Electron Transfer from Aromatic Hydrocarbons and Their π-Complexes with Metals. Comparison of the Standard Oxidation Potentials and Vertical Ionization Potentials

Journal of the American Chemical Society

Volumn 106, Issue 14, 1984, Pages 3968-3976

  Howell, J O ^a   Goncalves, J M ^a   Klasinc, L ^a   Wightman, R M ^a   Amatore, C ^b   Kochi, J K ^b  

^a INDIANA UNIVERSITY   (United States)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRODES; HYDROCARBONS;

BENZENE;

EID: 0021456218     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00326a014     Document Type: Article

References (79)

1. Lowry, T. H.; Richardson, K. S. “Mechanism and Theory in Organic Chemistry”, 2nd ed.; Harper and Row: New York, 1981.
2. Beletskaya, I. P.; Makhon'kov, D. I. Russ. Chem. Rev. (Engl. Transl.) 1981, 50, 1007.
3. Chanon, M.; Tobe, M. L. Angew. Chem., Int. Ed. Engl. 1982, 21, 1.
4. Chanon, M. Bull. Soc. Chim. Fr. 1982, 11-197.
5. Julliard, M.; Chanon, M. Chem. Rev. 1983, 83, 425.
6. Sheldon, R. A.; Kochi, J. K. “Metal Catalyzed Oxidation of Organic Compounds”; Academic Press: New York, 1981.
7. Eberson, L. Adv. Phys. Org. Chem. 1982, 18, 79.
8. Marcus, R. A. J. Chem. Phys. 1956, 24, 4966;
9. Adv. Phys. Org. Chem. 1965, 43, 679;
10. J. Phys. Chem. 1968, 72, 891.
11. Nicholson, R. S. Anal. Chem. 1965, 37, 1351.
12. Parker, V. D. J. Am. Chem. Soc. 1976, 98, 98.
13. Meites, L.; Zuman, P. “CRC Handbook Series in Organic Electrochemistry”; CRC Press: Cleveland, 1975, Vol. I, II.
14. Meites, L.; Zuman, P.; Rupp, E. B. J. Chem. Soc. Vol. III-V.
15. Nadjo, L.; Savéant, J.-M. J. Electroanal. Chem. 1973, 48, 113.
16. Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J. M.; Savéant, J.-M. J. Am. Chem. Soc. 1979, 101, 3431.
17. Eberson, L.; Jönsson, L.; Wistrand, L.-G. Acta Chem. Scand., Ser. B 1978, B32, 520.
18. Neikam, W. C.; Dimeler, G. R.; Desmond, M. M. J. Electrochem. Soc. 1964, 111, 1190.
19. Wightman, R. M. Anal. Chem. 1981, 53, 1125A.
20. Howell, J. O.; Wightman, R. M., unpublished results.
21. Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S. “Handbook of He(I) Photoelectron Spectra of Fundamental Organic Molecules”, Halstead Press: New York, 1981.
22. Klasinc, L.; Kovac, B.; Gusten, H. Pure Appl. Chem. 1983, 55, 289.
23. Peover, M. E. Electroanal. Chem. 1967, 2, 1.
24. Case, B. “Reactions of Molecules at Electrodes”; Hush, N. S., Ed.; Wiley: New York, 1971; p 25.
25. Larson, R. C.; Iwamoto, R. T.; Adams, R. N. Anal. Chim. Acta 1965, 25, 231.
26. Parker, V. D. J. Electroanal. Chem. 1969, 21, pp 1-3.
27. Fritz, H. P.; Artes, R. O. Electrochim. Acta 1981, 26, 417.
28. Kaiser, E. T., Kevan, L., Eds. “Radical Ions”; Wiley: New York, 1968.
29. Hammerich, O.; Moe, N. S.; Parker, V. D. J. Chem. Soc., Chem. Commun. 1972, 156.
30. Hammerich, O.; Parker, V. D. Electrochim. Acta 1973, 18, 537.
31. Eberson, L.; Jonsson, L.; Wistrand, L.-G. Acta Chem. Scand., Ser. B 1978, B32, 520.
32. Bewick, A.; Mellor, J. M.; Pons, B. S. Electrochim. Acta 1980, 25, 931.
33. Onopchenko, A.; Schulz, J. G. D.; Seekircher, R. J. Org. Chem. 1972, 37, 1414, p 123 f.
34. Iverson, D. J.; Hunter, G.; Blount, J. F.; Damewood, J. R., Jr.; Mislow, K. J. Am. Chem. Soc. 1981, 103, 6073.
35. Eberson, L.; Nyberg, K. Acc. Chem. Res. 1973, 6, 106.
36. Kochi, J. K.; Tang, R. T.; Bernath, T. J. Am. Chem. Soc. 1973, 95, 7114.
37. Rieke, R. D.; Tucker, I.; Milligan, S. N.; Wright, D. R.; Willeford, B. R.; Radonovich, L. J.; Eyring, M. W. Organometallics 1982, 1, 938.
38. Lloyd, M. K.; McCleverty, J. A.; Connor, J. A.; Jones, E. M. J. Chem. Soc., Dalton Trans. 1973, 1768.
39. Gubin, S. P.; Khandkarova, V. S. J. Organomet. Chem. 1970, 22, 449.
40. Milligan, S. N.; Tucker, I.; Rieke, R. D. Inorg. Chem. 1983, 22, 987.
41. Eberson, L. Acta. Chem. Scand., Ser. B 1978, B32, 237.
42. Nicholls, B.; Whiting, M. C. Proc. Chem. Soc. (London) 1958, 152;
43. J. Chem. Soc. 1959, 551.
44. Jackson, W. R.; Nicholls, B.; Whiting, M. C. J. Chem. Soc. 1960, 469.
45. Van Meurs, F.; Van der Toorn, J. M.; Van Bekkum, H. J. Organomet. Chem. 1976, 113, 341.
46. Razuvaev, G. A.; Kuzvetsov, V. A.; Egorochkin, A. N.; Klimov, A. A.; Artemov, A. N.; Sirotkin, N. I. J. Organomet. Chem. 1977, 128, 213.
47. Price, J. T.; Sorensen, T. S. Can. J. Chem. 1968, 46, 515.
48. Sneeden, R. P. E. “Organochromium Compounds”; Academic Press: New York, 1975; p 19ff.
49. Silverthorn, W. E. Adv. Organomet. Chem. 1975, 13, 48.
50. Atwood, J. D. J. Organomet. Chem. 1980, 196, 79.
51. Nakajima, T.; Toyota, A.; Kataoka, M. J. Am. Chem. Soc. 1982, 104, 5610.
52. Iwasaki, M.; Toriyama, K.; Nunome, K. J. Chem. Soc., Chem. Commun. 1983, 320.
53. Lofti, M.; Roberts, R. M. G. Tetrahedron 1979, 35, 2137.
54. Abraham, M. H. J. Am. Chem. Soc. 1982, 104, 2085.
55. Latimer, W. M.; Pitzer, K. S.; Slansky, C. M. J. Chem. Phys. 1939, 7, 108.
56. Noyes, R. M. J. Am. Chem. Soc. 1962, 84, 513.
57. Coetzee, J. F.; Campion, J. J. J. Chem. Soc. 1967, 89, 2513.
58. Tanaka, M. Inorg. Chem. 1976, 15, 2325.
59. Bockris, J. O. M.; Reddy, A. K. N. “Modern Electrochemistry”; Plenum: New York, 1970; Vol. 1, p 56ff.
60. Bewick, A.; Edwards, G. J.; Mellor, J. M.; Pons, B. S. J. Chem. Soc., Perkin Trans. 2 1977, 1952.
61. Nadjo, L.; Savéant, J.-M., cited in ref 9.
62. Dean, J. A., Ed. “Lange's Handbook of Chemistry”, 12th ed.; McGraw-Hill: New York, 1979.
63. Baumberger, R. S.; Parker, V. D. Acta Chem. Scand. 1980, B34, 537.
64. Nicholson, R. S.; Shain, I. Anal. Chem. 1964, 36, 706.
65. Amatote, C.; Savéant, J.-M. J. Electroanal. Chem. Interfacial Electrochem. 1977, 85, 27.
66. Miller, L. L.; Nordblom, G. D.; Mayeda, E. A. J. Org. Chem. 1972, 37, 916.
67. Pysh, E. S.; Yang, N. C. J. Am. Chem. Soc. 1963, 85, 2124.
68. Heilbronner, E.; Maier, J. P. “Electron Spectroscopy”; Brundle, C. R., Baker, A. D., Eds.; Academic Press: New York, 1977; Vol. 1, p 205ff.
69. Osa, T.; Yildiz, A.; Kuwana, T. J. Am. Chem. Soc. 1969, 91, 3994.
70. Mortensen, J.; Heinze, J. Angew. Chem., Int. Ed. Engl. 1984, 23, 84.
71. Guest, M. F.; Hillier, I. H.; Higginson, B. R.; Lloyd, D. R. Mol. Phys. 1975, 29, 113.
72. Muetterties, E. L.; Bleeke, J. R.; Wucherer, E. J.; Albright, T. A. Chem. Rev. 1982, 82, 499.
73. Albright, T. A.; Hofmann, P.; Hoffman, R. J. Am. Chem. Soc. 1977, 99, 7546.
74. Kobayashi, H.; Kobayashi, K.; Kaizu, Y. Inorg. Chem. 1981, 20, 4135
75. Gagne, R. R.; Koval, C. A.; Lisensky, G. C. Inorg. Chem. 1980, 19, 2854.
76. Kojima, H.; Bard, A. J. J. Am. Chem. Soc. 1975, 97, 6317.
77. Amatore, C.; Savéant, J.-M.; Tessier, D. J. Electroanal. Chem. Interfacial Electrochem. 1983, 146, 37; 1983, 147, 39.
78. Amatore, C.; Savéant, J.-M., unpublished results.
79. Klasinc, L.; Kovač, B.; Ruščić, B. Kent. Ind. 1974, 23, 56.