Spontaneous Hydrogen Atom Transfer on Ionization: Characterization of Enol Radical Cations in Cryogenic Matrices

Accounts of Chemical Research

Volumn 30, Issue 12, 1997, Pages 477-485

  Gebicki, Jerzy ^a,c,d,e,f   Bally, Thomas ^b,g,h  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF FRIBOURG   (Switzerland)

^c STONY BROOK UNIVERSITY   (United States)

^d UNIVERSITY OF UTAH   (United States)

^e TUL   (Poland)

^f Institute of Applied Radiation Chemistry   (Poland)

^g UNIVERSITY OF BASEL   (Switzerland)

^h MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001354998     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar960094a     Document Type: Article

References (58)

1. (a) Radical Ionic Systems; Lund, A., Shiotoni, M., Eds.; Kluwer: Dordrecht, The Netherlands, 1991.
2. (b) Shida, T. Ann. Rev. Phys. Chem. 1991, 42, 55.
3. (c) Roth, H. D. Top. Curr. Chem. 1992, 163, 131.
4. (d) Gerson, F. Acc. Chem. Res. 1994, 27, 63.
5. (e) Gebicki, J. Pure Appl. Chem. 1995, 67, 55.
6. (f) Dass, C. Mass Spectrom. Rev. 1990, 9, 1.
7. (a) Schwarz, H. Adv. Mass Spectrom. 1985, 10A, 13.
8. (b) Bouchoux, E. Mass Spectrosc. Rev. 1988, 7, 1, 203.
9. (c) Hammerum, S. Ibid. 1988, 7, 123.
10. (a) Iwasaki, M.; Muto, H.; Toriyama, K. Nunome, K. Chem. Phys. Lett. 1984, 105, 586, 592.
11. (b) Sevilla, M. D.; Becker, D.; Sevilla, C. L.; Swarts, S. J. Phys. Chem. 1984, 88, 1701.
12. (c) Rideout, J.; Symons, M. C. R.; J. Chem. Soc., Perkin Trans. 2 1986, 625.
13. (a) The Chemistry of Enols; Rappoport, Z., Ed.; Wiley: Chlchester, U.K., 1990.
14. (b) Toullec, J. In ref 4a, pp 323-398.
15. (c) Turecek, F. In ref 4a, pp 95-146.
16. (a) Schmittel, M. Top. Curr. Chem. 1994, 169, 183.
17. (b) Schmittel, M.; Gescheidt, E.; Röck, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1961.
18. Bally, T. In ref 1a, pp 3-54.
19. Molecular Ions: Spectroscopy, Structure and Chemistry, Miller, T. A., Bondybey, V. E., Eds.; North-Holland: Amsterdam, 1983; Chapters 5 and 6.
20. (a) Shida, T.; Haselbach, E.; Bally, T. Acc. Chem. Res. 1984, 17, 180.
21. (b) Iwamura, H.; Eaton, D. F. Pure Appl. Chem. 1991, 63, 1003.
22. (c) Shida, T.; Electronic Absorption Spectra of Radical Ions; Elsevier: Amsterdam, 1988.
23. Bos, J.; Schmidt, J.; Mai, H.; Decker, V.; Halbing, M. Radiat. Phys. Chem. 1989, 34, 361.
24. (a) Mehnert, R. In ref 1a, pp 231-285.
25. (b) Trifunac, A. D.; Werst, D. W. In ref 1a, pp 195-229.
26. (c) Werst, D. W.; Trifunac, A. D. J. Phys. Chem. 1991, 95, 3466.
27. (a) Gebicki, J. L.; Gebicki, J.; Mayer, J. Radiat. Phys. Chem. 1987, 30, 165.
28. (b) Gebicki, J.; Marcinek, A.; Mayer, J. J. Am. Chem. Soc. 1989, 111, 3098.
29. (a) Gebicki, J.; Marcinek, A.; Stradowski, C. J. Phys. Org. Chem. 1990, 3, 606.
30. (b) Marcinek, A.; Gebicki, J.; Plonka, A. Ibid. 1990, 3, 757.
31. (c) Rogowski, J.; Adamus, J.; Gebicki, J.; Nelsen, S. F. J. Chem. Soc., Perkin Trans. 2, 1994, 779.
32. (d) Marcinek, A.; Rogowski, J.; Adamus, J.; Gebicki, J.; Platz, M. S. J. Phys. Chem. 1996, 100, 13539.
33. (a) Ishiguro, K.; Khudaykov, I. V.; McGarry, P. F.; Turro, N. J.; Roth, H. D. J. Am. Chem. Soc. 1994, 116, 6933.
34. (b) Trifunac, A. D.; Werst, D. W.; Herges, R.; Neumann, H.; Prinzbach, H.; Etzkom, M. Ibid. 1996, 118, 9444.
35. (a) Sammes, P. G. Tetrahedron, 1976, 32, 405.
36. (b) Haag, R; Wirz, J.; Wagner, P. J. Helv. Chim. Acta 1977, 60, 2595.
37. (c) Scaiano, J. C. Acc. Chem. Res. 1982, 15, 252.
38. (d) Wagner, P. J. Acc. Chem. Res. 1989, 22, 83.
39. (e) Weedon, A. C. In ref 2, pp 591-638.
40. This can be seen readily if one compares the hydrogenation enthalpy of benzene giving 1,3-cyclohexadiene (+5.6 kcal/mol) to that of the corresponding radical cation (-17.4 kcal/mol). The difference between the two numbers is close to the ca. 20 kcal/mol which is customarily associated with the extra resonance energy of benzene, which is lost on removing an electron from the 6π cyclic system.
41. Gebicki, I.; Marcinek, A.; Michalak, J.; Rogowski, J.; Bally, T.; Tang, W. J. Mol. Struct 1992, 275, 249.
42. Marcinek, A.; Michalak, I.; Rogowski, J.; Tang, W.; Bally, T.; Gebicki, J. J. Chem. Soc., Perkin Trans. 2 1992, 1353.
43. Tang, W.; Bally, T. Unpublished results.
44. Kesper, K.; Münzel, N.; Pietzuch, W.; Specht, H.; Schweig, A. J. Mol. Struct. (THEOCHEM) 1989, 200, 375.
45. (a) Michalak, J.; Jonska, A.; Tang, W.; Gebicki, J. Polish J. Chem. 1993, 67, 1505.
46. (b) Michalak, J. W.; Gebicki, J. J. Chem. Soc., Perkin Trans 2, 1993, 2249.
47. See, e.g.: Plonka, A. In Time-Dependent Reactivity of Species in Condensed Media; Lecture Notes in Chemistry, Vol. 40; Springer: Heidelberg, Germany, 1986.
48. See: Caldin, E. F. Chem. Rev. 1969, 69, 135.
49. Grellmann, K. H.; Welter, H.; Tauer, E. Chem. Phys. Lett. 1983, 95, 195.
50. Michalak, J.; Bally, T.; Gebicki, J. Pol. J. Chem. 1993, 67, 1403.
51. Michalak, J.; Bally, T. Unpublished results.
52. Bally, T.; Michalak, J. J. Photochem. Photobiol. A: Chem. 1992, 69, 185.
53. Huben, K.; Zhu, Z.; Bally, T.; Filipiak, T.; Gebicki, J. To be published.
54. Michalak, J.; Gebicki, I.; Bally, T. J. Chem. Soc., Perkin Trans. 2 1993, 1321.
55. Huben, K.; Zhu, Z.; Bally, T.; Gebicki, J. J. Am. Chem. Soc. 1997, 119, 2825.
56. Michalak, J.; Bally, T.; Gebicki, J. Radiat. Phys. Chem. 1995, 45, 749
57. Gebicki, J.; Marcinek, A.; Adamus, J.; Paneth, P.; Rogowski, J. J. Am. Chem. Soc. 1996, 118, 691
58. Gauld, J. W.; Audier, H.; Fossey, J.; Radom, L. J. Am. Chem. Soc. 1996, 118, 6299.