Redox behaviour of phenolic porphyrins in basic solutions: A reappraisal

Free Radical Research

Volumn 24, Issue 1, 1996, Pages 19-29

  Milgrom, Lionel R ^a   Yahioglu, Gokhan ^a   Jogiya, Neha N ^a  

^a BRUNEL UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI; FREE RADICAL; PHENOL DERIVATIVE; PHENOXYL RADICAL; PORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION; SOLUTION AND SOLUBILITY; SPECTROPHOTOMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

ALKALIES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENOLS; PORPHYRINS; SOLUTIONS; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0029690569     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.3109/10715769609087996     Document Type: Article

References (22)

1. This paper is part 20 in a series entitled "Facile Aerial Oxidation of Porphyrins". Part 19 is L.R. Milgrom, J.P. Hill, and P.J.F. Dempsey (1994) Alkylation of 5,10,15-tris(3,5-di-t-butyl-4-hydroxyphenyl)-20-(4-pyridyl) porphyrin. Tetrahedron, 50, 13477-13484.
2. See L.R. Milgrom, J.P. Hill, and W.D. Flitter (1994) Facile Aerial Oxidation of Porphyrins. Part 16. Phenolic porphyrins without t-butyl substituents. Journal of the Chemical Society, Perkin Transactions 2. 521-524, and references therein.
3. L.R. Milgrom (1983) The facile aerial oxidation of a porphyrin. Tetrahedron, 39, 3895-3898.
4. L.R. Milgrom and W.D. Flitter (1991) Improved generation of porphyrin radicals via conproportionation. Journal of the Chemical. Society, Chemical Communications, 1492-1494.
5. L.R. Milgrom, J.P. Hill, and W.D. Flitter (1992). Formation of hydroxyl radicals during the facile aerial oxidation of a phenolic porphyrin. Journal of the Chemical Society, Chemical Communications, 773-775.
6. W.J. Albery, P.N. Bartlett, C.C. Jones, and L.R. Milgrom (1985). Facile aerial oxidation of a porphyrin. Part 2. Mesotetrakis(3,4,5-trihydroxyphenyl)porphyrin. Journal of Chemical Research. (S) 364-365; (M) 3801-3814.
7. L.R. Milgrom, G. Yahioglu, and W.D. Flitter (1994) Aerial oxidation of a redox-active porphyrin in the presence of a spin-trap. Redox Report, 1, 145-150.
8. See J.A. Weil and J.K. Anderson (1965) The determination and reaction of 2,2-diphenyl-1-picrylhydrazyl with thiosalicylic acid, Journal of the Chemical Society, 5567-5570.
9. D.E. Williams (1965) Crystallographic data for 2,2-diphenyl-1-picrylhydrazyl. Journul of the Chemical Society, 7535-7536.
10. a, L.R. Milgrom, C.C. Jones and A. Harriman (1988) Facile aerial oxidation of a porphyrin. Part 3. Some metal complexes of meso-tetrakis(3,5-di-t-butyl-4-hydroxyphenyl) porphyrin, Journal of the. Chemical Society, Perkin Transactions 2. 71-79:
11. b, A.J. Golder, L.R. Milgrom, K.B. Nolan, and D.C. Povey (1989) 5,10,15,20-Misotetrakis(3,5-di-t-butyl-4-quinomethide)porphyrinogen: a highly puckered tetrapyrrolic macrocycle from the facile aerial oxidation of a phenolic porphyrin. Journal of the Chemical Society, Chemical Communications, 1751-1753:
12. c, H. Scheer and H.H. Inhoffen (1978) Hydroporphyrins: reactivity, spectroscopy, and hydroporphyrin analogues in The Porphyrins (ed. D. Dolphin), Academic Press, London and New York, pp. 45-90.
13. L.R. Milgrom, N. Mofidi, C.C. Jones and A. Harriman (1989) Facile aerial oxidation of a porphyrin. Part 4. Unsymmetrical meso-tetraarylporphyrins with 3,5-di-t-butyl-4-hydroxyphenyl and 4-hydroxyphenyl substituents. Journal of the Chemical Society Perkin Transactions 2, 301-309.
14. That porphyrins 1, 4, and 5 give esr spectra in deoxygenated as well as undegassed basic solutions, contradicts earlier reports (see references 2 and 7). An intermittant, non-reproducable, fault (now rectified) in the field-set potentiometer of the Varian instrument was found to be the apparent source of this contradiction.
15. a, J.L. Roberts, Jr., H. Sugimoto, W.C. Barette, Jr., and D.T. Sawyer (1985) One-electron reduction of anthraquinone by hydroxide ion in aprotic media. Journal of the American Chemical Society, 107, 4556-4557:
16. b, D.T. Sawyer (1991) Oxygen Chemistry, Oxford University Press, New York and Oxford, p. 201.
17. J.L. Roberts, Jr., M.M. Morrison and D.T. Sawyer (1978) Base-induced generation of superoxide ion and hydroxyl radical from hydrogen peroxide. Journal of the American Chemical Society, 100, 329-330.
18. L.R. Milgrom and W.D. Flitter (1992) Facile aerial oxidation of a porphyrin. Part 12. Spin-trapping of solventderived intermediates from the addition of base to an oxidised porphyrin. Tetrahedron, 48, 2951-2956.
19. H. Scheer (1978) Synthesis and stereochemistry of hydroporphyrins in The Porphyrins (ed. D. Dolphin), Academic Press, London and New York, pp. 1-44.
20. H.W. Moore and R.J. Wikholm (1974) Rearrangements of quinones in The Chemistry of Quinonoid Compounds (ed. S. Patai), John Wiley & Sons, London, pp. 441-446.
21. The zinc complex of porphyrin 1 has been shown to catalyse the two-electron reduction of dioxygen: T.A. Evans, G.S. Srivatsa, D.T. Sawyer and T.G. Traylor (1985) Redox chemistry of tetrakis(3,5-di-terf-butyl-4-hydroxyphenyl) porphine an its zinc(II) complex in dimethylformamide. Inorganic Chemistry, 24, 4733-4735.
22. 12: experiments concerning the origin of its molecular structure. Angewandte Chemie, International Edition, (English) 27, 5-39.