Publication Cover
Redox Report
Communications in Free Radical Research
Volume 1, 1995 - Issue 2
2
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Aerial oxidation of a redox-active porphyrin in the presence of a spin trap

, &
Pages 145-150 | Published online: 13 Jul 2016

References

  • This is part 17 of a series of papers under the general heading of ‘Facile aerial oxidation of porphyrins.’ Milgrom L R, Hill J P, Flitter W D. Facile aerial oxidation of porphyrins, part 16. Phenolic porphyrins without t-butyl substituents. J Chem Soc Perkin Trans 1994; 2: 521–524.
  • Fajer J, Davis M S. Electron spin resonance of porphyrin pi cations and anions. In: Dolphin D, ed. The porphyrins. New York: Academic Press, 1979; 4: 197–256.
  • Fajer J, Borg D C, Forman A, Dolphin D, Felton R H. Pi-cation radicals and dications of metalloporphyrins. J Am Chem Soc 1970; 92: 3451–3459.
  • Unsymmetrically meso-substituted porphyrins have slightly different spin-densities on the central nitrogens, see Atamian M, Wagner, R W, Lindsey, J S, Bocian, D F. Spin-density distributions in meso-alkyl/aryl hybrid porphyrin cation radicals. Inorg Chem 1988; 27: 1510–1512.
  • Milgrom L R, Jones C C, Harriman A. Facile aerial oxidation of a porphyrin part 3. Some metal complexes of meso-tetrakis(3,5-dit-butyl-4-hydroxyphenyl)porphyrin. J Chem Soc Perkin Trans 1988; 2: 71–79.
  • Milgrom L R, Flitter W D. Facile aerial oxidation of a porphyrin part 8. Decay of radical formed during the aerial oxidation of meso-tetrakis(3,5-di-t-butyl-4-hydroxyphenyl) porphyrin. Tetrahedron 1991; 47: 7683–7688.
  • Milgrom L R, Flitter W D, Short E L. Pi-cation radical generation via aerial oxidation of a porphyrin. J Chem Soc Chem Commun 1991; 788–790.
  • Milgrom L R, Flitter W D. J Chem Soc Chem Commun 1991; 1492–1494.
  • Milgrom L R, Flitter W D. Facile aerial oxidation of a porphyrin, part 13. Generation of pi-cation radicals via acid addition to meso-tetrakis (3,5-di-t-butyl-4-hydroxyphenyl)-porphyrin. Tetrahedron 1993; 49: 507–514.
  • Roberts J L Jr, Morrison M M, Sawyer D T. Base-induced generation of superoxide ion and hydroxyl radical from hydrogen peroxide. J Am Chem Soc 1978; 100: 330–331.
  • Sawyer D T. Oxygen chemistry. Oxford University Press, 1991.
  • Milgrom L R, Hill J P, Flitter W D. Formation of hydroxyl radicals during the facile aerial oxidation of a phenolic porphyrin. J Chem Soc Chem Commun 1992; 773–775.
  • Janzen E G. A critical review of spin trapping in biological systems. In: Pryor W A, ed. Free radicals in biology. New York: Academic Press, 1980; 4: 115–154.
  • Milgrom L R, Hill J P, Bone S. Evidence for solid state electronic conductivity in mixtures of a porphyrin and its two-electron oxidation product. Adv Mats Opt Electron 1993; 2: 143–147.
  • Stochi E. In: Stochi E, ed. Industrial chemistry. Ellis Harwood, 1990: ch. 5.
  • Albery W J, Bartlett P N, Jones C C, Milgrom L R. Facile aerial oxidation of a porphyrin, part 2. meso-tetrakis(3,4,5-trihydroxyphenyl)porphyrin. J Chem Res (M) 1985; 3810–3814:(S) 1985; 364–365.
  • Milgrom L R. The facile aerial oxidation of a porphyrin. Tetrahedron 1983; 39: 3895–3898.
  • Adler A D, Longo F, Finarelli J, Goldmacher J, Assour J, Korsakoff L. A simplified synthesis of meso-tetraphenylporphin J Org Chem 1967; 32: 476.
  • Weil J A, Anderson J K. The determination and reaction of 2,2′-diphenyl-1-picrylhydrazyl with thiosalicylic acid. J Chem Soc 1965; 5567–5570; Williams D E. Crystallographic data for 2,2′diphenyl-1-picrylhydrazyl. J Chem Soc 1965; 7535–7536.
  • Milgrom L R. Synthesis of some new tetraaryl porphyrins for studies in solar-energy conversion. J Chem Soc Perkin Trans 1983; 1: 2535–2539.
  • Carrington A, McLachlan A D. Introduction to magnetic resonance. New York: Harper and Row, 1969.
  • Neta P, Richoux M-C, Harriman A, Milgrom, L R. Resonance stabilisation of zinc porphyrin pi-radical cations. J Chem Soc Faraday 1986; 82: 209.
  • White W W. Aggregation of porphyrins and metallo-porphyrins. In: Dolphin D, ed. The porphyrins. New York: Academic Press, 1979; 5: 303–339.
  • Li A S W, deHaas A H, Buettner G R, Chignall C F. A database for spin-trapping implemented on the IBM PC/AT. J Magn Reson 1988; 79: 140–142.
  • Rosen G M, Rauckman E J. Spin-trapping of free radicals during hepatic microsomal lipid peroxidation. Proc Natl Acad Sci USA 1981; 78: 7346–7349.
  • Huysmans W G B, Waters W A. Aryloxy-radicals, part 6. Measurement of the electron spin resonance spectra of short-lived phenoxy-radicals in benzene solutions. J Chem Soc 1966; 1047–1049.
  • Albery W J, Bartlett P N, Jones C C, Milgrom L R. Facile aerial oxidation of a porphyrin, part 2. Tetrakis[meso-3,4,5-trihydroxyphenyl)]porphyrin. J Chem Res (S) 1985; 364–365: (M) 1985; 3801–3814.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.