Radiolytic generation and photochemistry of 9-xanthenyl radicals in halogenated solvents

Radiation Physics and Chemistry

Volumn 57, Issue 2, 2000, Pages 157-165

  Sumiyoshi, Takashi ^a   Ueta, Shohei ^a   Wu, Feng ^a   Sawamura, Sadashi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHLOROETHANE; BENZOPHENONE; CARBON TETRACHLORIDE; HALOCARBON; NAPHTHALENE; OXYGEN; PEROXY RADICAL; RADICAL; SOLVENT; XANTHENE;

ARTICLE; BLEACHING; IN VITRO STUDY; LASER; PHOTOCHEMISTRY; PHOTOLYSIS; PULSE RADIOLYSIS; REACTION ANALYSIS;

DISSOCIATION; ORGANIC SOLVENTS; OXYGEN; PHOTOLYSIS; PULSED LASER APPLICATIONS;

LASER FLASH PHOTOLYSIS; PHOTOBLEACHING; PULSE RADIOLYSIS; QUANTUM YIELDS; XANTHENYL;

AROMATIC COMPOUNDS;

EID: 0033622854     PISSN: 0969806X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-806X(99)00350-3     Document Type: Article

References (44)

1. Arai S., Ueda H., Firestone R.F., Dorfman L.M. Pulse-radiolysis observation of molecular cations of aromatic compounds in halogenated liquids. J. Chem. Phys. 50:1969;1072.
2. Bensasson R., Land E.J. Triplet-triplet extinction coefficients via energy transfer. Trans. Faraday Soc. 67:1971;1904.
3. Bibler N.E. Dose rate effects in the steady and pulse radiolysis of liquid chloroform. J. Phys. Chem. 75:1971;2436.
4. Bromberg A., Schmidt K.H., Meisel D. Photophysics and photochemistry of arylmethyl radicals in liquids. J. Am. Chem. Soc. 107:1985;83.
5. Bühler R.E., Ebert M. Transient charge-transfer complexes with chlorine atoms by pulse radiolysis of carbon tetrachloride solutions. Nature (London). 214:1967;1220.
6. Clifton M.F., Fenick D.J., Gasper S.M., Falvey D.E., Boyd M.K. Photogeneration of the xanthyl cation: β-Cleavage from excited state ketones. J. Org. Chem. 59:1994;8023.
7. Ebbesen T.W., Akaba R., Tokumaru K., Washio S., Tagawa S., Tabata Y. Cis and trans olefin radicals: Equilibrium and photoisomerization. J. Am. Chem. Soc. 100:1988;2147.
8. Emmi S.S., Beggiato G., Casalbore-Miceli G. Transient species in the pulse radiolysis of methylene chloride and the self-reaction of chloromethyl radicals. Radiat. Phys. Chem. 33:1989;29.
9. Fielden E.M., Holm N.W. Dosimetry in accelerator research and processing. Holm N.M., Berry R.J. Manual on Radiation Dosimetry. 1970;261 Marcel Dekker, New York.
10. Huang C-G., Shukla D., Wan P. Mechanism of photosomerization of xanthene to 6-H-dibenzo[b,d]pyran in aqueous solution. J. Org. Chem. 56:1991;5437.
11. Ishida A., Yamamoto K., Takamuku S. Electron-laser dual beam irradiation of 2-methylbenzophenone. Bull. Chem. Soc. Jpn. 65:1992;3186.
12. Kny-Jones, F.G., Ward, A.M., 1930. Investigations on the bivalency of carbon. Part III. Some experiments on xanthhydrol, dixanthhydryl ether, and xanthhydryl chloride J. Chem. Soc. 535.
13. Lamola A.A., Hammond G.S. Mechanisms of photochemical reactions in solution. XXXIII. Intersystem crossing efficiencies. J. Chem. Phys. 43:1965;2129.
14. Lide D.R. CRC Handbook of Chemistry and Physics. 76th ed. 1995;CRC Press, Boca Raton.
15. Maillard B., Ingold K.U., Scaiano J.C. Rate constants for the reactions of free radicals with oxygen in solution. J. Am. Chem. Soc. 105:1983;5095.
16. Majima T., Fukui M., Ishida A., Takamuku S. Stilbene radical anions in the excited doublet state. J. Phys. Chem. 100:1996;8913.
17. Marcinek A., Rogowski J., Adamus J., Gebicki J., Platz M.S. Sequential electron-proton-electron transfer in the radiolytic and photochemical oxidation of thioxanthene and xanthene. J. Phys. Chem. 100:1996;13539.
18. Margenau H., Murphy G.M. The Mathematics of Physics and Chemistry. 1955;D Van Nostrand Co, New York.
19. Maruyama K., Arakawa S. Photochemistry of epoxyquinones. 1. Photochemical reactions of 2-alkyl-2,3-epoxy-2,3-dihydro-1,4-naphthoquinones with hydrogen donors. J. Org. Chem. 43:1977;3793.
20. Masuhara H., Okuda M., Koizumi M. Studies on the electronic spectra of the semiquinones of anthracene and its related heterocycles. I. Bull. Chem. Soc. Jpn. 41:1968;2319.
21. Mehnert R., Brede O., Bös J., Naumann W. Charge transfer from the carbon tetrachloride radical cation to alkyl chlorides, alkanes, alkenes and aromatics. Ber. Bunsenges. Phys. Chem. 83:1979;992.
22. Minto R.E., Das P.K. A laser flash photolysis study of photodehydroxylation phenomena of 9-phenylxanthene-9-ol and photobehavior of related intermediates. Enhanced electrophilicity of 9-phenylxanthenium cation singlet. J. Am. Chem. Soc. 111:1989;8858.
23. Mönig J., Bahnemann D., Asmus K-D. One electron reduction of carbon tetrachloride in oxygenated aqueous solutions: a trichloromethyldioxy-free radical mediated formation of chloride and carbon dioxide. Chem.-Biol. Interact. 47:1983;15.
24. Murov S.L., Carmichael I., Hug G.L. Handbook of Photochemistry. 2nd ed. 1993;Marcel Dekker, New York.
25. Natarajan P., Fessenden R.W. A study of the photoionization of anion radicals in aqueous solution. J. Phys. Chem. 93:1989;6095.
26. Raner K.D., Lusztyk J., Ingold K.U. Ultraviolet/visible spectra of halogen molecule/arene and halogen atom/arene π-molecular complexes. J. Phys. Chem. 93:1989;564.
27. Scaiano J.C., Tanner M., Weir D. Exploratory study of the intermolecular reactivity of excited diphenylmethyl radicals. J. Am. Chem. Soc. 107:1985;4396.
28. Schmidt J.A., Hilinski E.F. Evolution of electronically excited triphenylmethyl radical. Picosecond preparation-pump-probe spectroscopic experiments. J. Am. Chem. Soc. 110:1988;403.
29. Shida T. Electronic Absorption Spectra of Radical Ions. 1988;Elsevier, New York.
30. Spinks, J.W.T., Woods, R.J., 1990. An Introduction to Radiation Chemistry, 3rd ed. Wiley, New York.
31. Sumiyoshi T., Sawamura S., Koshikawa Y., Katayama M. Transient species in picosecond pulse radiolysis of liquid carbon tetrachloride. Bull. Chem. Soc. Jpn. 55:1982;2346.
32. Sumiyoshi, T., Miura, K., Hagiwara, H., Katayama, M., 1987. On the reactivity of chlorine atoms towards alcohols. Chem. Lett. 1429.
33. Sumiyoshi T., Sugita N., Watanabe K., Katayama M. Pulse radiolysis studies of solvent radical cations in liquid 1,2-dichloroethane. Bull. Chem. Soc. Jpn. 61:1988;3059.
34. Sumiyoshi T., Katayama M. Formation mechanism of the complexes between DMSO and halogen atoms. I. Pulse radiolysis studies. Bull. Chem. Soc. Jpn. 63:1990;1293.
35. Sumiyoshi, T., Sakai, H., Kawasaki, M., Katayama, M., 1992a. Pulse radiolysis-laser flash photolysis studies of diphenyl sulfide in liquid halocarbons. Chem. Lett. 617.
36. Sumiyoshi T., Katayama M. Reactivity of alcohols towards the chlorine atom in carbon tetrachloride. Trends Phys. Chem. 1:1992;7.
37. Sumiyoshi T., Kawasaki M., Katayama M. Photochemistry of diphenyl sulfide/halogen and mesitylene/halogen complexes in liquid halocarbons. Bull. Chem. Soc. Jpn. 66:1993;2510.
38. Sumiyoshi, T., Wu, F., Shindo, T., Ueta, S., Sawamura, S., 1997. Pulse radiolysis-laser flash photolysis study of xanthene in 1,2-dichloroethane/carbon tetrachloride. Chem. Lett. 1167.
39. Tanimoto Y., Takashima M., Itoh M. Magnetic field effect on the hydrogen abstraction of xanthone from xanthene in SDS micelles. Chem. Phys. Lett. 100:1983;442.
40. Tupikov V.I. Rate constants for the reactions of intermediates in the radiolysis of organic liquids. Milinchuk V.K., Tupikov V.I. Organic Radiation Chemistry Handbook. 1989;44 Ellis Horwood, Chichester.
41. Wang Y., Tria J.J., Dorfman L.M. Identity and yield of positive charge centers in irradiated chloro hydrocarbon liquids and the rates of their interaction with solute molecules. J. Phys. Chem. 83:1979;1946.
42. Wu, F., Sumiyoshi, T., Yamashita, Y., Shindo, T., Sawamura, S., 1996. Photochemistry of π-complexes of chlorine atom with methyl- and ethyl-substituted benzenes Chem. Lett. 643.
43. Wu F., Shindo T., Sawamura S., Sumiyoshi T. Quantum yields of intramolecular hydrogen abstraction induced by laser flash photolysis of arene/Cl π-complexes. Bull. Chem. Soc. Jpn. 70:1997;1839.
44. Zanker V., Ehrhardt E. On the photochemical behavior of some xanthenes and xanthones and the photochemical formation of dixathenes, mono-, and dihydroxydixanthens. Bull. Chem. Soc. Jpn. 39:1966;1694.