Antioxidant activities of vitamin E analogues in water and a Kamlet-Taft β-value for water

Journal of the American Chemical Society

Volumn 118, Issue 15, 1996, Pages

  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: 5244374639     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (67)

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5. 9
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28. 27 The smaller antioxidant activity in protic solvents was attributed to hydrogen bonding. Unfortunately, these are only rate constant ratios and it appears unlikely to us that this ratio should, e.g., be greater in acetonitrile than in hexane.
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32. For some interesting observations and discussions regarding the inhibition of peroxidation of phospholipid bilayers by water-soluble α-TOH analogues and their partitioning between the bilayer and the water, see: Barclay, L. R C , Vinqvist, M. R Free Radical Biol. Med. 1994, 16, 779-788. Barclay, L. R. C.; Artz, J. D.; Mowat, J. J. Biochim. Biophys. Acta 1995, 1237, 77-85.
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44. See, e.g.; Hilborn, J. W.; Pincock, J. A. J. Am. Chem. Soc. 1991, 113, 3683-2686.
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46. Abraham, M H.; Greiller, P. L.; Prior, D. V ; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1990, 521-529. See also: Abraham, M. H.; Grellier, P. L., Prior, D. V.; Taft, R W.; Morris, J. J ; Taylor, P. J.; Laurence, C.; Berthelot, M.; Doherty, R. M.; Kamlet, M. J.; Abboud, J.-L. M.; Sraidi, K.; Guihéneuf, G. J Am. Chem. Soc. 1988, 110, 8534-8536. Abraham, M. H.; Grellier, P. L., Prior, D V.; Morris, J. J.; Taylor, P. J. Tetrahedron Lett. 1989, 30, 2571-2574 Laurence, C.; Berthelot, M.; Helbert, M.; Sraidi, K. J. Phys. Chem. 1989, 93, 3799-3802. Abraham, M. H.; Lieb, W. R., Franks, N. P. J. Pharm. Sci. 1991, 80, 719-724.
47. Abraham, M H.; Greiller, P. L.; Prior, D. V ; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1990, 521-529. See also: Abraham, M. H.; Grellier, P. L., Prior, D. V.; Taft, R W.; Morris, J. J ; Taylor, P. J.; Laurence, C.; Berthelot, M.; Doherty, R. M.; Kamlet, M. J.; Abboud, J.-L. M.; Sraidi, K.; Guihéneuf, G. J Am. Chem. Soc. 1988, 110, 8534-8536. Abraham, M. H.; Grellier, P. L., Prior, D V.; Morris, J. J.; Taylor, P. J. Tetrahedron Lett. 1989, 30, 2571-2574 Laurence, C.; Berthelot, M.; Helbert, M.; Sraidi, K. J. Phys. Chem. 1989, 93, 3799-3802. Abraham, M. H.; Lieb, W. R., Franks, N. P. J. Pharm. Sci. 1991, 80, 719-724.
48. Abraham, M H.; Greiller, P. L.; Prior, D. V ; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1990, 521-529. See also: Abraham, M. H.; Grellier, P. L., Prior, D. V.; Taft, R W.; Morris, J. J ; Taylor, P. J.; Laurence, C.; Berthelot, M.; Doherty, R. M.; Kamlet, M. J.; Abboud, J.-L. M.; Sraidi, K.; Guihéneuf, G. J Am. Chem. Soc. 1988, 110, 8534-8536. Abraham, M. H.; Grellier, P. L., Prior, D V.; Morris, J. J.; Taylor, P. J. Tetrahedron Lett. 1989, 30, 2571-2574 Laurence, C.; Berthelot, M.; Helbert, M.; Sraidi, K. J. Phys. Chem. 1989, 93, 3799-3802. Abraham, M. H.; Lieb, W. R., Franks, N. P. J. Pharm. Sci. 1991, 80, 719-724.
49. Abraham, M H.; Greiller, P. L.; Prior, D. V ; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1990, 521-529. See also: Abraham, M. H.; Grellier, P. L., Prior, D. V.; Taft, R W.; Morris, J. J ; Taylor, P. J.; Laurence, C.; Berthelot, M.; Doherty, R. M.; Kamlet, M. J.; Abboud, J.-L. M.; Sraidi, K.; Guihéneuf, G. J Am. Chem. Soc. 1988, 110, 8534-8536. Abraham, M. H.; Grellier, P. L., Prior, D V.; Morris, J. J.; Taylor, P. J. Tetrahedron Lett. 1989, 30, 2571-2574 Laurence, C.; Berthelot, M.; Helbert, M.; Sraidi, K. J. Phys. Chem. 1989, 93, 3799-3802. Abraham, M. H.; Lieb, W. R., Franks, N. P. J. Pharm. Sci. 1991, 80, 719-724.
50. Abraham, M H.; Greiller, P. L.; Prior, D. V ; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1990, 521-529. See also: Abraham, M. H.; Grellier, P. L., Prior, D. V.; Taft, R W.; Morris, J. J ; Taylor, P. J.; Laurence, C.; Berthelot, M.; Doherty, R. M.; Kamlet, M. J.; Abboud, J.-L. M.; Sraidi, K.; Guihéneuf, G. J Am. Chem. Soc. 1988, 110, 8534-8536. Abraham, M. H.; Grellier, P. L., Prior, D V.; Morris, J. J.; Taylor, P. J. Tetrahedron Lett. 1989, 30, 2571-2574 Laurence, C.; Berthelot, M.; Helbert, M.; Sraidi, K. J. Phys. Chem. 1989, 93, 3799-3802. Abraham, M. H.; Lieb, W. R., Franks, N. P. J. Pharm. Sci. 1991, 80, 719-724.
51. Kamlet, M. J.; Abboud, J. L.; Abraham, M. H., Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887 and references cited therein. See also, Marcus, Y.; Kamlet, M J., Taft, R. W J. Phys. Chem. 1988, 92, 3613-3622.
52. Kamlet, M. J.; Abboud, J. L.; Abraham, M. H., Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887 and references cited therein. See also, Marcus, Y.; Kamlet, M J., Taft, R. W J. Phys. Chem. 1988, 92, 3613-3622.
53. This plot therefore excludes the points for acetic acid (no β value), tert-butyl alcohol (a non-reliable β = 1.01), and water (a non-reliable β = 0.18).
54. 2 value for tert-butyl alcohol is 0.49.
55. 45
56. Valgimigli, L. Unpublished results.
57. Avila, D. V., Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466-470.
58. 9b 21 23
59. 45
60. Wayner, D. D. M ; Lusztyk, E.. Pagé, D.; Ingold, K. U ; Mulder, P ; Laarhoven, L. J. J., Aldrich, H S. J. Am Chem. Soc. 1995, 117, 8737-8744.
61. Charton, M. Prog. Phys. Org. Chem. 1981, 13, 119-251.
62. Intramolecular hydrogen bonding between the C(O)OH group and the ring oxygen atom may also affect the reactivities of the carboxylic acids, see ref 4.
63. 40 not 0.00 as given in ref 36c.
64. The IUPAC name for this compound is 3-[(tert-butyldioxy)carbonyl]-propionic acid.
65. Artym, I. I.; Ivanchev, M. M.; Soltys, M. M.; Kovbuz, M. A. Zh. Prikl. Khim. 1976, 49, 2056-2059 (Engl. transl.).
66. Davies, A. G.; Foster, R. V.; White, A. M. J. Chem. Soc. 1953, 1541-1547.
67. Kazanis, S.; Azarani, A.; Johnston, L J. J. Phys. Chem. 1991, 95, 4430-4435.