Effect of substituents on different channels of .OH radical reaction with substituted organic sulfides

Radiation Physics and Chemistry

Volumn 74, Issue 3-4, 2005, Pages 220-226

  Mohan, Hari ^a   Mittal, Jai P ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

Aqueous solution; Pulse radiolysis; Substituted organic sulfides

Indexed keywords

ABSORPTION; BENZENE; CARBOXYLIC ACIDS; DIMERS; RADIATION CHEMISTRY; SOLUTIONS; SULFUR COMPOUNDS;

NEUTRAL AQUEOUS SOLUTION; ORGANIC SULFIDES; PROPIONIC ACID; TRANSIENT ABSORPTION;

RADIOLYSIS;

3,3' THIODIPROPIONIC ACID; 3,3' THIODIPROPIONITRILE; ACETIC ACID; ACID; BENZENE; CATION; DIMER; DIMETHYL 2,2' THIODIETHANOIC ACID; GLYCOLIC ACID DERIVATIVE; HYDROXYL RADICAL; METHYL PROPYL SULFIDE; MONOMER; NITRILE; ORGANOSULFUR DERIVATIVE; OXYGEN; PROPIONIC ACID DERIVATIVE; RADICAL; SULFIDE; SULFUR; THIODIACETIC ACID; UNCLASSIFIED DRUG;

ABSORPTION; ACIDITY; AQUEOUS SOLUTION; ARTICLE; CONCENTRATION (PARAMETERS); ELECTRON; OXIDATION; PULSE RADIOLYSIS; RADICAL REACTION; REACTION ANALYSIS;

EID: 23944443254     PISSN: 0969806X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.radphyschem.2005.04.016     Document Type: Article

References (41)

1. E. Anklam, H. Mohan, and K.-D. Asmus 2σ-1σ* three electron bonded radical cations from alkylthio(halogeno)alkanes J. Chem. Soc. Perkin Trans. 2 1988 1297 1302
2. K.-D. Asmus Stabilization of oxidized sulfur centers in organic sulfides. Radical cations and odd-electron sulfur-sulfur bonds Acc. Chem. Res. 12 1979 435 442
3. K.-D. Asmus, D. Bahnemann, Ch.H. Fisher, and V. Veltwisch Structure and stability of radical cations from cyclic and open chain dithia compounds in aqueous solution J. Am. Chem. Soc. 101 1979 5322 5327
4. K.-D. Asmus, M. Göbl, K.-O. Hiller, S. Mahling, and J. Mönig S∴N and S∴O three-electron bonded radical cations in aqueous solutions J. Chem. Soc. Perkin Trans. 2 1985 641 646
5. K. Bobrowski, and J. Holcman Formation and stability of intramolecular three-electron S∴N, S∴S and S∴O bonds in one-electron-oxidized simple methionine peptides: pulse radiolysis study J. Phys. Chem. 93 1989 6381 6387
6. K. Bobrowski, and C. Schöneich Hydroxyl radical adduct at sulfur in substituted organic sulfides stabilized by internal hydrogen bond J. Chem. Soc. Chem. Commun. 1993 795 797
7. K. Bobrowski, B. Marciniak, and G.L. Hug 4-carboxybenzophenone-sensitized photooxidation of sulfur-containing amino acids: nanosecond laser flash photolysis and pulse radiolysis studies J. Am. Chem. Soc. 114 1992 10279 10288
8. .OH radical induced decarboxylation of 2-(alkylthio)ethanoic acid derivatives J. Phys. Chem. 97 1993 13677 13684
9. K. Bobrowski, G.L. Hug, B. Marcinik, B. Miller, and C. Schöneich Mechanism of one-electron oxidation of β-, γ-, and δ-hydroxyalkyl sulfides: catalysis through intramolecular proton transfer and sulfur-oxygen bond formation J. Am. Chem. Soc. 119 1997 8000 8011
10. 2S∴ X radicals in aqueous solution J. Chem. Soc. Perkin Trans. 2 1980 758 762
11. M. Bonifacic, H. Möckel, D. Bahnemann, and K.-D. Asmus Formation of positive ions and other primary species in the oxidation of sulfides by hydroxyl radicals J. Chem. Soc. Perkin Trans. 2 1975 675 685
12. C. Chatgilialoglu, and K.-D. Asmus Sulfur Centered Reactive Intermediates in Chemistry and Biology, NATO ASI Series A, Life Sciences 1990 Plenum Press New York
13. C. Chatgilialoglu, M.P. Bertrand, and C. Ferreri Sulfur-centered radicals in organic synthesis Z.B. Alfassi S-Centered Radicals 1999 Wiley UK 311 354
14. T. Clark Odd-electron σ bonds J. Am. Chem. Soc. 110 1988 1672 1678
15. L. Engman, J. Lind, and G. Merenyi Redox properties of diaryl chalcogenides J. Phys. Chem. 98 1994 3174 3182
16. .OH radical reaction with substituted dialkyl sulfides J. Chem. Soc. Perkin Trans. 2 1999 1425 1432
17. V.B. Gawandi, H. Mohan, and J.P. Mittal Evidence for the role of electron-withdrawing power of functional groups and [H+] for electron transfer reaction in substituted alkyl sulfides J. Phys. Chem. A 104 2000 11877 11884
18. + in the one-electron oxidation of sulfides J. Chem. Soc. Perkin Trans. 2 1973 1748 1753
19. M. Göbl, and K.-D. Asmus The reaction of α-(alkylthio)alkyl radicals with tetranitromethane: pulse radiolysis evidence for an intermediate radical adduct J. Chem. Soc. Perkin Trans. 2 1984 691 697
20. M. Göbl, M. Bonafacic, and K.-D. Asmus Substituents effects on the stability of three electron bonded radicals and radical ions from organic sulfur compounds J. Am. Chem. Soc. 106 1984 5984 5988
21. R.S. Glass Sulfur radical cations Topics in Curr. Chem. 205 1999 1 87 Springler, Berlin
22. S.N. Guha, P.N. Moorthy, K. Kishore, and K.N. Rao One-electron reduction of thionine studied by pulse radiolysis Proc. Ind. Acad. Sci. (Chem. Sci.) 99 1987 261 271
23. H. Hungerbühler, S.N. Guha, and K.-D. Asmus Radical cation with a sulfur-phosphorus 2σ-1σ* three-electron bond in solution J. Chem. Soc. Chem. Commun. 1991 999 1001
24. M. Ioele, S. Steenken, and E. Baciocchi Generation and reactivity of aromatic thioether radical cations in aqueous solution as studied by pulse radiolysis J. Phys. Chem. A 101 1997 2979 2987
25. S.A. Korzeniowska, G.L. Hug, I. Carmichael, and K. Bobrowski Spectral, kinetics and theoretical studies of radical cations derived from thioanisole and its carboxylic derivative J. Phys. Chem. A 106 2002 9251 9260
26. F.D. Lewis M.A. Fox M. Chanon Photoinduced Electron Transfer, Part C 1988 Elsevier Amsterdam 1 69
27. D.K. Maity Structure bonding and spectra of cyclic dithia radical cations: a theoretical study J. Am. Chem. Soc. 124 2002 8321 8328
28. D.K. Maity, H. Mohan, and J.P. Mittal Characterization of transients formed in aqueous solutions of substituted alkyl sulfides: a pulse radiolysis study J. Chem. Soc. Faraday Trans. 90 1994 703 709
29. B. Marciniak, G.L. Hug, J. Rozwadowski, and K. Bobrowski Excited triplet state of N-(9-methylpurin-6-yl)pyridinium cations as an efficient photosensitizer in the oxidation of sulfur containing amino acids. Laser flash and steady state photolysis studies J. Am. Chem. Soc. 117 1995 127 134
30. B. Marciniak, E. Andrzejewska, and G.L. Hug Photoreduction of benzophenone by 2,4,6- trimethyl-1,3,5-trithiane in solution. Laser flash photolysis study J. Photochem. Photobiol. 112 1998 21 28
31. M.L. McKee Comparison of gas-phase and solution-phase reactions of dimethyl sulfides and 2-(methylthio)ethanol with hydroxyl radical J. Phys. Chem. A 107 2003 6819 6827
32. H. Mohan Intra- and inter-molecular electron transfer reactions in 3,3′-thiodipropionuc acid J. Chem. Soc. Perkin Trans, 2 1990 1821 1824
33. H. Mohan, and J.P. Mittal Pulse radiolysis investigations on electron-transfer reactions in aqueous solutions of substituted alkyl sulfides J. Chem. Soc. Perkin Trans. 2 1992 207 212
34. H. Mohan, and J.P. Mittal Different channels of hydroxyl radical reaction with aryl sulfides: effect of the substitution J. Phys. Chem. A 106 2002 6574 6580
35. K. Mizuno, and Y. Otsuji Addition and cycloaddition reactions via photoinduced electron transfer Top. Curr. Chem. 169 1994 302 346
36. J. Mönig, M. Göbl, and K.-D. Asmus Free radical one-electron versus hydroxyl radical induced oxidation: reaction of trichloromethylperoxyl radicals with simple and substituted aliphatic sulfides in aqueous solution J. Chem. Soc. Perkin Trans. 2 1985 647 651
37. C. Schöneich, and K. Bobrowski Intramolecular hydrogen transfer as the key step in the dissociation of hydroxyl radical adduct of (alkylthio)ethanol derivatives J. Am. Chem. Soc. 115 1993 6538 6547
38. C.von. Sonntag The Chemical Basis of Radiation Biology 1987 Taylor and Francis New York
39. R.W. Taft Concerning the electron-withdrawing power and the electronegativity of groups J. Chem. Phys. 26 1957 93 96
40. S.P. Urbanski, and P.H. Wine Chemistry of gas phase organic sulfur-centered radicals Z.B. Alfassi S-Centered Radicals 1999 Wiley UK 97 140
41. N. Varmenot, J. Berges, Z. Abedinzadeh, A. Scemama, G. Strzelczak, and K. Bobrowski Spectral, kinetic and theoretical studies of sulfur-centered reactive intermediates derived from th ioethers containing an acetyl group J. Phys. Chem. A 108 2004 6331 6346