Photoinduced oligomerization of aqueous pyruvic acid

Journal of Physical Chemistry A

Volumn 110, Issue 10, 2006, Pages 3619-3626

  Guzman M I ^a   Colussi, A J ^a   Hoffmann, M R ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL RADICALS; BIMOLECULAR REACTIONS; OLIGOMERIZATION; PYRUVIC ACID;

CARBOXYLATION; DECOMPOSITION; DISSOCIATION; LIQUID CHROMATOGRAPHY; OLIGOMERS; PHOTOCHEMICAL REACTIONS; POLYMERIZATION; REACTION KINETICS; SOLUTIONS;

ORGANIC ACIDS;

EID: 33645525065     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp056097z     Document Type: Article

References (84)

1. Moran, M. A.; Zepp, R. G. Limnol. Oceanogr. 1997, 42, 1307.
2. Andreae, M. O.; Talbot, R. W.; Li, S. M. J. Geophys. Res. 1987, 92, 6635.
3. Mopper, K.; Zhou, X.; Kieber, R. J.; Sikorski, R. G.; Jones, R. D. Nature 1991, 353, 60.
4. Kawamura, K.; Imai, Y.; Barrie, L. A. Atmos. Environ. 2005, 39, 599.
5. Kawamura, K.; Yasui, O. Atmos. Environ. 2005, 39, 1945.
6. Kawamura, K.; Yokoyama, K.; Fujii, Y.; Watanabe, O. J. Geophys. Res. 2001, 106, 1131.
7. Kanakidou, M.; et al. Atmos. Chem. Phys. 2005, 5, 1053.
8. Miller, W. M.; Zepp, R. G. Geophys. Res. Lett. 1995, 22, 417.
9. Fisseha, R.; Dommen, J.; Sax, M.; Paulsen, D.; Kalberer, M.; Maurer, R.; Hofler, F.; Weingartner, E.; Baltensperger, U. Anal. Chem. 2004, 76, 6535.
10. Calvert, G.; Pitts, J. N. Photochemistry; Wiley: New York, 1966.
11. Klotz, B.; Graedler, F.; Sorensen, S.; Barnes, I.; Becker, K. H. Int. J. Chem. Kinet. 2001, 33, 9.
12. Faust, B. P. K.; Rao, C.; Anastasio, C. Atmos. Environ. 1997, 31, 497.
13. Buschmann, H. J.; Dutkiewicz, E.; Knoche, W. Ber. Bunsen-Ges. 1982, 86, 129.
14. Buschmann, H. J.; Fuldner, H. H.; Knoche, W. Ber. Bunsen-Ges. 1990, 84, 41.
15. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776.
16. Budac, D.; Wan, P. J. Photochem. Photobiol., A 1992, 67, 135.
17. Wan, P.; Budac, D. CRC Handbook of Organic Photochemistry and Photobiology; CRC Press: Boca Raton, FL, 1995.
18. Vesley, G. F.; Leermakers, P. A. J. Phys. Chem. 1964, 68, 2364.
19. O'Neal, J. A.; Kreutz, T. G.; Flynn, G. W. J. Chem. Phys. 1987, 87, 4598.
20. Turro, N. J.; Weiss, D. S.; Haddon, W. F.; McLafferty, F. W. J. Am. Chem. Soc. 1967, 89, 3370.
21. Wesdemiotis, C.; McLafferty, F. W. J. Am. Chem. Soc. 1987, 109, 4760.
22. Corner, H.; Khun, H. J. J. Chem. Soc., Perkin Trans. 2 1999, 2671.
23. Closs, G. L.; Miller, R. J. J. Am. Chem. Soc. 1978, 100, 3483.
24. Ronkainen, P.; Brummer, S.; Soumalainen, H. Acta Chem. Scand. 1970, 24, 3404.
25. Sawaki, Y.; Ogata, Y. J. Am. Chem. Soc. 1981, 103, 6455.
26. Kendall, D. S.; Leermakers, P. A. J. Am. Chem. Soc. 1966, 88, 2766.
27. Davidson, R. S.; Goodwin, D. J. Chem. Soc., Perkin Trans. 2 1982, 1559.
28. Davidson, R. S.; Goodwin, D.; Fornier de Violet, P. Chem. Phys. Lett. 1981, 78, 471.
29. Davidson, R. S.; Goodwin, D.; Pratt, J. E. J. Chem. Soc., Perkin Trans. 2 1983, 1729.
30. Formosinho, S. J. J. Chem. Soc., Faraday Trans. 2 1976, 72, 1313.
31. Eberson, L. Adv. Phys. Org. Chem. 1982, 18, 79.
32. Cai, Z.; Sevilla, M. D. Top. Curr. Chem. 2004, 257, 103.
33. Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337.
34. Knoll, H.; Weidemann, F.; Henning, H. React. Kinet. Catal. Lett. 1987, 36, 411.
35. Kieber, D. J.; Blough, N. V. Free Radical Res. Commun. 1990, 10, 109.
36. Kieber, D. J.; Blough, N. V. Anal. Chem. 1990, 62, 2275.
37. Guzmán, M. I.; Colussi, A. J.; Hoffmann, M. R. J. Phys. Chem. A 2006, 120, 931.
38. Ronkainen, P.; Brummer, S.; Soumalainen, H. Anal. Biochem. 1970, 34, 101.
39. NIST online databases, http://webbook.nist.gov/chemistry.
40. Defoin, A.; Defoin-Straatmann, R.; Hilderbrand, K.; Bittersmann, E.; Kreft, D.; Khun, H. J. J. Photochem. 1986, 33, 237.
41. Wagner, P. J.; Zhang, Y.; Puchalski, A. E. J. Phys. Chem. 1993, 97, 13368.
42. Chiang, Y.; Kresge, A. J.; Pruszynski, P. J. Am. Chem. Soc. 1992, 114, 3103.
43. Bandu, M. L.; Watkins, K. R.; Bretthauer, M. L.; Moore, C. A.; Desaire, H. Anal. Chem. 2004, 76, 1746.
44. Qin, X. Z. J. Mass Spectrom. 2003, 38, 677.
45. Moe, M. K. Rapid Commun. Mass Spectrom. 2005, 19, 859.
46. Fischer, G.; Flatau, S.; Schellenberger, A.; Zschunke, A. J. Org. Chem. 1988, 53, 214.
47. Kimura, H. J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 3595.
48. Kimura, H. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 189.
49. Kimura, H. Polym. Adv. Technol. 2001, 12, 697.
50. Aylward, G. H.; Findlay, T. J. V. SI Chemical Data; Wiley: New York, 1986.
51. Neta, P.; Huie, R. E.; Ross, A. B. J. Phys. Chem. Ref. Data 1990, 19, 413.
52. Font-Sanchis, E.; Aliaga, C.; Bejan, E. V.; Cornejo, R.; Scaiano, J. C. J. Org. Chem. 2003, 68, 3199.
53. Scaiano, J. C.; Martin, A.; Yap, G. P. A.; Ingold, K. U. Org. Lett. 2000, 2, 899.
54. Bejan, E. V.; Font-Sanchis, E.; Scaiano, J. C. Org. Lett. 2001, 3, 4059.
55. El-Agamey, A.; McGarvey, D. J. J. Am. Chem. Soc. 2003, 125, 3330.
56. Saxena, P.; Hildemann, L. M. Environ. Sci. Technol. 1997, 31, 3318.
57. Jang, M.; Czoschke, N. M.; Northcross, A. L. ChemPhysChem 2004, 5, 1646.
58. Davidson, R. S.; Goodwin, D.; Turnock, G. Tetrahedron Lett. 1980, 27, 4943.
59. Liu, X.; Gross, M. L.; Wenthold, P. G. J. Phys. Chem. A 2005, 109, 2183.
60. Griesbeck, A. G.; Kramer, W.; Oelgemoller, M. Synlett 1999, 1169.
61. Abel, B.; Assmann, J.; Buback, M.; Grimm, C.; Kling, M.; Schmatz, S.; Schroeder, J.; Witte, T. J. Phys. Chem. A 2003, 107, 9499.
62. Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Org. Chem. 1997, 62, 2210.
63. Step, E. N.; Buchachenko, A. L.; Turro, N. J. J. Am. Chem. Soc. 1994, 116, 5462.
64. Step, E. N.; Buchachenko, A. L.; Turro, N. J. J. Org. Chem. 1992, 57, 7018.
65. Nakao, L. S.; Kadiiska, M. B.; Mason, R. P.; Grijalba, M. T.; Augusta, O. Free Radical Biol. Med. 2000, 29, 721.
66. Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200.
67. Schuchmann, M. N.; von Sonntag, C. J. Am. Chem. Soc. 1988, 110, 5698.
68. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469.
69. Negron-Mendoza, A.; Castillo, S.; Torres, J. L.; Albarran, G. Radiat. Phys. Chem. 1988, 31, 825.
70. Martin, C.; Huser, H.; Servat, K.; Kokoh, K. B. Electrochim. Acta 2005, 50, 2431.
71. Guthrie, J. P. Bioorg. Chem. 2002, 30, 32.
72. Huang, C. L.; Wu, C. C.; Lien, M. H. J. Phys. Chem. A 1997, 101, 7867.
73. Sayre, L. M.; Jensen, F. R. J. Org. Chem. 1978, 43, 4700.
74. Adams, G. E.; Willson, R. L. J. Chem. Soc., Faraday Trans. 1 1973, 69, 719.
75. von Sonntag, C.; Schuchmann, M. N. Angew. Chem., Int. Ed. 1991, 30, 1229.
76. Mezyk, S. P.; Cooper, W. J.; Madden, K. P.; Bartels, D. M. Environ. Sci. Technol. 2004, 38, 3161.
77. Denisova, T. G.; Denisov, E. T. Petroleum Chem. 2005, 45, 26.
78. Samuni, A.; Behar, D.; Fessenden, R. W. J. Phys. Chem. 1973, 77, 777.
79. Colussi, A. J. Chemical Kinetics of Small Organic Radicals; CRC Press: Boca Raton, FL, 1988; Vol. 1.
80. Jockusch, S.; Turro, N. J. J. Am. Chem. Soc. 1999, 121, 3921.
81. Faraji, H.; Lindsay, R. C. J. Agric. Food Chem. 2005, 53, 736.
82. Yadav, P.; Rao, B. S. M.; Batchelor, S. N.; O'Neill, P. J. Phys. Chem. A 2005, 109, 2039.
83. Gillbe, C. E.; Sage, F. J.; Gutteridge, J. M. C. Free Radical Res. 1996, 24, 1.
84. Morelli, R.; Russo-Volpe, S.; Bruno, N.; Lo Scalzo, R. J. Agric. Food Chem. 2003, 51, 7418.