Photo- and radiation-chemical generation and thermodynamic properties of the aminium and aminyl radicals derived from N-phenylglycine and (N-chloro,N- phenyl)glycine in aqueous solution: Evidence for a new photoionization mechanism for aromatic amines

Chemistry - A European Journal

Volumn 5, Issue 4, 1999, Pages 1192-1201

  Canle, M L ^a,b   Santaballa, J A ^b   Steenken, S ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^b UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

Amino acids; Laser chemistry; Photoionization; Radical ions; Radiochemistry; Redox chemistry

Indexed keywords

AROMATIC AMINE; GLYCINE DERIVATIVE; PHENYLGLYCINE; RADICAL;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; IONIZATION; PHOTOCHEMISTRY; RADIOCHEMISTRY; THERMODYNAMICS;

EID: 0032893433     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990401)5:4<1192::AID-CHEM1192>3.0.CO;2-M     Document Type: Article

References (135)

1. a) Y. L. Chow, Aminium Radicals, in Reactive Intermediates, Vol. 1 (Ed.: R. A. Abramovitch), Plenum, New York, 1980, pp. 151-262;
2. b) N. J. Pienta, Amines, Thiols, and Thioethers: Heteroatomic Electron Donors, in Photoinduced Electron Transfer. Part C: Photoinduced Electron Transfer Reactions: Organic Substrates (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, pp. 421-486;
3. c) J. K. Dohrmann, Proton and Electron Transfer. Biradicals, in Radical Reaction Rates in Liquids. Landolt-Börnstein. Numerical Data and Functional Relationships in Science and Technology, Subvol. e, Vol. 13 (Ed.: H. Fischer), Springer, Berlin, 1995, pp. 87-92;
4. d) L. J. Mittal, J. P. Mittal, J. Photochem. Photobiol. A 1997, 106, 127;
5. e) G. Merényi, J. Lind, Anilinyl Radicals, in N-Centered Radicals (Ed.: Z. Alfassi), Wiley, London, 1998.
6. a) M. E. Wolff, Chem. Rev. 1963, 63, 55;
7. b) J. Spanswick, K. U. Ingold, Can. J. Chem. 1970, 48, 546;
8. c) M. Simic, E. J. Hayon, J. Am. Chem. Soc. 1971, 93, 5982;
9. d) R. W. Fessenden, P. Neta, J. Phys. Chem. 1972, 76, 2857;
10. e) Y. L. Chow, Acc. Chem. Res. 1973, 6. 354;
11. f) A. J. Cessna, S. E. Sugamori, R. W. Yip, M. P. Lau, R. S. Snyder, Y. L. Chow, J. Am. Chem. Soc. 1977, 99, 4044;
12. g) R. W. Yip, T. Vidoczy, R. S. Snyder, Y. L. Chow, J. Phys. Chem. 1978, 82, 1194.
13. a) F. D. Lewis, Acc. Chem. Res. 1986, 19, 401;
14. b) T. G. Waddell, T. J. Miller, Origins Life Evol. Biosphere 1992, 21, 219;
15. c) J. Lind, M. Jonsson, T. E. Eriksen, G. Merényi, J. Phys. Chem. 1993, 97, 1610;
16. d) X. Zhang, S. R. Yeh, S. Hong, M. Freccero, A. Albini, D. E. Falvey, P. S. Mariano, J. Am. Chem. Soc. 1994, 116, 4211;
17. e) P. Maslak, W. H. Chapman, T. M. Vallombroso, B. A. Watson. J. Am. Chem. Soc. 1995, 117, 12380;
18. f) R. D. Burton, M. D. Bartberger, Z. Zhang, J. R. Ezler, K. S. Schanze, J. Am. Chem. Soc. 1996, 118, 565;
19. g) B. D. Wagner, G. Ruel, J. Lusztyk, J. Am. Chem. Soc. 1996, 118, 13;
20. h) E. R. Gaillard, D. G. Whitten, Acc. Chem. Res. 1996, 29, 292.
21. a) L. J. Mittal, J. P. Mittal, E. Hayon, Chem. Phys. Lett. 1973, 18, 319;
22. b) L. J. Mittal, J. P. Mittal, E. Hayon, J. Phys. Chem. 1973, 77, 1620;
23. c) L. J. Mittal, J. P. Mittal, E. Hayon, J. Am. Chem. Soc. 1973, 95, 6203;
24. d) K. M. Schaich. Free Radical Initiation in Proteins and Amino Acids by Ionizing and Ultraviolet Radiations and Lipid Oxidation. Part I: Ionizing Radiation, Vol 13. (Ed.: K. M. Schaich), CRC, 1980, pp. 88-129;
25. e) D. N. Nikogosyan, H. Görner, J. Photochem. Photobiol. B: Biol. 1995, 30, 189.
26. L. I. Grosswiner, Curr. Top. Radiat. Res. Q. 1976, 11, 141.
27. a) E. M. Thurmann, Organic Geochemistry of Natural Waters, Martinus Nijhoff (The Netherlands) 1985;
28. b) Biohazards of Drinking Water Treatment (Ed. R. A. Larson), Lewis, Chelsea, 1990, p. 138;
29. c) R. A. Larson, E. J. Weber, Reaction Mechanisms in Environmental Organic Chemistry, Lewis, Boca Ratón, 1994.
30. a) E. A. Bryant, G. P. Fulton, G. C. Budd, Disinfection Alternatives for Safe Drinking Water, Van Nostrand Reinhold, New York, 1992;
31. b) S. Miller, Environ. Sci. Technol. 1993, 27, 2292;
32. c) A. Newman, Environ. Sci. Technol. 1993, 27, 2295;
33. d) W. H. Glaze, AWWA Research Foundation Workshop Report, 1993.
34. C. Le Cloirec, G. Martin, Water Chlorination. Environmental Impact and Health Effects, Vol. 5, Lewis, Chelsea, 1985, p. 821.
35. a) J. G. Smith, J. Chem. Ed. 1975, 52, 656;
36. b) R. J. Bull, L. J. McCabe, Water Chlorination. Environmental Impact and Health Effects, Vol. 5, Lewis, Chelsea, 1985, p. 111;
37. c) M. S. Masri, Food Chem. Toxicol. 1985, 24, 923;
38. d) G. Reynolds, R. Mekras, N. Perry, N. Graham, Environ. Technol. Lett. 1989, 10, 591;
39. e) A.C. Sen, J. Owusu-Yaw, W. B. Wheeler, C. I. Wei, J. Food Sci. 1989, 54, 1057;
40. f) J. Owusu-Yaw, W. B. Wheeler, C. I. Wei, Water Chlorination. Environmental Impact and Health Effects, Vol. 6, Lewis, Chelsea, 1990, p. 179;
41. g) R. Frazén, L. Kronberg, Environ. Sci. Technol. 1994, 28, 2222;
42. h) T. Soldi, V. Riganti, A. Profumo, O. Conio, Microbiol. Aliments Nutr. 1994, 12, 371;
43. i) E. Eder, E. Weinfurtner, Chemosphere 1994, 29, 2455;
44. j) D. Henschler, Angew. Chem. 1994, 106, 1997; Angew. Chem. Int. Ed. Engl. 1994, 33, 1920;
45. j) D. Henschler, Angew. Chem. 1994, 106, 1997; Angew. Chem. Int. Ed. Engl. 1994, 33, 1920;
46. k) R. J. Bull, L. S. Birnbaum, K. P. Cantor, J. B. Rose, B. E. Butterworth, R. Pegram, J. Tuomisto, Fundam. Appl. Toxicol. 1995, 28, 155;
47. l) W. A. Prütz, Arch. Biochem. Biophys. 1996, 332, 110.
48. a) X. L. Armesto, M. Canle L., M. V. García, J. A. Santaballa, Chem. Soc. Rev. 1998, 28, 453. and references therein;
49. b) L. Abia, X. L. Armesto, M. Canle L., M. V. García, J. A. Santaballa, Tetrahedron. 1998, 54, 521;
50. c) X. L. Armesto, M. Canle L., M. V. García, M. Losada, J. A. Santaballa, J. Phys. Org. Chem. 1996, 9, 552;
51. d) M. Canle L., Mecanismos de Cloración de α-Aminoácidos y de Fragmentación de (N-X)-α-Aminoácidos (ISBN 84-605-2057-9) Santiago de Compostela, 1994;
52. e) X. L. Armesto, M. Canle L., M. Losada, J. A. Santaballa, J. Org. Chem. 1994, 59, 4659;
53. f) X. L. Armesto, M. Canle L., A.M. Gamper, M. Losada, J. A. Santaballa. Tetrahedron. 1994, 50, 10509;
54. g) X. L. Armesto, M. Canle L., J. A. Santaballa, Tetrahedron. 1993, 49, 275.
55. a) S. O. Nawaukwa, P. M. Keehm, Tetrahedron Lett. 1982, 23, 3135;
56. b) D. A. Reckhow, P. C. Singer, Water Chlorination. Environmental Impact and Health Effects, Vol. 5, Lewis, New York, 1985, 1229.
57. a) T. L. Krause, C. T. Anderson, D. R. Masterton, J. D. Seyfert, Disinfection: Is Chlorination Still the Best Answer?, 53th Annual Conference of the WPCF, Las Vegas, 1980;
58. b) L. Metcalf, H. P. Eddy, Wastewater Engineering. Treatment, Disposal, Reuse, McGraw Hill, New York, 1995;
59. c) F. J. Beltrán, M. González, J. F. González. Water Res. 1997, 31, 2405.
60. a) R. Pocklington, Nature 1971, 230, 374;
61. b) B. Haake, V. Ittekkot, V. Ramaswamy, R. R. Nair, S. Honjo, Mar. Chem. 1992, 40, 291;
62. c) see ref. [7].
63. K. Verschueren, Handbook of Environmental Data on Organic Chemicals, 3rd ed., Van Nostrand Reinhold, New York, 1996.
64. Merck Index, 16th ed., Merck, Rahway, 1983.
65. V. M. Correia, T. Stephenson, S. J. Judd, Environ. Technol. 1994, 15, 917, and references therein.
66. C. D. McCullough (Horsell Graphic Industries), U.K. Pat. Appl. GB 2304719 A1. 1997;
67. Chem. Abstr. 1997, 127, 42287.
68. D. M. Stanbury, Adv. Inorg. Chem. 1989, 33, 69.
69. 0 taken from ref. [43].
70. - E′ = 1.68 V vs. NHE.
71. 0 taken from ref. [43].
72. A. Nadezhdin, H. B. Dunford, Can. J. Biochem. 1979, 57, 1080.
73. 0 taken from ref. [43].
74. G. Nord, B. Pedersen, E. Floryan-Lovborg, P. Pagsberg, Inorg. Chem. 1982, 21, 2327.
75. 0 taken from ref. [43].
76. M. S. Ram, D. M. Stanbury, Inorg. Chem. 1985, 24, 4233.
77. H. A. Schwarz, B. H. J. Bielski, J. Phys. Chem. 1986, 90, 1445.
78. 0 taken from ref. [43].
79. M. Jonsson, J. Lind, T. E. Eriksen, G. Merényi, J. Am. Chem. Soc. 1994, 116, 1423.
80. 0 taken from ref. [43].
81. S. Steenken, unpublished results.
82. V. M. Berdnikov, N. M. Bazhin, Russ. J. Phys. Chem. 1970, 44, 395.
83. S. A. Rice, Diffussion Limited Reactions, in Comprehensive Chemical Kinetics, Vol. 25, (Eds.: C. H. Bamford, C. F. H. Tipper, R. G. Compton), Elsevier, Amsterdam, 1985.
84. R. A. McClelland, V. M. Kanagasabapathy, N. S. Banait, S. Steenken, J. Am. Chem. Soc. 1991, 113, 1009.
85. L. Qin, G. N. R. Tripathi, R. H. Schuler, Z. Naturfosch. A 1985, 40, 1026.
86. M. Jonsson, J. Lind, G. Merényi, T. E. Eriksen, J. Chem. Soc. Perkin Trans. 2. 1995, 61.
87. F. G. Bordwell, X. M. Zhang, J. P. Cheng, J. Org. Chem. 1993, 58, 6410.
88. S. Steenken, Free Radical Res. Commun. 1992, 16, 349.
89. a) W. C. Danen, T. T. Kensler, J. Am. Chem. Soc. 1970, 92, 5235;
90. b) W. C. Danen, R. C. Rickard, J. Am. Chem. Soc. 1972, 94, 3254.
91. E. J. Land, G. Porter, Trans. Faraday Soc. 1963, 59, 2027.
92. a) R. A. Marcus, A. O. Cohen, J. Phys. Chem. 1968, 72, 4249;
93. b) J. R. Murdoch, J. Am. Chem. Soc. 1972, 94, 4410;
94. c) H. F. Gilbert, W. P. Jencks, J. Am. Chem. Soc. 1977, 99, 7931;
95. d) H. Fischer, F. X. De Candis, S. D. Ogden, W. P. Jencks, J. Am. Chem. Soc. 1980, 102, 1340;
96. e) R. A. Bednar, W. P. Jencks, J. Am. Chem. Soc. 1985, 107, 7117;
97. f) F. Hibbert, Adv. Phys. Org. Chem. 1986, 22, 113.
98. J. P. Guthrie, J. Am. Chem. Soc. 1996, 118, 12886.
99. CRC Handbook of Chemistry and Physics, 76th ed. (Ed.: D. R. Lide), CRC, Boca Ratón, 1996.
100. 1. M. Eigen. Angew. Chem. 1963, 75, 489; Angew. Chem. Int. Ed. Engl. 1964, 3, 1.
101. 1. M. Eigen. Angew. Chem. 1963, 75, 489; Angew. Chem. Int. Ed. Engl. 1964, 3, 1.
102. 2- were present in 99% and observing the deprotonation simultaneously, the pH was set at an intermediate value between both species and the percentage of each one calculated for each concentration.
103. Promethazine is a common name for 10-(2-dimethylaminopropyl)-phenothiazine.
104. P. Wardman, J. Phys. Chem. Ref. Data. 1989, 18, 1637.
105. a) S. Arai, L. M. Dorfman, Adv. Chem. Ser. 1968, 82, 378;
106. b) Ref. [47];
107. c) Ref. [29].
108. G. V. Buxton, C. L. Greenstock, W. P. Helman, A. B. Ross, J. Phys. Chem. Ref. Data. 1988, 17, 513.
109. PI values reported in this work would be rather higher.
110. PI values reported in this work would be rather higher.
111. -1 are given in: R. V. Bensasson, J. C. Gramain, J. Chem. Soc. Faraday Trans I. 1980, 76, 1801, using different assumptions that introduce some uncertainty in the values.
112. -1. Lutz, E. Breheret, L. Lindqvist, J. Phys. Chem. 1973, 77, 1758.
113. 1. J. L. Faria, S. Steenken, J. Am. Chem. Soc. 1992, 96, 10869.
114. -1 : ref. [65].
115. NCI being reported for the monophotonic part.
116. J. C. Mialocq, E. Amouyal, A. Bernas, D. Grand, J. Phys. Chem. 1982, 86, 3173.
117. Gaussian 94 (Revision A.I), M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andrés, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. González, J. A. Pople, Gaussian, Pittsburgh, 1995.
118. a) N. Bodor, J. J. Kaminski, S. D. Worley, T. H. Colton, T. H. Lee, J. W. Rabalais, J. Pharmaceutical Sci. 1974, 63, 1387;
119. b) H. M. Rosenstock, K. Draxl, B. W. Steiner, J. T. Herren, J. Phys. Chem. Ref. Data. 1977, 6, suppl. 1;
120. c) Ionisation Potential and Appearance Potential Measurements (1971-1981), U.S. Department of Commerce, National Bureau of Standards, Washington, 1982;
121. d) R. G. Pearson, J. Am. Chem. Soc. 1986, 108, 6109.
122. a) F. Saito, S. Tobita, H. Shizuka, J. Photochem. Photobiol A. 1997, 106, 119.
123. T. P. Debies, J. W. Rabalais, J. Electron Spectrosc. 1972/73, 1, 355.
124. a) P. F. De Violet, Rev. Chem. Intermed. 1981, 4, 121;
125. b) M. Braun, J. Y. Fan, W. Fuss, K. L. Kompa, G. Müller, W. E. Schinid, Methods in Laser Spectroscopy (Eds.: Z. Prior, A. Ben-Reuven, M. Rosenbluh), Plenum Press, New York, 1986.
126. a) Y. A. Malkin, S. Ruziev, V. A. Kuz'min, J. Gen. Chem. USSR. 1987, 57, 560;
127. b) Y. A. Malkin, V. A. Kuz'min, Russ. Chem. Rev. 1985, 54, 1041.
128. a) R. Das, S. Mitra, D. N. Nath, S. Mukherjee, j. Chim. Phys. Phys. Chim. Biol. 1996, 93, 458;
129. b) L. Biczok, T. Berces, H. Linschitz, J. Am. Chem. Soc. 1997, 119, 11071.
130. R. A. McClelland, M. J. Kahley, P. A. Davidse, G. Hadzialic, J. Am. Chem. Soc. 1996, 118, 4794.
131. R. H. Schuler, A. L. Hartzell, B. Behar, J. Phys. Chem. 1981, 85, 192.
132. S. Steenken, J. Chem. Soc. Faraday Trans. 1. 1987, 83, 113.
133. Y. Tabata, I. Ito, S. Tagawa, Handbook of Radiation Chemistry, CRC, Boston, 1991.
134. R. A. McClelland, N. Banait, S. Steenken, J. Am. Chem. Soc. 1986, 108, 7023.
135. G. L. Hug, Natl. Stand. Ref. Data Ser. 1981, 69, 1.