AM1-SM2 calculations model the redox potential of nitroxyl radicals such as TEMPO

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6745-6749

  Rychnovsky, Scott D ^a   Vaidyanathan, Rajappa ^a   Beauchamp, Thomas ^a   Lin, Rong ^a   Farmer, Patrick J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITROXYL RADICAL; OXO AMMONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; CYCLIC POTENTIOMETRY; MATHEMATICAL COMPUTING; OXIDATION; OXIDATION REDUCTION REACTION; PREDICTION;

EID: 0032888074     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990636c     Document Type: Article

References (37)

1. (a) Naik, N.; Braslau, R. Tetrahedron 1998, 54, 667-96.
2. (b) de Nooy, A. E. J.; Besemer, A. C.; Bekkum, H. v. Synthesis 1996, 1153-74.
3. (c) Bobbitt, J. M.; Flores, M. C. L. Heterocycles 1988, 27, 509-33.
4. (a) Ma, Z.; Huang, Q.; Bobbitt, J. M. J. Org. Chem. 1993, 58, 4837-43.
5. (b) Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535-7.
6. (c) Yanagisawa, Y.; Kashiwagi, Y.; Kurashima, P.; Anzai, J.-i.; Osa, T.; Bobbitt, J. M. Chem. Lett. 1996, 1043-4.
7. (d) Kashiwagi, Y.; Yanagisawa, Y.; Kurashima, F.; Anzai, J.; Osa, T.; Bobbitt, J. M. Chem. Commun. 1996, 2745-6.
8. (a) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Gautier-Luneau, I.; Pierre, J. L. J. Org. Chem. 1997, 62, 9385-7.
9. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Durif, A.; Averbunch, M.-T.; Pierre, J.-L. Tetrahedron Lett. 1998, 39, 2565-8.
10. Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 67, 1194-5.
11. Rychnovsky, S. D.; Beauchamp, T.; Vaidyanathan, R.; Kwan, T. J. Org. Chem. 1998, 63, 6363-74.
12. (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-62.
13. (b) Anelli, P. L.; Banfi, S.; Montanari, F.; Quici, S. J. Org. Chem. 1989, 54, 2970-2.
14. (c) Anelli, P. L.; Montanari, F.; Quici, S. Org. Synth. 1990, 69, 212-9.
15. (a) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J. L. J. Org. Chem. 1966, 61, 7452-4.
16. (b) DeMico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974-7.
17. Zhao, M. Z.; Li, J.; Mano, E.; Song, Z. G.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564-6.
18. Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A. Tetrahedron Lett. 1986, 27, 1119-22.
19. Golubev, V. A.; Borislaskii, E. G.; Aleksandrov, A. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1977, 26, 1874-81.
20. (a) Ma, Z.; Bobbitt, J. M. J. Org. Chem. 1991, 56, 6110-14.
21. (b) Kishioka, S.-y.; Ohki, S.; Ohsaka, T.; Tokuda, K. J. Electroanal. Chem. 1998, 452, 179-86.
22. Anatore, C. Principles and Methods. Basic Concepts. In Organic Electrochemistry; Baizer, M., Lund, H., Eds.; M.Dekker: New York, 1991; Chapter 2, pp 11-119.
23. Bobbitt, J. M.; Flores, M. C. L. Heterocycles 1988, 27, 509-533.
24. Compounds 13 and 14 lead to partial oxidation of sec-phenethyl alcohol, but the reaction was not reproducible and these nitroxides were not effective catalysts for 2-octanol. However, 13 did catalyze the oxidation of 1-octanol, suggesting that the inability of 13 to catalyze the oxidation of aliphatic secondary alcohols may be due in part to the degree of steric hindrance around the nitroxide function.
25. Lee, G. A.; Freedman, H. H. Tetrahedron Lett. 1976, 20, 1641-1644.
26. Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310-312.
27. Volodarsky, L. B.; Reznikov, V. A.; Ovcharenko, V. I. Synthetic Chemistry of Stable Nitroxides; CRC Press: Ann Arbor, MI, 1994.
28. Shchukin, G. I.; Ryabinin, V. A.; Grigor'ev, I. A.; Volodarsky, L. B. Zh. Obshch. Khim. 1988, 56, 855-860.
29. (a) Wayner, D. D. M.; Sim, B. A. J. Org. Chem. 1991, 56, 4853-4858.
30. (b) Workentin, M. S.; Wayner, D. D. M. Res. Chem. Intermed. 1993, 19, 777-785.
31. Brewster, M. E.; Huang, M.-J.; Kaminski, J. J.; Pop, E.; Bodor, N. J. Comput. Chem. 1991, 12, 1278-1282.
32. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
33. Wavefunction, Inc. 18401 Von Karman Ave., Suite 370, Irvine, CA 92612.
34. (a) Cramer, C. J.; Truhlar, D. G. J. Computer-Aided Mol. Des. 1992, 6, 629-666.
35. (b) Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 1991, 773, 8305-8311.
36. The best fit line gave the oxidation potential in mV as 34.78-[SM2 energy difference in kcal/mol] + 4164.
37. Cella, J. A.; Kelley, J. A.; Kenehan, E. F. Tetrahedron Lett. 1975, 33, 2869-72.