Coupled electron-proton transfer in interactions of triplet C60 with hydrogen-bonded phenols: Effects of solvation, deuteration, and redox potentials

Journal of the American Chemical Society

Volumn 119, Issue 51, 1997, Pages 12601-12609

  Biczók, László ^a   Gupta, Neeraj ^a   Linschitz, Henry ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE; PYRIDINE;

ARTICLE; ELECTRON TRANSPORT; HYDROGEN BOND; OXIDATION REDUCTION REACTION; SOLVATION;

EID: 0031585677     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9727528     Document Type: Article

References (46)

1. Biczók, L.; Linschitz, H. J. Phys. Chem. 1995, 99, 1843.
2. Gupta, N.; Linschitz, H.; Biczók, L. Fullerene Sci. Technol. 1997, 5, 343.
3. Babcock, G. T.; Barry, B. A.; Debus, R. J.; Hoganson, C. W.; Atamian, M.; McIntosh, L.; Sithole, I.; Yocum, C. F. Biochemistry 1989, 28, 9557.
4. (a) Mataga, N.; Tsuno, S. Bull. Chem. Soc. Jpn. 1957, 30, 368.
5. (b) Miyasaka, H.; Tabata, A.; Ojima, S.; Ikeda, N.; Mataga, N. J. Phys. Chem. 1993, 97, 8222.
6. Dubois, D.; Moninot, G.; Kutner, W.; Jones, M. T.; Kadish, K. M. J. Phys. Chem. 1992, 96, 7137.
7. Andrews, L. J.; Deroulede, A.; Linschitz, H. J. Phys. Chem. 1978, 82, 2304.
8. (a) Biczok, L.; Linschitz, H.; Walter, R. I. Chem. Phys. Lett. 1992, 195, 339 and references therein. Ibid. 1994, 221, 188.
9. (a) Biczok, L.; Linschitz, H.; Walter, R. I. Chem. Phys. Lett. 1992, 195, 339 and references therein. Ibid. 1994, 221, 188.
10. (b) Andrews, L. J.; Levy, J. M.; Linschitz, H. J. Photochem. 1976, 6, 355.
11. (c) Steren, C. A.; van Willigen, H.; Biczok, L.; Gupta, N.; Linschitz, H. J. Phys. Chem. 1996, 100, 8920.
12. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, Germany, 1988.
13. Cauquis, G.; Deronzier, A.; Serre, S.; Vieil, E. Electroanal. Chem. Interfacial Electrochem. 1975, 60, 205.
14. Anne, A.; Habiot, P.; Moiroux, J.; Neta, P.; Saveant, J. M. J. Phys. Chem. 1991, 95, 2370.
15. Dierckx, A. M.; Huyskens, P.; Zeegers-Huyskens. J. Chim. Phys. 1965, 62, 336.
16. Gramstad, T. Acta Chem. Scand. 1961, 16, 807.
17. Joesten, M. H.; Schaad, L. J. Hydrogen Bonding; Marcel Dekker Inc.: New York, 1974.
18. Abraham, M. H.; Duce, P. P.; Prior, D. V.; Barrat, D. G.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 1355.
19. Titov, E. V.; Shurpach, V. I.; Belkina, G. A.; Gonchar, N. P. J. Mol. Struct. 1990, 219, 257.
20. Vasin, S. V. Russ. J. Phys. Chem. 1985, 59, 1138.
21. We give here only a brief summary of essential voltammetric results and interpretations regarding these phenol-additive systems, to relate to their quenching behavior, which is our main concern in this paper.
22. (a) Hammerich, O.; Parker, V. D.; Ronlan, A. Acta Chem. Scand. B 1976, 30, 89.
23. (b) Hammerich, O.; Parker, V. D. Acta Chem. Scand. B 1982, 36, 63 and references therein,
24. (c) Parker, V. D. In Encyclopedia of Electrochemistry of the Elements; Bard, A. J., Lund, H., Eds.; Dekker: New York, 1978; Vol. XI. pp 242-275.
25. Parker, V. D. Chem. Commun. 1969, 716.
26. Eggins, B. R. Chem. Commun. 1969, 1267.
27. Eggins, B. R.; Chambers, J. Q. J. Electrochem. Soc. 1970, 117, 186.
28. Richards, J. A.; Whitson, P. E.; Evans, D. H. J. Electroanal. Chem. 1975, 63, 311.
29. Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 6384, where H-bonding is shown to facilitate reversible quinone reduction.
30. Bordwell, F. G.; Cheng, J. P. J. Am. Chem. Soc. 1991, 113, 1736.
31. -1 for benzophenone ketyl: Inbar, S.; Linschitz, H.; Cohen, S. G. J. Am. Chem. Soc. 1981, 103, 7232).
32. -1 for benzophenone ketyl: Inbar, S.; Linschitz, H.; Cohen, S. G. J. Am. Chem. Soc. 1981, 103, 7232).
33. (b) Johnston, L. J.; Mathivanan, N.; Negri, F.; Siebrand, W.; Zerbetto, F. Can. J. Chem. 1993, 71, 1655.
34. Nasielski, J.; Nonckt, E. V. Spectrochem. Acta 1963, 19, 1989.
35. Kamat, P. V. J. Am. Chem. Soc. 1991, 113, 9705.
36. Reprinted from ref 2, p 346, by courtesy of Marcel Dekker, Inc.
37. Arbogast, J. W.; Foote, C. S.; Kao, M. J. Am. Chem. Soc. 1992, 114, 2277.
38. Arnett, E. M.; Mitchell, E. J. J. Am. Chem. Soc. 1971, 93, 4052.
39. Loeff, I.; Treinin, A.; Linschitz, H. J. Phys. Chem. 1983, 87, 2536.
40. Steadman, J.; Syage, J. A. J. Am. Chem. Soc. 1991, 113, 6786.
41. Peover M. E.; Davis, J. D. Trans. Faraday Soc. 1964, 60, 476.
42. (a) Maivanorskii, S. G. Catalytic and Kinetic Currents in Polarogarphy; Plenum: New York, 1968.
43. (b) Galus, G. Fundamentals of Electrochemical Analysis; Ellis Harwood: Chichester, U.K., 1976; Chapter 8.
44. We rule out phenoxide oxidation by this same kinetic process on the basis of the relatively small potential shift compared with that caused by TBAOH (see above).
45. Zeng, Y.; Biczók, L.; Linschitz, H. J. Phys. Chem. 1992, 96, 5237.
46. To conveniently distinguish three possible types of closely coupled electron-proton transfer, we suggest the term concerted for the case in which both particles move together from a common donor to the same acceptor, discerted, in which there is a common donor but different acceptors, and ascerted, for different donors to a common acceptor. The examples dealt with here represents discerted transfer. For situations in which motion of the electron and proton can clearly be shown to be sequential, we may replace ...certed by ...sequent. Electron transfer via a hydrogen-bond bridge, in which we have proton displacement but not transfer, represents yet another situation.