 2377-2387. (b) Marcinek, A.; Adamus, J.; Huben, K.; Gebicki, J.; Bartczak, T. J.; Bednarek, P.; Bally, T. J. Am. Chem. Soc. 2000, 122, 437-443.
20. Turro, N. J.; Gould, I. R.; Liu, J.; Jenks, W. S.; Staab, H.; Alt, R. J. Am. Chem. Soc. 1989, 111, 6378-83.
21. Turro, N. J. Modern Molecular Photochemistry; Benjamin Cummings Publishing Co.: Menlo Park, CA, 1978.
22. Berger, M.; McAlpine, E.; Steel, C. J. Am. Chem. Soc. 1978, 100, 5147-51.
23. Wagner, P. J.; Kemppainen, A. E.; Schott, H. N. J. Am. Chem. Soc. 1973, 95, 5604-5614.
24. (a) Yang, N. C.; McClure, D. S.; Murov, S. L.; Houser, J. J.; Dusenbury, R. J. Am. Chem. Soc. 1967, 89, 5466-5468.
25. (b) Case, W. A. J. Chem. Phys. 1970, 52, 2175-2191.
26. (c) Case, W. A.; Kearns, D. R. J. Chem. Phys. 1970, 52, 2175-2191.
27. (a) Johnson, B. A.; Hu, Y.; Houk, K. N.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2001, 123, 6941-6942.
28. (b) Johnson, B. A. Ph.D. Thesis, University of California, Los Angeles, CA, 1999.
29. A detailed derivation of eq 3 is also available in the Supporting Information section of ref 6a.
30. (a) Khalaf, A. A.; Abdel-Wahab, A.-M. A.; El-Khawaga, A. M.; El-Zohry, M. F. Bull. Soc. Chim. Fr. 1984, 1984, 285-291.
31. (b) Bergmark, W. R.; Barnes, C.; Clark, J.; Paparian, S.; Marynowski, S. J. Org. Chem. 1985, 50, 5612-5615.
32. Fisnerova, L.; Kakac, B.; Nemecek, O.; Simek, A.; Vejdelek, Z. J. Collect. Czech. Chem. Commun. 1967, 32, 4082-4098.
33. Brugidou, J.; Christol, H.; Sachetto, J. P. Bull. Soc. Chim. Fr. 1967, 7, 2579-2584.
34. McGarry, P. F.; Cheh, J.; Ruiz-Silva, B.; Hu, S.; Wang, J.; Nakanishi, K.; Turro, N. J. J. Phys. Chem. 1996, 100, 646-654.
35. Wagner, P. J.; Chen, C.-P. J. Am. Chem. Soc. 1976, 98, 239-241.
36. Akiyama, K.; Ikegami, Y.; Tero-Kubota, S. J. Am. Chem. Soc. 1987, 109, 2538-2539.
37. Das, P. K.; Encinas, M. V.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1979, 101, 6965-6970.
38. -1).
39. Baron, U.; Bartlet, G.; Eychmuller, A.; Grellman, K.-H.; Schmitt, U.; Tauer, E.; Weller, H. J. Photochem. 1985, 28, 187-195.
40. Migirdicyan, E.; Baudet, J. J. Am. Chem. Soc. 1975, 97, 7400-7404.
41. Flynn, C. R.; Michl, J. J. Am. Chem. Soc. 1974, 96, 3280-3288.
42. (a) Lutz, H.; Lindqvist, L. Chem. Commun. 1971, 493-494.
43. (b) Lutz, H.; Bréhéret, E.; Lindqvist, L. J. Phys. Chem. 1973, 1758-1762.
44. Khalaf, A. A.; Abdel-Wahab, A.-M.; El-Khawaga, A. M.; ElZohry, M. F. Bull. Soc. Chim. Fr., 1984, 258-291.
45. Michl, J.; Bonacic-Koutecky, V. Electronic Aspects of Organic Photochemistry; Wiley-Interscience: New York, 1990.
46. Salem, L. Science 1976, 191, 822-30.
47. Dauben, W. G.; Salem, L.; Turro, N. J. Acc. Chem. Res. 1975, 8, 41-54.
48. Wagner, P. J. Acc. Chem. Res. 1983, 16, 461-467.
49. Lewis, F. D.; Johnson, R. W.; Johnson, D. E. J. Am. Chem. Soc. 1974, 96, 6090-6099.
50. Gudmundsdottir, A. D.; Lewis, T. J.; Randall, L. H.; Scheffer, J. R.; Rettig, S. J.; Trotter, J.; Wu, C.-H. J. Am. Chem. Soc. 1996, 118, 6167-6184.
51. Scheffer, J. R.; Dzakpasu, A. J. Am. Chem. Soc. 1978, 100, 2163-73.
52. (a) Scheffer, J. R.; Garcia-Garibay, M. A.; Nalamasu, O. Org. Photochem. 1987, 8, 249-347.
53. (b) Scheffer, J. R. Solid State Organic Chemistry; Desiraju, G. R., Ed.; VCH: Amsterdam, The Netherlands, 1987; pp 1-45.
54. (a) Dorigo, A. E.; McCarrick, M. A.; Loncharich, R. J.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 7508-7514.
55. (b) Dorigo, A. N.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 2195-2197.
56. (a) Sreedhara Rao, V.; Chandra, A. K. Chem. Phys. 1997, 214, 103-112.
57. (b) Chandra, A. K.; Sreedhara Rao, V. Chem. Phys. Lett. 1998, 270, 87-92