Spectroscopic and electrochemical evaluation of salt effects on electron-transfer equilibria between donor/acceptor and ion-radical pairs in organic solvents

ChemPhysChem

Volumn 9, Issue 16, 2008, Pages 2406-2413

  Rosokha, Sergiy V ^a   Sun, Duoli ^a   Fisher, Jeffrey ^a   Kochi, Jay K ^a  

^a University of Houston   (United States)

Author keywords

Donor acceptor systems; Electron transfer; Ion pairs radical ions; Salt effect

Indexed keywords

CHARGE TRANSFER; DICHLOROMETHANE; ELECTROLYTES; ELECTRON TRANSITIONS; EQUILIBRIUM CONSTANTS; NEGATIVE IONS; REDOX REACTIONS;

APPARENT EQUILIBRIUM CONSTANT; DONOR-ACCEPTOR SYSTEM; ELECTROCHEMICAL EVALUATIONS; ELECTRON TRANSFER; RADICAL IONS; SALT EFFECT; TETRABUTYLAMMONIUM HEXAFLUOROPHOSPHATE; THREE ORDERS OF MAGNITUDE;

FREE RADICAL REACTIONS;

EID: 55549124540     PISSN: 14394235     EISSN: 14397641     Source Type: Journal    
DOI: 10.1002/cphc.200800470     Document Type: Article

References (58)

1. a) A. Loupy, B. Tchoubar, Salt effects in organic and organometallic chemistry, VCH, Weinheim, 1992;
2. b) A. Loupy, B. Tchoubar, D. Astruc, Chem. Rev. 1992, 92, 1141-1165.
3. Ions and ion pairs in organic reactions, Vols. 1 and 2 (Ed.: M. Szwarc), Wiley, New York, 1972.
4. a) E. M. Kosower, Introduction to physical organic chemistry, Wiley, New York, 1968;
5. b) E. T. Kaiser, L. Kevan, Radical ions, Interscience, New York, 1968;
6. c) A. Kumar, Chem. Rev. 2001, 101, 1-19;
7. d) A. Macchioni, Chem. Rev. 2005, 105, 2039-2073.
8. a) S. Winstein, E. Clippinger, A. H. Fainberg, J. C. Robinson, J. Am. Chem. Soc. 1954, 76, 2597-2598;
9. b) S. Winstein , J. C. Robinson, J. Am. Chem. Soc. 1958, 80, 169-181.
10. a) N. Hirota, R. Carraway, W. Schook, J. Am. Chem. Soc. 1968, 90, 3611-3618;
11. b) R. A. Marcus, J. Phys. Chem. B 1998, 102, 10071-10077.
12. a) J. Yuasa, T. Suenobu, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 12090-12091;
13. b) K. Okamoto, H. Imahori, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 7014-7021;
14. c) S. Fukuzumi, K. Ohkubo, T. Okamoto, J. Am. Chem. Soc. 2002, 124, 14147-14155;
15. d) K. Okamoto, K. Ohkubo, K. M. Kadish, S. Fukuzumi, J. Phys. Chem. A 2004, 108, 10405-10413;
16. e) S. Fukuzumi, H. Mori, T. Suenobu, Y. Araki, O. Ito, K. M. Kadish, J. Am. Chem. Soc. 2001, 123, 12458-12465.
17. a) J. D. Simon, K. S. Peters, J. Am. Chem. Soc. 1982, 104, 6142-6144;
18. b) P. A. Thompson, J. D. Simon, J. Am. Chem. Soc. 1993, 115, 5657-5664;
19. c) K. S. Peters, Acc. Chem. Res. 2007, 40, 1-7.
20. a) S. Sankararaman, W. A. Haney, J. K. Kochi, J. Am. Chem. Soc. 1987, 109, 7824-7838;
21. b) J. M. Masnovi, A. Levine, J. K. Kochi, J. Am. Chem. Soc. 1985, 107, 4356-4358;
22. c) T. M. Bockman, J. K. Kochi, J. Chem. Soc. Perkin Trans. 2 1994, 1901-1915;
23. d) V. N. Grosso, C. M. Previtali, C. A. Chesta, Photochem. Photobiol. 1998, 68, 481-486;
24. e) M. Mac, J. Wirz, Photochem. Photobiol. Sci. 2002, 1, 24-29.
25. a) J. K Kochi, Adv. Phys. Org. Chem. 1994, 29, 185-272;
26. b) R. Rathore, J. K. Kochi, Adv. Phys. Org. Chem. 2000, 35, 193-318.
27. For the salt effects on related redox equilibria, see: a) J. Ruiz, M. Lacoste, D. Astruc, J. Chem. Soc. Chem. Commun. 1989, 813-814;
28. b) M. H. Delville, M. Lacoste, D. Astruc, J. Am. Chem. Soc. 1992, 114, 8310-8311;
29. c) T. M. Bockman, J. K. Kochi, New J. Chem. 1992, 16, 39-49.
30. [12]
31. a) J. E. Gordon, Organic chemistry of electrolyte solutions, Wiley, New York, 1975;
32. b) H. S. Harned, B. B. Owen, Physical chemistry of electrolytic solutions, Chapman-Reinhold, New York, 1958.
33. a) J. Yuasa, T. Suenobu, S. Fukuzumi, ChemPhysChem 2006, 7, 942-954;
34. b) S. V. Rosokha, J. M. Lu, M. D. Newton, J. K. Kochi, J. Am. Chem. Soc. 2005, 127, 7411-7420;
35. c) J. Yuasa, S. Yamada, S. Fukuzumi, Chem. Eur. J. 2008, 14, 1866-1874.
36. a) F. Barriere, W. E. Geiger, J. Am. Chem. Soc. 2006, 128, 3980-3989;
37. b) A. Nafady, T. T. Chin, W. E. Geiger, Organometallics 2006, 25, 1654-1663.
38. a) D.-L. Sun, S. V. Rosokha, J. K. Kochi, J. Phys. Chem. B 2007, 111, 6655-6666;
39. -.} represent herein (either in contact or separated) ion pairs or solvated "free" ion radicals.
40. S. V. Rosokha, J. K. Kochi, J. Am. Chem. Soc. 2007, 129, 3683-3697.
41. a) M. Meloun, J. Havel, E. Hogfeldt, Computation of solution equilibria, Wiley, New-York, 1988;
42. b) A. E. Martel, R. J. Motecaitis, The determination and use of stability constants, VCH, Weinheim, 1988;
43. [17a,b]
44. a) A. J. Bard, L. R. Faulkner, Electrochemical methods. Fundamentals and applications, Wiley, New York, 1980;
45. b) P. H. Rieger, Electrochemistry, Chapman & Hall, New York, 1994;
46. o, which are based on the activities of the redox species (see discussion in refs. [17a] and [17b]).
47. 6, see Figure 3).
48. ET values.
49. a) Y. Marcus, G. Hefter, Chem. Rev. 2006, 106, 4585-4621;
50. [20a]
51. P. Atkins, Physical Chemistry, Freeman, New York, 1998.
52. G. G. Manov, R. G. Bates, W. J. Hamer, S. F. Acree, J. Am. Chem. Soc. 1943, 65, 1765-1767.
53. 6 concentrations between about 0.02 and about 0.2M, especially for the TMPD/TCNE pair. This result indicates that under such conditions, the electron-transfer equilibria might be noticeably affected by interactions between oppositely charged ion radicals (and/or neutral donors and acceptors).
54. T. J. Reddy, T. Iwama, H. J. Halpern, V. H. Rawal, J. Org. Chem. 2002, 67, 4635-4639.
55. a) I. Noviandri, K. N. Brown, D. S. Fleminf, P. T. Gulyas, P. A. Lay, A. F. Masters, L. Phillips, J. Phys. Chem. B 1999, 103, 6713-6722;
56. b) J. R. Aranzaes, M.-C. Daniel, D. Astruc, Can. J. Chem. 2006, 84, 288-299.
57. S. Katsuta, H. Wakabayashi, M. Tamaru, Y. Kudo, Y. Takeda, J. Solution Chem. 2007, 36, 531-547.
58. W. Rocchia, S. Sridharan, A. Nicholls, E. Alexov, A. Chiabrera, B. Honig, J. Comput. Chem. 2002, 23, 128-137.