The electron transfer (ET) reaction between benzylthioacetic acid (BTAA) and tris(1,10-phenanthroline)iron(III) perchlorate resulted in the formation of benzylsulfinylacetic acid. The reaction is first order with respect to both BTAA and [Fe(phen)3]3+ and is retarded by hydrogen ion. The ET reaction is studied in 50 % aqueous methanol medium. The Marcus theory is successfully applied to the present redox system and this supports the operation of single electron transfer in the rate controlling step of the reaction.
1. Sheddon, RA, Kochi, JK 1981 Metal catalysed oxidations of organic compounds Academic Press New York.
2. PR Oritz de Montellano eds. 1995 Cytochrome P-450, structure, mechanism and biochemistry Plenum Press New York.
3. Jorgensen, KA, Schiott, B 1990 Chem Rev 90:1483 .
4. Drago, RS 1992 Coord Chem Rev 117:185 .
5. Canali, L, Sherrington, DC 1999 Chem Soc Rev 28:85 .
6. Samsel, EG, Srinivasan, K, Kochi, JK 1985 J Am Chem Soc 107:7606 .
7. Leung, WH, Che, CM 1989 Inorg Chem 28:4619 .
8. Bousquet, C, Gilheany, DG 1995 Tetrahedron Lett 36:7739 .
9. Jacobsen EN (1995) In: Abel EW, Stone FGA, Wilkinson G, Hegedus LS (eds) Comprehensive organometallic chemistry-II, vol 12. Pergamon, New York, p 1097.
10. Finney, NS, Pospisil, PJ, Chang, S, Palucki, M, Konsler, RG, Hansen, KB, Jacobsen, EN 1997 Angew Chem Int Ed Engl 36:1720 .
11. Linde, C, Arnold, M, Norrby, P, Akermark, B 1997 Angew Chem Int Ed Engl 36:1723 .
12. Jacobsen EN (1993) In: Ojima I (ed) Catalytic asymmetric synthesis. VCH Weinheim, New York.
13. Chellamani, A, Alhaji, NMI, Rajagopal, S 1997 J Chem Soc Perkin Trans 2:299.
14. Chellamani, A, Kulandaipandi, P, Rajagopal, S 1999 J Org Chem 64:2232 .
15. Baciocchi, E, Lanzalunga, O, Marconi, F 1994 Tetrahedron Lett 35:9771 .
16. Fakuzumi, S, Nakanishi, I, Tanak, K, Suenobu, T, Tabard, A, Guilard, R, Caemelbecke, EV, Kadish, KM 1999 J Am Chem Soc 121:785 .
17. Meunier, B, Sorokin, A 1997 Acc Chem Res 30:470 .
18. Marcus, RA 1965 J Chem Phys 43:679 .
19. Sutin, N 1983 Inorg Chem 30:441.
20. Guarr, T, Mclendon, G 1985 Coord Chem Rev 68:1 .
21. Barbara, PF, Meyer, TJ, Ratner, MA 1996 J Phys Chem 100:13148 .
22. Balzani, V 2001 Electron transfer in chemistry Wiley-VCH Weinheim .
23. Wong, CL, Kochi, JK 1979 J Am Chem Soc 101:5593 .
24. Ford-Smith, MH, Sutin, N 1961 J Am Chem Soc 83:1830 .
25. Beller, G, Lente, G, Fabian, I 2010 Inorg Chem 49:3968 .
26. Eyring, H 1935 J Chem Phys 3:107 .
27. Lente, G, Fabian, I, Poe, AJ 2005 New J Chem 29:759 .
28. Eberson, L 1987 Electron transfer reactions in organic chemistry Springer Heidelberg .
29. Kochi, JK 1990 Acta Chem Scan 44:409 .
30. Holland, HL 1988 Chem Rev 88:473 .
31. Damani LA (eds) (1989) Sulphur containing drugs and related organic compounds—chemistry, biochemistry and toxicology. I(B): metabolism of sulphur functional groups. Chichester.
32. Sustin, N, Gordon, BM 1961 J Am Chem Soc 83:70 .
33. George P , Irvine DH (1954) J Chem Soc 587.
34. Baxendale, JH, Bridge, NK 1955 J Phys Chem 59:785 .
35. Srinivasan, C, Chellamani, A, Kuthalingam, P 1982 J Org Chem 47:428 .
36. Bobrowski, GK, Hug, GL, Pogocki, D, Marciniak, B, Schoneich, C 2007 J Am Chem Soc 129:9236 .
37. Uneyama, K, Torii, S 1971 Tetrahedron Lett 21:329 .
38. Ohe, T, Mashino, T, Hirobe, M 1995 Tetrahedron Lett 42:7681 .
39. Weber, L, Hommel, R, Behling, J, Hanfe, G, Hannig, H 1994 J Am Chem Soc 116:2400 .
40. Srinivasan, C, Chellamani, A, Rajagopal, S 1985 J Org Chem 50:1201 .
41. Srinivasan, C, Rajagopal, S, Chellamani, A 1990 J Chem Soc Perkin Trans 2:1839.
42. Baciocchi, E, Intini, D, Piermattei, A, Rol, C, Ruzziconi, R 1989 Gazz Chim Ital 119:649.
43. Acquaye, JH, Muller, JG, Takeuchi, K 1993 J Inorg Chem 32:160 .
44. Watanabe, Y, Iyanagi, T, Oae, S 1980 Tetrahedron Lett 21:3685 .
45. Padgette, SR, Wimalasena, K, Herman, HH, Sirimanne, SR, May, SW 1985 Biochemistry 24:5826 .
46. Allen Gnanaraj, G, Rajagopal, S, Srinivasan, C 1992 Ind Acad Sci 104:9.
47. Allen Gnanaraj, G, Rajagopal, S, Srinivasan, C, Pitchumani, K 1993 Tetrahedron 49:4721 .
48. Allen Gnanaraj, G, Rajagopal, S, Srinivasan, C 1994 J Tetrahedron 50:9447 .
49. Ruff, I, Zimonyi, M 1973 Electrochem Acta 18:515 .
50. Aderinsewo, CO, Adegite, A 1979 Inorg Chem 12:3597 .
51. Gratzel, M 1989 Heterogeneous photochemical electron transfer CRC Press Boca Raton.
52. Sarala, R, Stanbury, DM 1990 Inorg Chem 29:3456 .
53. Sarala, R, Stanbury, DM 1992 Inorg Chem 3:2771 .
54. Sarala, R, Rubin, SB, Stanbury, DM 1991 Inorg Chem 30:3999 .
55. Brinck, T, Carlqvist, P, Holm, AH, Dassbjerg, K 2002 J Phys Chem A 106:8827 .
56. Larsen, AG, Holm, AH, Roberson, M, Daasbjerg, K 2001 J Am Chem Soc 123:1723 .