Linear free energy relationship analysis of solvent effects on singlet oxygen reactions

Current Organic Chemistry

Volumn 7, Issue 9, 2003, Pages 799-819

  Lemp, Else ^a   Zanocco, Antonio L ^a   Lissi, Eduardo A ^b  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ACTIVATION ENERGY; CHARGE TRANSFER; FREE ENERGY; OXYGEN; RATE CONSTANTS; REACTION INTERMEDIATES; SOLVATION;

DESCRIPTORS; FUROSEMIDES; LINEAR FREE ENERGY RELATIONSHIPS; LINEAR SOLVATION ENERGY RELATIONSHIPS; QUANTITATIVE EVALUATION; REACTION MECHANISM; RELATIONSHIP ANALYSIS; RELATIVE CONTRIBUTION; SINGLET OXYGEN REACTION; SOLVENT EFFECTS;

SOLVENTS;

1,4 DIAZABICYCLO[2.2.2]OCTANE; ALKADIENE; ALKENE DERIVATIVE; AMINE; AMINO ACID DERIVATIVE; AROMATIC COMPOUND; BOLDINE; FURAN DERIVATIVE; FUROSEMIDE; LIDOCAINE; PIROXICAM; POLYFUNCTIONAL GROUP; RESERPINE; SINGLET OXYGEN; SOLVENT; TENOXICAM; TETRAHYDROFURAN; TRIETHYLAMINE; VINCAMINE;

ACIDITY; CHEMICAL PARAMETERS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; CORRELATION COEFFICIENT; CYCLOADDITION; DRUG MECHANISM; DRUG METABOLISM; DRUG STRUCTURE; EDEMA; ELECTRICITY; HUMAN; LINEAR ENERGY TRANSFER; PH MEASUREMENT; PHOTOSENSITIVITY DISORDER; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; REVIEW; SIDE EFFECT; SOLVATION; SOLVENT EFFECT;

EID: 0038363922     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033486657     Document Type: Review

References (95)

1. Briviba, K.; Klotz, L.-O.; Sies, H. Biol. Chem. 1997, 378, 1259.
2. Hultén, L.M.; Holmström, M.; Soussi, B. Free Radical Biol. Med. 1999, 27, 1203.
3. Lissi, E.A.; Encinas, M.V.; Lemp, E.; Rubio, M.A. Chem. Rev. 1993, 93, 699.
4. Lissi, E.A.; Rubio, M.A. Pure Appl. Chem. 1990, 62, 1505.
5. Lissi, E.A.; Lemp, E.; Zanocco, A.L. In Understanding and Manipulating Excited-State Processes; Ramamurthy, V.; Schanze, K.S., Ed.; Marcel Dekker, New York, 2001; Vol. 4, pp. 287-316.
6. Wilkinson, F.; Brummer, J.G. J. Phys. Chem. Ref. Data, 1981, 10, 809;
7. Wilkinson, F.; Helman, W.P.; Ross, A.B. http://allen.rad.nd.edu/compilations/SingOx.
8. Palumbo, M.C.; García, N.A.; Arguello, G.A. J. Photochem. Photobiol. B: Biol. 1990, 7, 33.
9. Mandard-Cazin, B.; Aubry, J.-.M.; Rigaudy, J. J. Chem. Soc., Chem. Commun. 1986, 952.
10. Gollnick, K.; Griesbeck, A. Tetrahedron Lett. 1984, 25, 725.
11. Mártire, D.O.; Braslavsky, S.E.; García, N.A. J. Photochem. Photobiol. A: Chem. 1991, 61, 113.
12. Aubry, J.-.M.; Mandard-Cazin, B.; Rougee, M.; Bensasson, R.V.; J. Am. Chem. Soc. 1995, 117, 9159.
13. Taft, R.W.; Abboud, J.L.M.; Abraham, M.H. J. Solution Chem. 1985, 14, 153-186.
14. Reichardt, C. Solvents and Solvents Effects in Organic Chemistry, 2nd ed. VCH, Weinheim, 1988.
15. Kamlet, M.J.; Abboud, J.L.M.; Abraham, M.H.; Taft, R.W. J. Org. Chem. 1983, 48, 2877.
16. Kamlet, M.J.; Abboud, J.L.M.; Taft, R.W. Prog. Phys. Org. Chem. 1981, 13, 485.
17. Kamlet, M.J.; Taft, R.W. J. Am. Chem. Soc. 1976, 98, 377.
18. Taft, R.W.; Kamlet, M.J. J. Am. Chem. Soc. 1976, 98, 2886.
19. Taft, R.W.; Kamlet, M.J. J. Am. Chem. Soc. 1977, 99, 6027.
20. Reichardt, C.; Chem. Rev. 1994, 94, 2319.
21. Taft, R.W.; Kamlet, M.J. J. Am. Chem. Soc., Perkin Trans. II, 1979, 1723.
22. Maria, P.C.; Franceschi, J.F.; Fargin, E. J. Am. Chem. Soc. 1987, 109, 483.
23. Kamlet, M.J.; Carr, P.W.; Taft, R.W.; Abraham, M.H. J. Am. Chem. Soc. 1981, 103, 6062.
24. Taft, R.W.; Abboud, J.L.M.; Kamlet, M.J. J. Am. Chem. Soc. 1981, 103, 1080.
25. Abboud, J.L.M.; Kamlet, M.J.; Taft, R.W. J. Am. Chem. Soc. 1977, 99, 8325.
26. Kamlet, M.J.; Taft, R.W. Acta Chem. Scand. B, 1985, 39, 611.
27. Cramer, C.J.; Famini, G.R.; Lowrey, A.H. Acc. Chem Res. 1993, 26, 599.
28. Famini, G.R.; Wilson, L.Y. J. Chem. Soc., Perkin Trans 2, 1994, 1641.
29. Donovan, W.H.; Famini, G.R. J. Chem. Soc., Perkin Trans 2, 1995, 83.
30. Lowrey, A.H.; Famini, G.R.; Wilson, L.Y. J. Chem. Soc., Perkin Trans 2, 1997, 1381.
31. Cronce, D.T.; Famini, G.R.; De Soto, J.A.; Wilson, L.Y. J. Chem. Soc., Perkin Trans 2, 1998, 1293.
32. Hopfinger, A.J.; J. Am. Chem. Soc., 1980, 102, 7126.
33. Kurtz, H.A.; Stewart, J.J.P.; Dieter, K.M. J. Compt. Chem., 1990, 11, 82.
34. Dewar, M.J.S.; Thiel, W. J. Am. Chem. Soc., 1977, 99, 4899.
35. Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc., 1985, 107, 3902.
36. Lowery, A.H.; Famini, G.R. Struct. Chem., 1995, 6, 357.
37. Famini, G.R.; Wilson, L.Y. Org. React., 1995, XXIX, 117.
38. Headley, A.H.; Starnes, S.D.; Wilson, L.Y.; Famini, G.R. J. Org. Chem., 1994, 59, 8040.
39. Famini, G.R.; Wilson, L.Y. J. Phys. Org. Chem. 1999, 12, 645.
40. Famini, G.R.; Benyamin, D.; Kim, C.; Veerawat, R.; Wilson, L.Y. Collect. Czech. Chem. Commun. 1999, 64, 1727.
41. Marcus, Y. Chem. Soc. Rev. 1993, 22, 409.
42. Barton, A.F.M. Chem. Rev. 1975, 75, 731.
43. Abraham, M.H.; Doherty, R.M.; Kamlet, M.J.; Harris, J.M.; Taft, R.W. J. Chem. Soc. Perkin Trans. II. 1987, 913.
44. Cronce, D.T.; Famini, G.R.; De Soto, J.A.; Wilson, L.Y. http://www.rsc.org/suppdata/perkin2/1998/1293
45. Bellus, D. Singlet Oxygen. Reactions with Organic Compounds and Polymers; Ranby, B., Rabek J. F. Ed. Wiley, New York, 1978.
46. Young, R.H.; Martin, R.L.; Feriozi, D.; Brewer, D.; Kaiser, R. Photochem. Photobiol, 1973, 17, 233.
47. B. M. Monroe, J. Phys. Chem. 1977, 81, 1861.
48. Manring, L.E.; Foote, C.S. J. Phys. Chem. 1982, 86, 1257.
49. Gorman, A.A.; Hamblett, I.; Lambert, C.; Spencer, B.; Standem, M.C. J. Am. Chem. Soc. 1988, 110, 8053.
50. Ogryzlo, E.A.; Tang, C.W. J. Am. Chem. Soc. 1970, 92, 5034.
51. Cazin, B.; Aubry, J.-M.; Rigaudy, J. J. Chem. Soc. Chem. Commun. 1986, 952.
52. Encinas, M.V.; Lemp, E.; Lissi, E.A. J. Chem. Soc. Perkin Trans. 2 1987, 1125.
53. Clennan, E.L.; Noe, L.J.; Wen, T.; Szneler, E. J. Org. Chem. 1989, 54, 3581.
54. Zanocco, A.L.; Günther, G.; Lemp, E.; De La Fuente, J.R.; Pizarro, N. J. Photochem. Photobiol., 2001, 140, 109.
55. Ogilby, P.R.; Dillon, M.P.; Kristiansen, M.; Clough, R.L. Macromolecules, 1992, 25, 3399.
56. Iu, K.-K.; Thomas, J.K. J. Am. Chem. Soc., 1990, 112, 3319.
57. Gorman, A.A.; Hamblett, I.; Smith, K.; Standen, M.C. Tetrahedron Lett., 1984, 25, 581.
58. Seikel, K.; Brauer, H.-D. Ber. Bunsenges. Phys. Chem., 1991, 95, 900.
59. Iu, K.-K.; Thomas, J.K. Photochem. Photobiol., 1993, 71, 55.
60. Salokhiddinov, K.I.; Dzhagarov, B.M.; Byteva, I.M.; Gurinovich, G.P. Chem. Phys. Lett., 1980, 76, 85.
61. Darmanyan, A.P.; Jenkins, W.S. J. Phys. Chem. A, 1998, 102, 7420.
62. Pfeiffer, C.J.; Keith, J.C.; Cho, C.H.; De Rolf, C.; Pfeiffer, D.C.; Misra, H.P. Acta Phys. Hung., 1989, 73, 129.
63. Nasser, F.N.; Walls, J.T.; Edwarrds, W.D.; Harrison, C.E. Am. J. Cardiol., 1980, 46, 967.
64. Boudolulars, H.; Karayannacos, P.E.; Lewis, R.P.; Kakos, G.S.; Kilman, J.W.; Vasco, J.S. J. Sur. Res., 1978, 24, 469.
65. Das, K.C.; Misra, H.P. Mol. Cell. Biochem. 1992, 115, 179-185
66. Stevens, B.; Perez, S.R. Mol. Photochem., 1974, 6, 1.
67. Monroe, B.M. J. Phys. Chem. 1978, 82, 15.
68. Rubio, M.A.; Araya, L.; Abuin, E.B.; Lissi, E.A. An. Soc. Quím. Argent. 1985, 73, 301.
69. Clennan, E.L.; Mehrsheikh-Mohammadi, M.E. J. Am. Chem. Soc. 1983, 105, 5932.
70. Gollnick, K.; Griesberg, A. Tetrahedron, 1986, 41, 207.
71. Okamoto, M.; Tanaka, F.; Teranishi, H. J. Phys. Chem. 1990, 94, 669.
72. Zanocco, A.L.; Günther, G.; Lemp, E.; De La Fuente, J.R.; Pizarro, N. Photochem. Photobiol, 1998, 68, 487.
73. Speisky, H.; Cassels, B.K.; Lissi, E.A.; Videla, L.A. Biochem. Pharmacol., 1991, 41, 1575.
74. Valenzuela, A; Nieto, S.; Cassels, B.K.; Speisky, H. J. Am. Oil Chem. Soc., 1991, 68, 935.
75. Cederbaum, A.; Kukielka, E.; Speisky, H. Biochem. Pharmacol., 1992, 44, 1765.
76. Zanocco, A.L.; Lemp, E.; Günther, G. J. Chem. Soc. Perkin Trans II, 1997, 1299.
77. Thomas, M.J.; Foote, C.S. Photochem. Photobiol., 1978, 25, 683.
78. Magnus, I. A. In Dermatological Photobiology. Blackwells, London. 1976, pp 213-216.
79. Moore, D.E. J. Pharm. Sci. 1977, 66, 1282.
80. Moore, D. E. and Burt, C. D. Photochem. Photobiol. 1981, 34, 431-439.
81. Lemp, E.; Zanocco, A.L.; Günther, G. J. Photochem. Photobiol B: Biol., In Press.
82. Fjellner, B. Acta Derm. Venerol., 1983, 63, 557-558.
83. Serrano, G.; Bonillo, J.; Aliaga, A.; Cuadra, J.; Pujol, C.; Cervero, P.; Miranda, M. A. J. Am. Acad. Dermatol., 1990, 23, 479.
84. Miranda, M.A.; Vargas, F.; Serrano, G. J. Photochem. Photobiol. B: Biol., 1991, 8, 199.
85. Nascimento, A.L.; Escobar, J.A.; Cilento, G. Photochem. Photobiol., 1993, 57, 362.
86. Takács-Novák, K.; Kökösi, J.; Dodanyi, B.; Noszál, B.; Tsai, R.S.; Lisa, G.; Carrupt, P.A.; Testa, B. Helv. Chim. Acta 1995, 78, 553.
87. Gekle, J.M.; Rescek, D.M.; Whipple, E.B. Magn. Reson. Chem., 1989, 27, 150.
88. Marcus, Y. J. Chem. Soc. Perkin Trans 2, 1994, 1751.
89. Lemp, E.; Pizarro, N.; Encinas, M.V.; Zanocco, A.L. Phys. Chem. Chem. Phys. 2001, 3, 5222.
90. Mandal, K.; Kono, M.; Bose, S.K.; Thomson, J.; Chakrabarti, B. Photochem. Photobiol. 1988, 47, 583.
91. Balasubramanian, D.; Du, X.; Zigler, J.S. Photochem. Photobiol. 1990, 52, 761.
92. Palumbo, M.C.; Garcia, N.A.; Arguello, G.A. J. Photochem. Photobiol. B: Biol., 1990, 7, 33.
93. Wessels, J.M.; Foote, C.S.; Ford, W.E.; Rodgers, M.A. Photochem. Photobiol. 1997, 65, 96.
94. Michaeli, A.; Feitelson, J. Photochem. Photobiol., 1994, 59, 284.
95. Abraham, M.H.; Chadha, H.S.; Dixon, J.P.; Rafols, C.; Treiner, C. J. Chem. Soc. Perkin Trans. 2, 1995, 348.