Change in reaction pathway in the reduction of 3,5-Di-tert-butyl-1,2- benzoquinone with increasing concentrations of 2,2,2-trifluoroethanol

Journal of Physical Chemistry B

Volumn 110, Issue 43, 2006, Pages 22043-22047

  Macías Ruvalcaba, Norma A ^a   Okumura, Noriko ^a   Evans, Dennis H ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; ELECTROCHEMISTRY; FREE RADICALS; REACTION KINETICS;

CONCERTED PROTON AND ELECTRON- TRANSFER REACTION (CPET); PROTON TRANSFER;

AROMATIC COMPOUNDS;

EID: 33751290622     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp064003v     Document Type: Article

References (34)

1. Chambers, J. Q. In The Chemistry of the Quinonoid Compounds; Fatai, S., Rappaport, Z., Eds.; Wiley: New York, 1988; Vol. 2, Part 1, pp 719-757.
2. Aguilar-Martínez, M.; Macías-Ruvalcaba, N. A.; Bautista-Martínez, J. A.; Gómez, M.; Gonzalez, F. J.; Gonzalez, I. Curr. Org. Chem. 2004, 8, 1721-1738.
3. (a) Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 6384-6391.
4. (b) Ge, Y.; Lilienthal, R. R.; Smith, D. K. J. Am. Chem. Soc. 1996, 118, 3976-3977.
5. (c) Goulart, M. O. F.; de Abreu, F. C.; Ferraz, P. A. L.; Tonholo, J.; Glezer, V. In Novel Trends in Electroorganic Synthesis; Torii, S., Ed.; Springer-Verlag: Tokyo, 1998; pp 359-362.
6. (d) Okumura, N.; Uno, B. Bull. Chem. Soc. Jpn. 1999, 72, 1213-1217.
7. (e) Aguilar-Martínez, M.; Cuevas, G.; Jiménez-Estrada, M.; Gonzalez, I.; Lotina-Hennsen, B.; Macífas-Ruvalcaba, N. J. Org. Chem. 1999, 64, 3684-3694.
8. (f) Uno, B.; Okumura, N.; Goto, M.; Kano, K. J. Org. Chem. 2000, 65, 1448-1455.
9. (g) Ge, Y.; Smith, D. K. Anal. Chem. 2000, 72, 1860-1865.
10. (h) Ge, Y.; Miller, L.; Ouimet, T.; Smith, D. K. J. Org. Chem. 2000, 65, 8831-8838.
11. (i) Ferraz, P. A. L.; de Abreu, F. C.; Pinto, A. V.; Glezer, V.; Tonholo, J.; Goulart, M. O. F. J. Electroanal. Chem. 2001, 507, 275-286.
12. (j) Aguilar-Martínez, M.; Bautista-Martínez, J. A.; Macías-Ruvalcaba, N.; Gonzalez, L; Tovar, E.; del Alizal, T. M.; Collera, O.; Cuevas, G. J. Org. Chem. 2001, 66, 8349-8363.
13. (k) Gómez, M.; González, F. J.; Gonzalez, I. J. Electro ehem. Soc. 2003, 750, E527-E534.
14. Garza, J.; Vargas, R.; Gómez, M.; González, L; González, F. J. J. Phys. Chem. A 2003, 107, 11161-11168.
15. Gómez, M.; González, I.; González, F. J.; Vargas, R.; Garza, J. Electrochem. Commun. 2003, 5, 12-15.
16. (n) Gómez, M.; Gómez-Castro, C. Z.; Padilla-Martfnez, I. I.; Martínez-Martínez, F. J.; González, F. J. J. Electroanal. Chem. 2004, 567, 269-276.
17. (o) Macías-Ruvalcaba, N. A.; González, I.; Aguilar-Martínez, M. J. Electrochem. Soc. 2004, 151, E110-E118.
18. (p) Okumura, N.; Evans, D. H. In Analytical, Mechanistic and Synthetic Organic Electrochemistry. Sixth International Manuel M. Baizer Symposium in Honor of Dennis H. Evans and Masao Tokuda; Lessard, J., Hapiot, P., Taniguchi, I., Eds.; Electrochemical Society: Pennington, NJ; PV 2004-10, pp 21-24.
19. (q) Gómez, M.; González, F. J.; González, I. J. Electroanal. Chem. 2005, 575, 193-202.
20. Lehmann, M. W.; Evans, D. H. J. Phys. Chem. B 2001, 105, 8877-8884.
21. (a) Costentin, C.; Evans, D. H.; Robert, M.; Savéant, J.-M.; Singh, P. S. J. Am. Chem. Soc. 2005, 727, 12490-12491.
22. (b) Singh; P. S.; Evans, D. H. J. Phys. Chem. B 2006, 110, 637-644.
23. Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2006, 125, 4552-4553.
24. Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2006, 125, 8726-8727.
25. Macías-Ruvalcaba, N. A.; Evans, D. H. J. Phys. Chem. B 2005, 109, 14642-14647.
26. (a) Rudolph, M. J. Electroanal. Chem. 2003, 543, 23-29.
27. (b) Rudolph, M. J. Electroanal. Chem. 2004, 577, 289-307.
28. (c) Rudolph, M. J. Electroanal. Chem. 2003, 555, 171-176.
29. (d) Rudolph, M. J. Comput. Chem. 2005, 26, 619-632.
30. (e) Rudolph, M. J. Comput. Chem. 2005, 26, 633-641.
31. (f) Rudolph, M. J. Comput. Chem. 2005, 26, 1193-1204.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; C. Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
33. HA ≥ 50 mM. Thus, the fraction of anion radical present as the 3:1 complex will increase in proportion to CHA- (b) Harris, D. C. Quantitative Chemical Analysis, 6th ed.; Freeman: New York, 2003; pp 269-272.
34. Izutsu, K. Electrochemistry in Nonaqueous Solutions; Wiley-VCH: Weinheim, 2002; pp 70-75.