Revisiting the Effects of the Molecular Structure in the Kinetics of Electron transfer of Quinones: Kinetic Differences in Structural Isomers
DOI:
https://doi.org/10.29356/jmcs.v52i1.1041Keywords:
quinone, substituent effect, cyclic voltammety, innerreorganization energy, ESRAbstract
The effect of 2,5 and 2,6 disubstitution (R = CH3, Cl, C(CH3)3) for 1,4-benzoquinones, in the reorganization energy (l) for the first electron uptake process was analyzed in acetonitrile solution. Data obtained by cyclic voltammetry suggested differences in l for each type of disubstitution analyzed. These differences have important consequences in the stability and structure of the electrogenerated benzosemiquinone species, which was verified by performing in-situ spectroelectrochemical-ESR (Electron Spin Resonance) experiments of each disubstituted semiquinone.
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5. Aguilar-Martínez, M.; Bautista-Martínez, J.A.; Macías-Ruvalcaba, N. A.; González, I.; Tovar, E.; Marín del Alizal, T.; Collera, O.; Cuevas, G. J. Org. Chem. 2001, 66, 8349-8363
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7. Zuman, P. Collection Czech. Chem. Commun. 1960, 25, 3225-3244
8. Èársky, P.; Zuman, P. Collection Czech. Chem. Commun. 1969, 34, 497-503
9. Janzen, E. G. Acc. Chem. Res. 1969, 2, 279-288
10. Marcus, R. A. J. Chem. Phys. 1956, 24, 966-978
11. Marcus, R. A. Electrochim. Acta, 1968, 13, 995-1004
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14. Bard, A. J.; Faulkner, L. R. Electrochemical methods. Principles and applications. 2nd edition. John Wiley and Sons, United States of America. 2001
15. Rüssel, Ch.; Jaenicke, W. Z. Phys. Chem. N. F. 1984, 139, 97-112
16. Clegg, A. D.; Rees, N. V.; Klymenko, O. V.; Coles, B. A.; Compton, R. G. J. Phys. Chem. B. 2004, 108, 13047-13051
17. Nicholson, R. S. Anal. Chem. 1965, 37, 1351-1355
18. Rosanske, T. W.; Evans, D. H. J. Electroanal. Chem. 1976, 72, 277-285
19. Butler, J. A. V. Trans. Faraday. Soc., 1924, 19, 729-733 and 734-739
20. Erdey-Grúz, T.; Volmer, M. Z. Phys. Chem. 1930, 150A, 203-213
21. Weaver, M. J. Redox Reactions at Metal-Solution Interfaces (Chapter 1) in Comprehensive Chemical Kinetics, R. G. Compton (ed); Volume 27: Electrode Kinetics: Reactions, Elsevier Science and Technology, 1987
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23. Rüssel, Ch.; Jaenicke, W. J. Electroanal. Chem. 1986, 200, 249-260
24. Saveant, J. M.; Tessier, D. J. Phys. Chem. 1977, 81, 2192-2197
25. Andrieux, C. P.; Hapiot, P.; Savéant, J. M. J. Phys. Chem. 1988, 92, 5987-5992
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28. McConnell, J. Chem. Phys., 1956, 24, 764
29. Nelsen, S. F.; Blackstock, S. C.; Kim, Y. J. Am. Chem. Soc. 1987, 109, 677-682
30. Roe, D. K. “Overcoming Solution Resistance with Stability and Grace in Potentiostatic Circuits” in Laboratory Techniques in Electroanalytical Chemistry, Kissinger, P. T. and Heineman, W. R. (Editors). Marcel Dekker, Inc. New York, USA. 1996
31. He, P.; Faulkner, L. R. Anal. Chem. 1986, 58, 517-523
32. Gritzner, G.; Küta, J. Pure Appl. Chem., 1984, 4, 462
33. Stewart, J. P. P. J. Comput. Chem. 1989, 10, 209 and 221
34. Stewart, J. P. P. J. Comput. Chem. 1990, 11, 543
35. Stewart, J. P. P. J. Comput. Chem. 1990, 12, 320
36. Pietro, W. J.; Francl, M. M.; Hehre, W. J.; Defrees, D. J.; Pople, J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039-5048
37. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
38. Wertz, J. E.; Bolton, J. R. Electron Spin Resonance. First edition, Chapman and Hall, New York, 1972
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2019-07-29
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