Dependence of intramolecular dissociative electron transfer rates on driving force in Donor-Spacer-Acceptor systems

Journal of the American Chemical Society

Volumn 120, Issue 23, 1998, Pages 5713-5722

  Antonello, Sabrina ^a   Maran, Flavio ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID; BROMIDE; BROMINE DERIVATIVE; CARBON;

ARTICLE; ELECTRON; ELECTRON TRANSPORT; FORCE; POTENTIOMETRY;

EID: 0032540704     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9741180     Document Type: Article

References (80)

1. For example, see: (a) Closs, G. L.; Miller, J. R. Science 1988, 240, 440. (b) Wasiliewski, M. R. Chem. Rev. 1992, 92, 435. (c) Paddon-Row, M. N. Acc. Chem. Res. 1994, 27, 18.
2. For example, see: (a) Closs, G. L.; Miller, J. R. Science 1988, 240, 440. (b) Wasiliewski, M. R. Chem. Rev. 1992, 92, 435. (c) Paddon-Row, M. N. Acc. Chem. Res. 1994, 27, 18.
3. For example, see: (a) Closs, G. L.; Miller, J. R. Science 1988, 240, 440. (b) Wasiliewski, M. R. Chem. Rev. 1992, 92, 435. (c) Paddon-Row, M. N. Acc. Chem. Res. 1994, 27, 18.
4. (a) Zhu, Y.; Schuster, G. B. J. Am. Chem. Soc. 1993, 115, 2190.
5. (b) Leon, W. J.; Whitten, D. G. J. Am. Chem. Soc. 1993, 115, 8038.
6. (c) Maslak, P. In Topics in Current Chemistry; Mattay, J., Ed.; Springer-Verlag: Berlin, 1993; Vol. 168, p 1.
7. (d) Wang, Y.; Lucia, L. A.; Schanze, K. S. J. Phys. Chem. 1995, 99, 1961.
8. (e) Gaillard, E. R.; Whitten, D. G. Acc. Chem. Res. 1996, 29, 292.
9. Eberson, L. Acta Chem. Scand. 1982, B36, 533.
10. (a) Savéant, J.-M. J. Am. Chem. Soc. 1987, 109, 6788.
11. (b) Savéant, J.-M. In Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI press: Greenwich, CT, 1994; Vol. 4, p 53.
12. (a) Savéant, J.-M. J. Phys. Chem. 1994, 98, 3716.
13. (b) Addock, W.; Andrieux, C. P.; Clark, C. I.; Neudeck, A.; Savéant, J.-M.; Tardy, C. J. Am. Chem. Soc. 1995, 117, 8285.
14. (c) Andrieux, C. P.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 1995, 117, 9340.
15. (d) Andrieux, C. P.; Savéant, J.-M.; Tallec, A.; Tardivel, R.; Tardy, C. J. Am. Chem. Soc. 1996, 118, 9788.
16. (e) Andrieux, C. P., Savéant, J.-M.; Tallec, A.; Tardivel, R.; Tardy, C. J. Am. Chem. Soc. 1997, 119, 2420.
17. (a) Andersen, M. L.; Mathivanan, N.; Wayner, D. D. M. J. Am. Chem. Soc. 1996, 118, 4871.
18. (b) Andersen, M. L.; Wayner, D. D. M. J. Electroanal. Chem. 1996, 412, 53.
19. (c) Andersen, M. L.; Long, W.; N.; Wayner, D. D. M. J. Am. Chem. Soc. 1997, 119, 6590.
20. Maslak, P.; Vallombroso, T. M.; Chapman, W. H., Jr.; Narvaez, J. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 73.
21. (a) Harsanyi, M. C.; Lay, P. A.; Norris, R. K.; Witting, P. K. J. Org. Chem. 1995, 60, 5487.
22. (b) Harsanyi, M. C.; Lay, P. A.; Norris, R. K.; Witting, P. K. Aust. J. Chem. 1996, 49, 581.
23. (c) Lay, P. A.; Norris, R. K.; Witting, P. K. Aust. J. Chem. 1996, 49, 1279.
24. Some interesting results concerning the distance effects in gas-phase dissociative electron attachments have been published: Pearl, D. M.; Burrow, P. D.; Nash, J. J.; Morrison, H.; Nachtigallova, D.; Jordan, K. D. J. Phys. Chem. 1995, 99, 12379.
25. (a) Workentin, M. S.; Maran, F.; Wayner, D. D. M. J. Am. Chem. Soc. 1995, 117, 2120.
26. (b) Donkers, R. L.; Maran, F.; Wayner, D. D. M.; Workentin, M. S. Work in progress.
27. Wayner, D. D. M.; Parker, V. D. Acc. Chem. Res. 1993, 26, 287.
28. Antonello, S.; Musumeci, M.; Wayner, D. D. M.; Maran, F. J. Am. Chem. Soc. 1997, 119, 9541.
29. (a) Lund, T.; Lund, H. Acta Chem. Scand. 1986, B40, 470.
30. (b) Pedersen, S. U.; Svensmark, B. Acta Chem. Scand. 1986, A40, 607.
31. (c) Andrieux, C. P.; Gallardo, L; Savéant, J.-M.; Su, K. B. J. Am. Chem. Soc. 1986, 108, 638.
32. Grimshaw, J.; Langan, J. R.; Salmon, G. A. J. Chem. Soc., Faraday Trans. 1994, 90, 75.
33. Savéant, J.-M. J. Am. Chem. Soc. 1992, 114, 10595.
34. Lund, H.; Daasbjerg, K.; Lund, T.; Pedersen, S. V. Acc. Chem. Res. 1995, 28, 313.
35. o)/4.
36. Antonello, S.; Maran, F. J. Am. Chem. Soc. 1997, 119, 12595.
37. Workentin, M. S.; Donkers, R. L. J. Am. Chem. Soc. 1998, 120, 2664. We are grateful to Prof. Workentin for providing us a copy of the manuscript prior to publication.
38. Kirk, D. N.; Shaw, P. M. J. Chem. Soc. C 1970, 182.
39. Courtot, P. Bull. Soc. Chim. Fr. 1962, 1493.
40. Bushweller, J. H.; Anzalone, L.; Spencer, T. A. Synth. Commun. 1989, 19, 745.
41. Brown, D.; Davies, B. T.; Halsall, T. G. J. Chem. Soc. 1963, 1095.
42. Jones, R. H.; Sondheimer, F. J. Chem. Soc. 1949, 615.
43. Antonello, S.; Gennaro, A.; Maran, F.; Venzo, A. To be published.
44. Farnia, G.; Maran, F.; Sandonà, G.; Severin, M. G. J. Chem. Soc., Perkin Trans. 2 1982, 1153.
45. Bard, A. J.; Faulkner, L. R. Electrochemical Methods, Fundamentals and Applications; Wiley: New York, 1980.
46. (a) Nicholson, R. S.; Shain, I. Anal. Chem. 1964, 36, 706.
47. (b) Nicholson, R. S. Anal. Chem. 1965, 37, 1351.
48. Nadjo, L.; Savéant, J.-M. J. Electroanal. Chem. 1973, 48, 113.
49. (a) Imbeaux, J. C.; Savéant, J.-M. J. Electroanal. Chem. 1973, 44, 169.
50. (b) Savéant, J.-M.; Tessier, D. J. Electroanal. Chem. 1975, 65, 57.
51. The two limiting values arise by either neglecting or by taking into account in the calculation a different solvation of the halide relative to the corresponding radical. For details, see refs 3 and 4b.
52. 12 In the hypothesis that the double-layer effects of glassy carbon and mercury are similar, we applied the same correction to the results obtained with 4 (the uncorrected E° is -1.13 V). We believe, however, that the error estimated for E°(±0.1 V) takes into account also possible double-layer differences.
53. 3,4b
54. p(4) > 0.2 V proved to be adequate.
55. 27a Since it is not completely clear how these decays take place (Wagenknecht, J. H.; Goodin, R. D.; Kinlen, P. J.; Woodard, F. E. J. Electrochem. Soc. 1984, 131, 1559), the above radical anions were discarded as candidate electron donors.
56. (a) Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J. M.; M'Halla, F.; Savéant J.-M. J. Electroanal. Chem. 1980, 113, 19.
57. (b) Andrieux, C. P.; Savéant J.-M. J. Electroanal. Chem. 1986, 205, 43.
58. ..
59. Daasbjerg, K.; Pedersen, S. U.; Lund, H. Acta Chem. Scand. 1991, 45, 424.
60. Maran, F.; Celadon, D.; Severin, M. G.; Vianello, E. J. Am. Chem. Soc. 1991, 113, 9320.
61. Andrieux, C. P.; Gallardo, I.; Savéant, J.-M. J. Am. Chem. Soc. 1989, 111. 1620.
62. Occhialini, D.; Pedersen, S. U.; Lund, H. Acta Chem. Scand. 1990, 44, 715.
63. (a) Maran, F.; Vianello, E.; D'Angeli, F.; Cavicchioni, G.; Vecchiati, G. J. Chem. Soc., Perkin Trans. 2 1987, 33.
64. (b) Maran, F.; Roffia, S.; Severin, M. G.; Vianello, E. Electrochim. Acta 1990, 35, 81.
65. (c) By acting as a proton donor, part of the starting material is transformed into a species that is not reducible at the working potentials. Accordingly, the number of exchanged electrons is less than expected. An increase of v tends to outrun the effect of self-protonation reactions. We are currently investigating the relevance of this reaction and of radical coupling reactions in the overall process.
66. Evans, D. H. J. Phys. Chem. 1972, 76, 1160.
67. p/∂log v varies form 29.6 mV/log v to 59.1 mV/log v (25 °C, α = 0.5) when the system passes from the former to the latter kinetic control. In the intermediate situation (ca. 6 orders of magnitude in v), a nonlinear peak potential shift connects the two limiting zones.
68. 4 both derivatives being calculated at the midpoint of the explored ΔG° range.
69. Marcus, R. A. J. Chem. Phys. 1956, 24, 966.
70. Closs, G. L.; Calcaterra, L. T.; Green, N. J.; Penfield, K. W.; Miller, J. R. J. Phys. Chem. 1986, 80, 3673.
71. Paulson, J. R.; Pramed, K.; Eaton, P.; Closs, G. L.; Miller, J. R. J. Phys. Chem. 1993, 97, 13042.
72. Kojima, H.; Bard, A. J. J. Am. Chem. Soc. 1975, 97, 6317.
73. (a) Sutin, N. Prog. Inorg. Chem. 1983, 30, 441.
74. (b) Sutin, N. In Electron Transfer in Inorganic, Organic, and Biological Systems: Bolton, J. R., Mataga, N., McLendon, G., Eds.; Advances in Chemistry Series 228; American Chemical Society: Washington, DC, 1991; p 25.
75. (a) Newton, M. D. Chem. Rev. 1991, 91, 767.
76. (b) Barbara, P. F.; Meyer, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148.
77. 10b.
78. (a) German, E. D.; Kuznetsov, A. M. J. Phys. Chem. 1994, 98, 6120.
79. (b) German, E. D.; Kuznetsov, A. M.; Tikhomirov, V. A. J. Phys. Chem. 1995, 99, 9095.
80. ET decreases more rapidly than expected. However, this is common to both the inter- and the intramolecular ETs and thus cannot be considered as a relevant factor in determining the difference between the observed a values.