Spectral, kinetic, and theoretical studies of sulfur-centered reactive intermediates derived from thioethers containing an acetyl group

Journal of Physical Chemistry A

Volumn 108, Issue 30, 2004, Pages 6331-6346

  Varmenot, Nicolas ^a   Bergès, Jacqueline ^a,b   Abedinzadeh, Zohreh ^a   Scemama, Anthony ^b   Strzelczak, Grazyna ^c   Bobrowski, Krzysztof ^c  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b LABORATOIRE DE CHIMIE THÉORIQUE   (France)

^c INSTITUTE OF NUCLEAR CHEMISTRY AND TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; CATALYSIS; COMPUTATIONAL METHODS; COMPUTER SIMULATION; ERROR CORRECTION; ETHERS; GAS CHROMATOGRAPHY; PARAMAGNETIC RESONANCE; PERTURBATION TECHNIQUES; PH EFFECTS; PROBABILITY DENSITY FUNCTION; RADIOLYSIS; REACTION KINETICS; SOLUTIONS; SPECTROPHOTOMETRY;

CONDUCTOR POLARIZED CONTINUUM MODEL (CPCM) METHOD; DEPROTONATION; REACTIVE INTERMEDIATES; ZERO-POINT ENERGY (ZPE) CORRECTIONS;

SULFUR COMPOUNDS;

EID: 4043049694     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp031159b     Document Type: Article

References (69)

1. Glass, R. S. Neighbouring Group Participation: General Principles and Application to Sulfur-Centered Reactive Species. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds; Plenum Press: New York, 1990; Vol. 97, p 213.
2. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Press: New York, 1976; Vol. 1.
3. Asmus, K.-D. Heteroatom-Centered Free Radicals: Some Selected Contributions by Radiation Chemistry. In Radiation Chemistry; Present Status and Future Prospects; Jonah, C., Rao, B. S. M., Eds.; Elsevier: Amsterdam, 2001.
4. Asmus, K.-D. Nukleonika 2000, 45, 3-10.
5. Asmus, K.-D.; Bonifačić, M. Sulfur-Centered Reactive Intermediates as Studied by Radiation Chemical and Complementary Techniques. In S-CenteredRadicals; Alfassi, Z. B., Ed.; John Wiley & Sons: Chichester, U.K., 1999; pp 141-191.
6. Glass, R. S.; Hojjatie, M.; Petsom, A.; Wilson, G. S.; Göbl, M.; Mahling, S.; Asmus, K.-D. Phosphorus Sulfur Relat. Elem. 1985, 23, 143-168.
7. Schöneich, C.; Pogocki, D.; Wisniowski, P.; Hug, G. L.; Bobrowski, K. J. Am. Chem. Soc. 2000, 122, 10224-10225.
8. Gawandi, V. B.; Mohan, H.; Mittal, J. P. J. Phys. Chem. A 2000, 104, 11877-11884.
9. Bobrowski, K.; Hug, G. L.; Marciniak, B.; Schöneich, C.; Wiśniowski, P. Res. Chem. Interned. 1999, 25, 285-297.
10. Gawandi, V. B.; Mohan, H.; Mittal, J. P. Phys. Chem. Chem. Phys. 1999, 1, 1919-1926.
11. Gawandi, V. B.; Mohan, H.; Mittal, J. P. J. Chem. Soc., Perkin Trans. 2 1999, 1425-1432.
12. Bobrowski, K.; Pogocki, D.; Schöneich, C. J. Phys. Chem. A 1998, 102, 10512-10521.
13. Schöneich, C.; Zhao, F.; Madden, K. P.; Bobrowski, K. J. Am. Chem. Soc. 1994, 116, 4641-4652.
14. Schöneich, C.; Bobrowski, K. J. Am. Chem. Soc. 1993, 115, 6538-6547.
15. Bobrowski, K.; Pogocki, D.; Schöneich, C. J. Phys. Chem. 1993, 97, 13677-13684.
16. Bobrowski, K.; Schöneich, C. J. Chem. Soc., Chem. Commun. 1993, 795-797.
17. Mohan, H.; Mittal, J. P. J. Chem. Soc., Perkin Trans. 2 1992, 207-212.
18. Bobrowski, K.; Schöneich, C.; Holcman, J.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1991, 975-980.
19. Bobrowski, K.; Schöneich, C.; Holcman, J.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1991, 353-362.
20. Steffen, L. K.; Glass, R. S.; Sabahi, M.; Wilson, G. S.; Schöneich, C.; Mahling, S.; Asmus, K.-D. J. Am. Chem. Soc. 1991, 113, 2141-2145.
21. Mohan, H.; Mittal, J. P. Radiat. Phys. Chem. 1991, 38, 45-50.
22. Bobrowski, K.; Wierzchowski, K. L.; Holcman, J.; Ciurak, M. Int. J. Radiat. Biol. 1990, 57, 919-932.
23. Mohan, H.; Moorthy, P. N. J. Chem. Soc., Perkin Trans. 2 1990, 413-416.
24. Mohan, H. J. Chem. Soc., Perkin Trans. 2 1990, 1821-1824.
25. Asmus, K.-D. Sulfur-Centered Three-Electron Bonded Radical Species. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990; Vol. 197, pp 155-172.
26. Bobrowski, K.; Holcman, J. J. Phys. Chem. 1989, 93, 6381-6387.
27. Asmus, K.-D.; Göbl, M.; Hiller, K.-O.; Mahling, S.; Mönig, J. J. Chem. Soc., Perkin Trans. 2 1985, 641-646.
28. Killer, K.-O.; Masloch, B.; Gobi, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743.
29. Schöneich, C. Exp. Gerontol. 1999, 34, 19-34.
30. Stadtman, E. R. Free Radical Mediated Oxidation of Proteins; Ozben, T., Ed.; Plenum Press: New York, 1998; Vol. 296, pp 51-64.
31. Levine, R. L.; Berlett, B. S.; Moskovitz, J.; Mosoni, L.; Stadtman, E. L. Mech. Aging Dev. 1999, 107, 323-332.
32. Levine, R. L.; Mosoni, L.; Berlett, B. S.; Stadtman, E. R. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 15036-15040.
33. Schöneich, C.; Zhao, F.; Yang, J.; Miller, B. Mechanisms of Methionine Oxidation in Peptides; Shahrokh, Z., Sluzky, V., Cleland, J. L., Shire, S. J., Randolph, T. W., Eds.; American Chemical Society: Washington, DC, 1997; Vol. 675, pp 79-89.
34. Varmenot, N.; Remita, S.; Abedinzadeh, Z.; Wisniowski, P.; Strzelczak, G.; Bobrowski, K. J. Phys. Chem. A 2001, 105, 6867-6875.
35. Ogino, K.; Fujihara, H. Biochemical Reactions Involving Thioesters; Oae, S., Okuyama, T., Eds.; CRC Press: Boca Raton, FL, 1998; pp 71-136.
36. Ellman, G. L. A. Arch. Biochem. Biophys. 1959, 82, 70-77.
37. Karolczak, S.; Hodyr, K.; Polowinski, M. Radiat. Phys. Chem. 1992, 39, 1.
38. Karolczak, S.; Hodyr, K.; Lubis, R.; Kroh, J. J. Radioanal. Nucl. Chem. 1986, 101, 177.
39. Schuler, R. H.; Patterson, L. K.; Janata, E. J. Phys. Chem. 1980, 84, 2088.
40. Kobayashi, K.; Tanaka, M.; Kawai, S. J. Chromatogr. 1980, 187, 413-417.
41. Antonini, E.; Brunori, M. The Derivatives of Ferrous Hemoglobin and Myoglobin; North-Holland: Amsterdam, 1971; Vol. 21.
42. Rauk, A.; Armstrong, D. A.; Berges, J. Can. J. Chem. 2001, 79, 405-417.
43. Vreck, I. V.; Siehl, H.-U. J. Phys. Chem. A 2002, 106, 1604-1611.
44. Carmichael, I. Nukleonika 2000, 45, 11-17.
45. Braida, B.; Hiberty, P. C.; Savin, A. J. J. Phys. Chem. A 1998, 102, 7872-7877.
46. Li, X.; Cai, Z.; Seville, M. D. J. Phys. Chem. A 2002, 106, 1596-1603.
47. McKee, M. L. J. Phys. Chem. 1993, 97, 10971-10976.
48. Cossi, M.; Barone, V.; Menucci, B.; Tomasi, J. Chem. Phys. Lett. 1998, 280, 253-260.
49. Cossi, M.; Adamo, C.; Barone, V. Chem. Phys. Lett. 1998, 297, 1-7.
50. Jolibois, F.; Cadet, J.; Grand, A.; Subra, R.; Rega, N.; Barone, V. J. Am. Chem. Soc. 1998, 120, 6706-6712.
51. Schuurmann, G.; Cossi, M.; Barone, V.; Tomasi, J. J. Phys. Chem. A 1998, 102, 6706-6712.
52. Lhiaubet, V.; Gutierrez, F.; Penaud-Berruyer, F.; Amouyal, E.; Daudey, J.-P.; Poteau, R.; Chouini-Lalanne, N.; Paillous, N. New J. Chem. 2000, 24, 403-410.
53. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
54. Schuler, R. H.; Hartzell, A. L.; Behar, B. J. Phys. Chem. 1981, 55, 192-199.
55. von Sonntag, C.; Schuchmann, H.-P. Peroxyl Radicals in Aqueous Solutions; Alfassi, Z. B., Ed.; John Wiley & Sons: Chichester, U.K., 1997; pp 173-234.
56. Zhang, X.; Zgang, N.; Schuchmann, H.-P.; von Sonntag, C. J. Phys. Chem. 1994, 98, 6541-6547.
57. Tamba, M.; Simone, G.; Quintilani, M. Int. J. Radiat. Biol. 1986, 50, 595-600.
58. Jayson, G. G.; Stirling, D. A.; Swallow, A. J. Int. J. Radiat. Biol. 1971, 19, 143-156.
59. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513-886.
60. Varmenot, N.; Berges, J.; Scemama, A.; Abedinzadeh, Z.; Bobrowski, K., to be submitted for publication.
61. Braida, B.; Hazebroucq, S.; Hiberty, P. C. J. Am. Chem. Soc. 2002, 124, 2371-2378.
62. Bonifačić, M.; Möckel, H.; Bahnemann, D.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1975, 675-685.
63. Fourré, I.; Berges̀, J. J. Phys. Chem. A 2004, 108, 898-906.
64. McKee, M. L. J. Phys. Chem. A 2003, 107, 6819-6827.
65. Wisniowski, P.; Filipiak, P.; Bobrowski, K.; Hug, G. L., to be submitted for publication.
66. Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry; Prentice Hall: Upper Saddle River, NJ, 1992.
67. Avilla, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 446-470.
68. Bordwell, F. G.; Zhang, X.-M.; Alnajjarr, M. S. J. Am. Chem. Soc. 1992, 114, 7623-7629.
69. Sustmann, R.; Korth, H.-G. Adv. Phys. Org. Chem. 1990, 26, 131-178.