Solvent effects on the reactivity and free spin distribution of 2,2-diphenyl-1-picrylhydrazyl radicals

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7947-7950

  Valgimigli, Luca ^a,b   Ingold, K U ^a   Lusztyk, J ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000729874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9608578     Document Type: Article

References (31)

1. Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466-470.
2. Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Green, W. H.; Procopio, D. R. J. Am. Chem. Soc. 1995, 117, 2929-2930.
3. Additional KSE data on reaction 2 can be found in references 6 and 7.
4. Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 9966-9971.
5. MacFaul, P. A.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1996, 61, 1316-1321.
6. 6
7. Shared to a lesser extent by n-butanol and 2-propanol, vide infra.
8. Goldschmidt, S.; Renn, K. Berichte 1922, 55, 628-643.
9. Hutchinson, C. A., Jr.; Pastor, R. C.; Kowalsky, A. G. J. Chem. Phys., 1952, 20, 534-535. In this study only the averaged hfcc of the two central nitrogen atoms was observed. The first report of the inequality of these two nitrogen hfcc's is: Deal, R. M.; Koski, W. S. J. Chem. Phys. 1959, 31, 1138-1139.
10. Hutchinson, C. A., Jr.; Pastor, R. C.; Kowalsky, A. G. J. Chem. Phys., 1952, 20, 534-535. In this study only the averaged hfcc of the two central nitrogen atoms was observed. The first report of the inequality of these two nitrogen hfcc's is: Deal, R. M.; Koski, W. S. J. Chem. Phys. 1959, 31, 1138-1139.
11. Holmberg, R. W.; Livingston, R.; Smith, W. T., Jr. J. Chem. Phys. 1960, 33, 541-546. Gamo, K.; Masuda, K.; Yamaguchi, J.; Kakitani, T. J. Phys. Soc. Jpn. 1965, 20, 1730. Gubanov, V. A.; Koriakov, V. I.; Chirkov, A. K. J. Magn. Reson. 1973, 9, 263-274.
12. Holmberg, R. W.; Livingston, R.; Smith, W. T., Jr. J. Chem. Phys. 1960, 33, 541-546. Gamo, K.; Masuda, K.; Yamaguchi, J.; Kakitani, T. J. Phys. Soc. Jpn. 1965, 20, 1730. Gubanov, V. A.; Koriakov, V. I.; Chirkov, A. K. J. Magn. Reson. 1973, 9, 263-274.
13. Holmberg, R. W.; Livingston, R.; Smith, W. T., Jr. J. Chem. Phys. 1960, 33, 541-546. Gamo, K.; Masuda, K.; Yamaguchi, J.; Kakitani, T. J. Phys. Soc. Jpn. 1965, 20, 1730. Gubanov, V. A.; Koriakov, V. I.; Chirkov, A. K. J. Magn. Reson. 1973, 9, 263-274.
14. Chen, M. M.; Sane, K. V.; Walter, R. I.; Weil, J. A. J. Phys. Chem. 1961, 65, 713-717. Hyde, J. S.; Sneed, R. C., Jr.; Rist, G. H. J. Chem. Phys. 1969, 51, 1404-1416. Gubanov, V. A.; Koryakov, V. I.; Chirkov, A. K. J. Magn. Reson. 1973, 11, 326-334. Dalal, N. S.; Kennedy, D. E.; McDowell, C. A. J. Chem. Phys. 1973, 59, 3403-3410. Biehl, R.; Möbius, K.; O'Connor, S. E.; Walter, R. I.; Zimmermann, H. J. Phys. Chem. 1979, 83, 3449-3456.
15. Chen, M. M.; Sane, K. V.; Walter, R. I.; Weil, J. A. J. Phys. Chem. 1961, 65, 713-717. Hyde, J. S.; Sneed, R. C., Jr.; Rist, G. H. J. Chem. Phys. 1969, 51, 1404-1416. Gubanov, V. A.; Koryakov, V. I.; Chirkov, A. K. J. Magn. Reson. 1973, 11, 326-334. Dalal, N. S.; Kennedy, D. E.; McDowell, C. A. J. Chem. Phys. 1973, 59, 3403-3410. Biehl, R.; Möbius, K.; O'Connor, S. E.; Walter, R. I.; Zimmermann, H. J. Phys. Chem. 1979, 83, 3449-3456.
16. Chen, M. M.; Sane, K. V.; Walter, R. I.; Weil, J. A. J. Phys. Chem. 1961, 65, 713-717. Hyde, J. S.; Sneed, R. C., Jr.; Rist, G. H. J. Chem. Phys. 1969, 51, 1404-1416. Gubanov, V. A.; Koryakov, V. I.; Chirkov, A. K. J. Magn. Reson. 1973, 11, 326-334. Dalal, N. S.; Kennedy, D. E.; McDowell, C. A. J. Chem. Phys. 1973, 59, 3403-3410. Biehl, R.; Möbius, K.; O'Connor, S. E.; Walter, R. I.; Zimmermann, H. J. Phys. Chem. 1979, 83, 3449-3456.
17. Chen, M. M.; Sane, K. V.; Walter, R. I.; Weil, J. A. J. Phys. Chem. 1961, 65, 713-717. Hyde, J. S.; Sneed, R. C., Jr.; Rist, G. H. J. Chem. Phys. 1969, 51, 1404-1416. Gubanov, V. A.; Koryakov, V. I.; Chirkov, A. K. J. Magn. Reson. 1973, 11, 326-334. Dalal, N. S.; Kennedy, D. E.; McDowell, C. A. J. Chem. Phys. 1973, 59, 3403-3410. Biehl, R.; Möbius, K.; O'Connor, S. E.; Walter, R. I.; Zimmermann, H. J. Phys. Chem. 1979, 83, 3449-3456.
18. Chen, M. M.; Sane, K. V.; Walter, R. I.; Weil, J. A. J. Phys. Chem. 1961, 65, 713-717. Hyde, J. S.; Sneed, R. C., Jr.; Rist, G. H. J. Chem. Phys. 1969, 51, 1404-1416. Gubanov, V. A.; Koryakov, V. I.; Chirkov, A. K. J. Magn. Reson. 1973, 11, 326-334. Dalal, N. S.; Kennedy, D. E.; McDowell, C. A. J. Chem. Phys. 1973, 59, 3403-3410. Biehl, R.; Möbius, K.; O'Connor, S. E.; Walter, R. I.; Zimmermann, H. J. Phys. Chem. 1979, 83, 3449-3456.
19. Garifyanov, N. S.; Il'yasov, A. V.; Yablokov, Yu. V. Dokl. Akad. Nauk SSSR 1963, 149, 876-879. English translation, pp 280-283.
20. -1 at 50°C.
21. Hogg, J. S.; Lohmann, D. H.; Russell, K. E. Can. J. Chem. 1961, 39, 1394-1396.
22. . and a solvent molecule, and these effects were correlated with the ionization potential (IP) of the solvent. Unfortunately, there are no tabulated data in this publication, and the correlation is only shown graphically with the solvents not identified.
23. Ryzhmanov, Yu. M.; Egorova, A. A. Dokl. Akad. Nauk SSSR 1970, 191, 148-150. English translation, pp 227-229.
24. (a) Knauer, B. R.; Napier, J. J. J. Am. Chem. Soc. 1976, 98, 4395-4400.
25. (b) Reddock, A. H.; Konishi, S. J. Chem. Phys. 1979, 70, 2121-2130.
26. 17a but was estimated from data for di-tert-butyl nitroxide, see footnote f to Table IV of reference 21.
27. Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983-4992.
28. 3CN and t-BuOH) in the other solvents.
29. Chen, M. M.; D'Adamo, A. F. Jr.; Walter, R. I. J. Org. Chem. 1961, 26, 2721-2727.
30. O'Connor, S. E.; Walter, R. I. J. Org. Chem. 1977, 42, 577-578.
31. Poirier, R. H.; Benington, F. J. Am. Chem. Soc. 1952, 74, 3192.