Oxidation of 4-methylanisole by aqueous cerium(IV) in a two-phase immiscible liquid/liquid system: Interfacial versus homogeneous control

Journal of Physical Chemistry B

Volumn 106, Issue 11, 2002, Pages 3019-3025

  Slevin, Christopher J ^a   Zhang, Jie ^a   Unwin, Patrick R ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ULTRAMICROELECTRODE VOLTAMMETRY;

CERIUM; ELECTRON TRANSITIONS; OXIDATION; POSITIVE IONS; RATE CONSTANTS; SOLUBILITY; SOLUTIONS; SURFACE CHEMISTRY; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

AROMATIC COMPOUNDS;

EID: 0037149805     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp013818v     Document Type: Article

References (55)

1. Atherton, J.H. Res. Chem. Kinet. 1994, 2, 193.
2. Freiser, H. Chem. Rev. 1980, 88, 611.
3. Danesi, P.R.; Chiarizia, R. CRC Crit. Rev. Anal. Chem. 1980, 10, 1.
4. Tzedakis, T.; Savall, A. Chem. Eng. Sci. 1991, 46, 2269.
5. Tzedakis, T.; Savall, A.J. Ind. Eng. Chem. Res. 1992, 31, 2475.
6. Tzedakis, T.; Savall, A.J. J. Appl. Electrochem. 1997, 27, 589.
7. Eberson, L. J. Am. Chem. Soc. 1983, 105, 3192.
8. Baciocchi, E.; Bietti, M.; Mattioli, M. J. Org. Chem. 1993, 58, 7106.
9. Ito, O.; Akiho, S.; Iino, M. J. Org. Chem. 1989, 54, 2436.
10. Schlesener, C.J.; Kochi, J.K. J. Org. Chem. 1984, 49, 3142.
11. Reed, R.A.; Murray, R.W. J. Electroanal. Chem. 1990, 285, 149.
12. Baciocchi, E.; Rol, C.; Mandolini, L. J. Am. Chem. Soc. 1980, 102, 7597.
13. Kreh, R.P.; Spotnitz, R.M.; Lundquist, J.T. Tetrahedron Lett. 1987, 28, 1068.
14. Ho, T.-L. Synthesis 1973, 347.
15. Trahanovsky, W.S.; Young, L.B. J. Org. Chem. 1966, 31, 3.
16. Torii, S.; Tanaka, H.; Inokuchi, T.; Nakane, S.; Akada, M.; Saito, N.; Sirakawa, T. J. Org. Chem. 1982, 47, 1647.
17. Pletcher, D.; Valdes, E.M. J. Chem. Res. (S) 1987, 386.
18. (a) Girault, H.H.; Schiffrin, D.J. In Electroanalytical Chemistry; Bard, A.J., Ed.; Marcel Dekker: New York, 1989; Vol. 15, p 1.
19. (b)Vanýsek, P. Electrochim. Acta 1995, 40, 2841.
20. (c) Volkov, A.G.; Deamer, D.W., Eds. Liquid-Liquid Interfaces: Theory and Methods; CRC Press: Boca Raton, FL, 1996.
21. For recent examples of ET reactions at liquid/liquid interfaces, see, for example: (a) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Phys. Chem. B 1996, 100, 17 881. (b) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Am. Chem. Soc. 1997, 119, 10 785. (c) Fermin, D.J.; Ding, Z.; Duong, D.H.; Brevet, P.F.; Girault, H.H. J. Phys. Chem. B 1998, 102, 10 334. (d) Fermin, D.J.; Duong, H.D.; Ding, Z.; Brevet, P.F.; Girault, H.H. J. Am. Chem. Soc. 1999, 121, 10 203. (e) Barker, A.L.; Unwin, P.R.; Amemiya, S.; Zhou, J.; Bard, A.J. J. Phys. Chem. B 1999, 103, 7260. (f) Cunnane, V.J.; Geblewicz, G.; Schiffrin, D. J. Electrochim. Acta 1995, 40, 3005. (g) Cheng, Y.F.; Schiffrin, D.J. J. Chem. Soc., Faraday Trans. 1993, 89, 199.
22. For recent examples of ET reactions at liquid/liquid interfaces, see, for example: (a) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Phys. Chem. B 1996, 100, 17 881. (b) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Am. Chem. Soc. 1997, 119, 10 785. (c) Fermin, D.J.; Ding, Z.; Duong, D.H.; Brevet, P.F.; Girault, H.H. J. Phys. Chem. B 1998, 102, 10 334. (d) Fermin, D.J.; Duong, H.D.; Ding, Z.; Brevet, P.F.; Girault, H.H. J. Am. Chem. Soc. 1999, 121, 10 203. (e) Barker, A.L.; Unwin, P.R.; Amemiya, S.; Zhou, J.; Bard, A.J. J. Phys. Chem. B 1999, 103, 7260. (f) Cunnane, V.J.; Geblewicz, G.; Schiffrin, D. J. Electrochim. Acta 1995, 40, 3005. (g) Cheng, Y.F.; Schiffrin, D.J. J. Chem. Soc., Faraday Trans. 1993, 89, 199.
23. For recent examples of ET reactions at liquid/liquid interfaces, see, for example: (a) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Phys. Chem. B 1996, 100, 17 881. (b) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Am. Chem. Soc. 1997, 119, 10 785. (c) Fermin, D.J.; Ding, Z.; Duong, D.H.; Brevet, P.F.; Girault, H.H. J. Phys. Chem. B 1998, 102, 10 334. (d) Fermin, D.J.; Duong, H.D.; Ding, Z.; Brevet, P.F.; Girault, H.H. J. Am. Chem. Soc. 1999, 121, 10 203. (e) Barker, A.L.; Unwin, P.R.; Amemiya, S.; Zhou, J.; Bard, A.J. J. Phys. Chem. B 1999, 103, 7260. (f) Cunnane, V.J.; Geblewicz, G.; Schiffrin, D. J. Electrochim. Acta 1995, 40, 3005. (g) Cheng, Y.F.; Schiffrin, D.J. J. Chem. Soc., Faraday Trans. 1993, 89, 199.
24. For recent examples of ET reactions at liquid/liquid interfaces, see, for example: (a) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Phys. Chem. B 1996, 100, 17 881. (b) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Am. Chem. Soc. 1997, 119, 10 785. (c) Fermin, D.J.; Ding, Z.; Duong, D.H.; Brevet, P.F.; Girault, H.H. J. Phys. Chem. B 1998, 102, 10 334. (d) Fermin, D.J.; Duong, H.D.; Ding, Z.; Brevet, P.F.; Girault, H.H. J. Am. Chem. Soc. 1999, 121, 10 203. (e) Barker, A.L.; Unwin, P.R.; Amemiya, S.; Zhou, J.; Bard, A.J. J. Phys. Chem. B 1999, 103, 7260. (f) Cunnane, V.J.; Geblewicz, G.; Schiffrin, D. J. Electrochim. Acta 1995, 40, 3005. (g) Cheng, Y.F.; Schiffrin, D.J. J. Chem. Soc., Faraday Trans. 1993, 89, 199.
25. For recent examples of ET reactions at liquid/liquid interfaces, see, for example: (a) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Phys. Chem. B 1996, 100, 17 881. (b) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Am. Chem. Soc. 1997, 119, 10 785. (c) Fermin, D.J.; Ding, Z.; Duong, D.H.; Brevet, P.F.; Girault, H.H. J. Phys. Chem. B 1998, 102, 10 334. (d) Fermin, D.J.; Duong, H.D.; Ding, Z.; Brevet, P.F.; Girault, H.H. J. Am. Chem. Soc. 1999, 121, 10 203. (e) Barker, A.L.; Unwin, P.R.; Amemiya, S.; Zhou, J.; Bard, A.J. J. Phys. Chem. B 1999, 103, 7260. (f) Cunnane, V.J.; Geblewicz, G.; Schiffrin, D. J. Electrochim. Acta 1995, 40, 3005. (g) Cheng, Y.F.; Schiffrin, D.J. J. Chem. Soc., Faraday Trans. 1993, 89, 199.
26. For recent examples of ET reactions at liquid/liquid interfaces, see, for example: (a) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Phys. Chem. B 1996, 100, 17 881. (b) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Am. Chem. Soc. 1997, 119, 10 785. (c) Fermin, D.J.; Ding, Z.; Duong, D.H.; Brevet, P.F.; Girault, H.H. J. Phys. Chem. B 1998, 102, 10 334. (d) Fermin, D.J.; Duong, H.D.; Ding, Z.; Brevet, P.F.; Girault, H.H. J. Am. Chem. Soc. 1999, 121, 10 203. (e) Barker, A.L.; Unwin, P.R.; Amemiya, S.; Zhou, J.; Bard, A.J. J. Phys. Chem. B 1999, 103, 7260. (f) Cunnane, V.J.; Geblewicz, G.; Schiffrin, D. J. Electrochim. Acta 1995, 40, 3005. (g) Cheng, Y.F.; Schiffrin, D.J. J. Chem. Soc., Faraday Trans. 1993, 89, 199.
27. For recent examples of ET reactions at liquid/liquid interfaces, see, for example: (a) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Phys. Chem. B 1996, 100, 17 881. (b) Tsionsky, M.; Bard, A.J.; Mirkin, M.V. J. Am. Chem. Soc. 1997, 119, 10 785. (c) Fermin, D.J.; Ding, Z.; Duong, D.H.; Brevet, P.F.; Girault, H.H. J. Phys. Chem. B 1998, 102, 10 334. (d) Fermin, D.J.; Duong, H.D.; Ding, Z.; Brevet, P.F.; Girault, H.H. J. Am. Chem. Soc. 1999, 121, 10 203. (e) Barker, A.L.; Unwin, P.R.; Amemiya, S.; Zhou, J.; Bard, A.J. J. Phys. Chem. B 1999, 103, 7260. (f) Cunnane, V.J.; Geblewicz, G.; Schiffrin, D. J. Electrochim. Acta 1995, 40, 3005. (g) Cheng, Y.F.; Schiffrin, D.J. J. Chem. Soc., Faraday Trans. 1993, 89, 199.
28. (a) Slevin, C.J.; Unwin, P.R. Langmuir 1997, 13, 4799.
29. (b) Slevin, C. J.; Unwin, P.R. Langmuir 1999, 15, 7361.
30. (c) Zhang, J.; Slevin, C.J.; Unwin, P.R. Chem. Commun. 1999, 1501.
31. (d) Zhang, J.; Unwin, P.R. J. Phys. Chem. B 2000, 104, 2341.
32. (e) Zhang, J.; Unwin, P.R. Phys. Chem. Chem. Phys. 2000, 2, 1267.
33. (f) Zhang, J.; Barker, A.L.; Unwin, P.R. J. Electroanal. Chem. 2000, 483, 95.
34. (g) Zhang, J.; Slevin, C.J.; Murtomäki, L.; Kontturi, K.; Williams, D.E.; Unwin, P.R. Langmuir 2001, 17, 821.
35. Slevin, C.J.; Unwin, P.R.; Zhang, J. In Liquid/interfaces in Chemical, Biological and Pharmaceutical Applications; Volkov, A.G., Ed.; Marcel Dekker: New York, 2000; pp 325-354.
36. Hanna, G.J.; Noble, R.D. Chem. Rev. 1985, 85, 583.
37. Marcus, R.A. J. Phys. Chem. 1990, 94, 1050.
38. Schmickler, W. J. Electroanal. Chem. 1997, 428, 123.
39. Wightman, R.M.; Wipf, D.O. In Electroanalytical Chemistry; Bard, A.J., Ed.; Marcel Dekker: New York, 1989; Vol. 15, p 267.
40. Saito, Y. Rev. Polarogr. Jpn. 1968, 15, 177.
41. Randle, T.H.; Kuhn, A.T. J. Chem. Soc., Faraday Trans. 1 1983, 79, 1741.
42. Bard, A.J.; Faulkner, L.R. Electrochemical Methods, Fundamentals and Applications; John Wiley and Sons: New York, 1980.
43. (a) Hawley, M.D.; Feldberg, S.W. J. Phys. Chem. 1966, 70, 3459.
44. (b) Andrieux, C.P.; Savéant, J.-M. J. Electroanal. Chem. 1989, 267, 15.
45. (c) Amatore, C.; Gareil, M.; Savéant, J.-M. J. Electroanal. Chem. 1983, 147, 1.
46. Hlavatý, J. J. Appl. Electrochem. 1994, 24, 989.
47. Parker, V.D.; Adams, R.N. Tetrahedron Lett. 1969, 21, 1721.
48. Marquez, J.; de Marquez, O.P. Rev. Roum. Chem. 1993, 38, 775.
49. Fleischmann, M.; Lasserre, F.; Robinson, J. J. Electroanal. Chem. 1984, 177, 115.
50. Slevin, C.J. Ph.D. Thesis, University of Warwick, 1999.
51. Richens, D.T. The Chemistry of Aqua Ions; Wiley: Chichester, 1997.
52. The Merck Index, Merck, Whitehouse Station, NJ, 1996.
53. Strutwolf, J.; Barker, A.L.; Gonsalves, M.; Caruana, D.J.; Unwin, P.R.; Williams, D.J.; Webster, J.R.P. J. Electroanal. Chem. 2000, 883, 163.
54. Benjamin, I. Chem. Rev. 1996, 96, 1449.
55. Marcus, R.A. J. Phys. Chem. 1991, 95, 2010.