Comparison of diffusion coefficients of aryl carbonyls and aryl alcohols in hydroxylic solvents. Evidence that the diffusion of ketyl radicals in hydrogen-bonding solvents is not anomalous?

Journal of Physical Chemistry A

Volumn 105, Issue 24, 2001, Pages 5948-5953

  Autrey, Tom ^a   Kandanarachchi, Pramod ^a   Franz, James A ^a  

^a PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL CARBONYLS;

DIFFUSION; FREE RADICALS; HYDROGEN BONDS; ORGANIC SOLVENTS;

AROMATIC COMPOUNDS;

EID: 0035927417     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp004291+     Document Type: Review

References (46)

1. Huang, Y.; Page, D.; Wayner, D. D. M.; Mulder, P. Can. J. Chem. 1995, 73, 2079.
2. Scaiano, J. C.; Netto-Ferreira, J. C.; Wintgens, V. J. Photochem. Photobiol. A: Chem. 1991, 59, 265.
3. Autrey, S. T.; Alnajjar, M. S.; Nelson, D. A.; Franz, J. A. J. Org. Chem. 1991, 56, 2197.
4. Franz, J. A.; Bushaw, B. A.; Alnajjar, M. S. J. Am. Chem. Soc. 1989, 111, 268.
5. Franz, J. A.; Linehan, J. C.; Birnbaum, J. C.; Hicks, K. W.; Alnajjar, M. S. J. Am. Chem. Soc. 1999, 121, 9824.
6. Okamoto, K.; Hirota, N.; Terazima, M. J. Phys. Chem. A 1997, 101, 5269.
7. Donkers, R. L.; Leaist, D. G. J. Phys. Chem. B 1997, 101, 304.
8. Saltiel, J. A.; Atwater, B. W. Advances in Photochemistry; Wiley-Interscience: New York, 1988, Vol. 14.
9. Lehni, M.; Fischer, H. Int. J. Chem. Kinetics 1983, 15, 733.
10. Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200.
11. Schuh, H.-H.; Fischer, H. Helvetica Chimica Acta 1978, 61, 2130.
12. Huggenberger, C.; Lipscher, J.; Fischer, H. J. Phys. Chem. 1980, 84, 3467.
13. Munger, K.; Fischer, H. Int. J. Chem. Kinet. 1984, 16, 1213.
14. Okamoto, K.; Hirota, N.; Terazima, M. J. Phys. Chem. 1997, 101, 5380.
15. Terazima, M. Res. Chem. Intermed. 1997, 23, 853.
16. Terazima, M ; Tenma, S ; Watanabe, H.; Tominaga, T. J. Chem. Soc., Faraday Trans. 1996, 92, 3057.
17. Terazima, M. Acc. Chem. Res. 2000, 33, 687.
18. Terazima, M.; Okamoto, K.; Hirota, N. J. Chem. Phys. 1995, 102, 2506.
19. Morita, A ; Kato, S. J. Chem. Phys. 1998, 108, 6809.
20. Morita, A.; Kato, S. J. Am. Chem. Soc. 1997, 119, 4021.
21. Biswas, R.; Bhattacharyya, S.; Bagchi, B. J. Phys. Chem. B. 1998, 102, 3252.
22. Tominaga, T.; Tenma, S.; Watanabe, H. J. Chem. Soc., Faraday Trans. 1996, 92, 1863.
23. Chan, M. L.; Chan, T. C. J. Phys. Chem. 1995, 99, 5765.
24. Taylor, S. G. Proc. R. Soc. London A 1953, 219, 186.
25. Terazima, M.; Okamoto, K.; Hirota, N. J. Phys. Chem. 1993, 97, 13 387.
26. Wilke. C. R.; Chang, P. A. I. Ch. E. J. 1955, June, 264.
27. Spernol, V. A.; Wirtz, K. Naturforsch. A 1953, 8, 522.
28. Wagner, P. J. Acc. Chem. Res. 1989, 22, 83.
29. Wagner, P. J.; Giri, B. P.; Scaiano, J. C.; Ward, D. L.; Gabe, E ; Lee, F. L. J. Am. Chem. Soc. 1985, 107, 5483.
30. Wagner, P. J. Acc. Chem. Res. 1971, 4, 168.
31. Wagner, P. J. J. Am. Chem. Soc. 1967, 89, 5898.
32. Scaiano, J. C. Acc. Che. Res 1982, 15, 252.
33. Caldwell, R. A.; Majima, T.; Pac, C. J. Am. Chem. Soc. 1982, 104, 629.
34. Kanabus-Kaminska, J. M.; Gilbert, B. C.; Griller, D. J. Am. Chem. Soc. 1989, 111, 3311.
35. Laarhoven, L. J. J.; Mulder, P.; Wayner, D. D. M. Acc. Chem. Res. 1999, 32, 342.
36. Pratt, K. C.; Wakeham, W. A. Proc. R. Soc. London A 1975, 342, 401.
37. Pratt, K. C.; Wakeham, W. A. J. Chem Soc., Faraday Trans. 2 1977, 73, 997.
38. Alnajjar, M. S.; Garrossian, M. S.; Autrey, S. T.; Ferris, K. F.; Franz, J. A. J. Phys. Chem. 1992, 96, 7037.
39. This method of measuring the ID of the tubing is preferrable to using the manufacture stated ID. When we used the ID specified by the manufacturer, we obtained lower diffusion coefficient values. With our experimental measured ID, we obtained good agreement for the ketone diffusion coefficients with the values reported by Donkers and Leaist in ref 7. We thank a referee for pointing this out.
40. Reid, R. C.; Prausnitz, J. M.; Sherwood, T. K. The Properties of Gases and Liquids, 3rd ed.; McGraw-Hill: New York, 1977.
41. The transient grating measurements of a few representive radicals have recently be adjusted upwards between 7 and 17%.
42. Deno, N. C.; Wisotsky; Max, J. J. Am. Chem. Soc. 1963, 85, 1735.
43. Hayon, E.; Ibata, T.; Lichtin, N. N.; Simic, M. J. Phys. Chem. 1972, 76, 2072.
44. Stewart, R. Organic Chemistry; Academic Press: New York, 1985; Vol. 46.
45. b is 1 for nonassociating solvents, 1.5 for ethanol, and ca. 1.7 for 2-propanol.
46. Gainer, J. L.; Metzner, A. B. A. I. Ch. E.-I. Chem. E. 1965, Symposium Series No. 6, 74.