Fragmentation of Radical Anions of Polyfluorinated Benzoates

Journal of Physical Chemistry A

Volumn 104, Issue 2, 2000, Pages 352-361

  Konovalov, Valery V ^a,d   Laev, Sergey S ^b   Beregovaya, Irina V ^b   Shchegoleva, Lyudmila N ^b   Shteingarts, Vitalij D ^b   Tsvetkov, Yuri D ^a   Bilkis, Itzhak ^c  

^a INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

^b N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^d University of Alabama   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000376764     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp993361d     Document Type: Article

References (107)

1. (a) Behar, D.; Neta, P. J. Am. Chem. Soc. 1980, 102, 4798.
2. (b) Neta, P.; Behar, D. J. Am. Chem. Soc. 1981, 103, 103.
3. (c) Behar, D.; Neta, P. J. Am. Chem. Soc. 1981, 103, 2280.
4. (a) Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J.-M.; M'Halla, F.: Savéant, J.-M. J. Am. Chem. Soc. 1980, 102, 3806.
5. (b) Andrieux, C. P.; Savéant, J.-M.; Zann, D. Nouv. J. Chim. 1984, 8, 107.
6. (a) Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
7. RNI Mechanism; American Chemical Society: Washington, DC, 1983.
8. (c) Savéant, J.-M. Acc. Chem. Res. 1980, 13, 323.
9. (d) Savéant, J.-M. Adv. Phys. Org. Chem. 1990, 26, 1.
10. (e) Savéant, J.-M. Tetrahedron 1994, 50, 10117.
11. (f) Shteingarts, V. D.; Kobrina, L. S.; Bilkis, I. I.; Starichenko, V. F. Chemistry of Polyfluoroarenes: Mechanism of Reactions, Intermediates; Nauka: Novosibirsk, 1991 (in Russian).
12. (g) Todres, Z. V. Radical Ions in Organic Synthesis; Khimiya: Moscow, 1986 (in Russian).
13. (h) Mendkovich, A. S.; Gultjai, V. P. Theoretical Aspects of Chemistry of Organic Radical Anions; Nauka: Moscow, 1990 (in Russian).
14. (a) Konovalov, V. V.; Raitsimring, A. M.; Tsvetkov, Yu. D.; Bilkis, I. I. Chem. Phys. Lett. 1989, 157, 257.
15. (b) Konovalov, V. V.; Tsvetkov, Yu. D.; Bilkis, I. I.; Laev, S. S.; Shteingarts, V. D. Mendeleev Commun. 1993, 51.
16. (a) Shchegoleva, L. N.; Bilkis, I. I.; Schastnev, P. V. Chem. Phys. 1983, 82, 343.
17. (b) Starichenko, V. F.; Shchegoleva, L. N.; Efremova, N. V.; Shteingarts, V. D.; Saik, V. O.; Schastnev, P. V. Chem. Phys. 1985, 100, 79.
18. (c) Lozovoy, V. V.; Grigoryants, V. M.; Anisimov, O. A.; Molin, Yu. N.; Schastnev, P. V.; Shchegoleva, L. N.; Bilkis, I. I.; Shteingarts, V. D. Chem. Phys. 1987, 112, 463.
19. (a) Anbar, M. Adv. Phys. Org. Chem. 1969, 7, 115.
20. (b) Freeman, P. K.; Srinivasa, R. J. Org. Chem. 1987, 52, 252.
21. Clarke, D. D.; Coulson, C. A. J. Chem. Soc. A 1969, 2, 169.
22. Parker, V. D. Adv. Phys. Org. Chem. 1983, 19, 132.
23. (a) Andrieux, C. P.; Savéant, J.-M. Electrochemical Reactions. In Investigation of Rates and Mechanisms of Reactions, Techniques of Chemistry; Bernasconi, C. F., Ed.; Wiley: NewYork, 1986; Vol. VI/4E, Part 2, p 305.
24. (b) Andrieux, C. P.; Hapiot, P.; Savéant, J.-M. Chem. Rev. 1990, 90, 723.
25. Andrieux, C. P.; Savéant. J.-M.; Tallec, A.; Tardivel, R.; Tardy, C. J. Am. Chem. Soc. 1996, 118, 9788.
26. (a) Andersen, M. L.; Mathivanan, N.; Wayner, D. D. M. J. Am. Chem. Soc. 1996, 118, 4871.
27. (b) Andersen, M. L.; Lang, W.; Wayner, D. D. M. J. Am. Chem. Soc. 1997, 119, 6590.
28. (c) Antonello, S.; Musumeci, M.; Wayner, D. D. M. J. Am. Chem. Soc. 1997, 119, 9541.
29. For a review, see ref 4e.
30. Andrieux, C. P.; Combellas, C.; Kanoufi, F.; Savéant, J.-M.; Thiébault, C. J. Am. Chem. Soc. 1997, 119, 9727.
31. Efremova, N. V.; Starichenko, V. F.; Shteingarts, V. D. Zh. Org. Khim. 1988, 24, 57.
32. (a) Amatore, C.; Combellas, C.; Pinson, J.; Oturan, M. A.; Robveille, S.; Saveant, J.-M.; Thiebault, A. J. Am. Chem. Soc. 1985, 107, 4846.
33. (b) Andrieux, C. P.; Saveant, J.-M.; Su, K. B. J. Phys. Chem. 1986, 90, 3815.
34. (c) Savéant, J.-M. J. Am. Chem. Soc. 1987, 109, 6788.
35. (d) Savéant, J.-M. J. Phys. Chem. 1994, 98, 3716.
36. •.
37. (a) Steppard, W. A.; Sharts, C. M. Organic Fluorine Chemistry; W. A. Benjamin, Inc.: New York, 1969.
38. (b) Eberson, L. Adv. Phys. Org. Chem. 1982, 18, 79.
39. Fenzlaff, M.; Illenberger, E. Chem. Phys. 1989, 136, 443.
40. Shchegoleva, L. N.; Schastnev, P. V. Zh. Fiz. Khim. 1991, 65, 1789.
41. Schastnev, P. V.; Shchegoleva, L. N. Molecular Distortions in Ionic and Excited States; CRC Press: Boca Raton, 1995.
42. aq and RA spectra and the low solubility of organic compounds.
43. (a) Barker, G. C.; Gardner, A. W.; Sammon, D. C. J. Electrochem. Soc. 1966, 113, 1182.
44. (b) Pleskov, Yu. V.; Rotenberg, Z. A.; Eletsky, V. V.; Lakomov, V. I. Discuss. Faraday Soc. 1974, 56, 52.
45. (c) Gurevich, Yu. Ya.; Pleskov, Yu. V.; Rotenberg, Z. A. Photoelectrochemistry; Plenum Press: New York, 1980.
46. (d) Benderskii, V. A.; Krivenko, A. G. Usp. Khim. 1990, 59, 3. (Engl transl: Russian Chem. Rev. 1990, 59, 1.).
47. (d) Benderskii, V. A.; Krivenko, A. G. Usp. Khim. 1990, 59, 3. (Engl transl: Russian Chem. Rev. 1990, 59, 1.).
48. (e) Benderskii. V. A.; Benderskii, A. A. Laser Electrochemistry of Intermediates; CRC Press: Boca Raton, 1995.
49. (a) Konovalov, V. V.; Tregub, V. V.; Raitsimring, A. M. Electrokhimia 1984, 20, 470.
50. (b) Konovalov, V. V.; Raitsimring, A. M.; Tsvetkov, Yu. D.; Benderskii, V. A. Chem. Phys. 1985, 93, 163.
51. (c) Konovalov, V. V.; Raitsimring, A. M.; Tsvetkov, Yu. D. J. Electroanal. Chem. 1990, 292, 33.
52. (a) Konovalov, V. V.; Raitsimring, A. M.; Tsvetkov, Yu. D. Radiat. Phys. Chem. 1988, 32, 623.
53. (b) Konovalov, V. V.; Raitsimring, A. M. Chem. Phys. Lett. 1990, 171, 326.
54. (c) Kalugin, A. I.; Konovalov, V. V.; Shokhirev, N. V.; Raitsimring, A. M. J. Electroanal. Chem. 1993, 359, 63.
55. (d) Kalugin, A. I.; Konovalov, V. V.; Raitsimring, A. M. J. Electroanal. Chem. 1993, 362, 185.
56. Konovalov, V. V.; Bilkis, I. I.; Selivanov, B. A.; Shteingarts, V. D.; Tsvetkov, Yu. D. J. Chem. Soc., Perkin Trans. 2 1993, 1707.
57. (a) Hapiot, P.; Konovalov, V. V.; Savéant, J.-M. J. Am. Chem. Soc. 1995, 117, 1428.
58. (b) Gonzales, J.; Hapiot, P.; Konovalov, V. V.; Savéant, J.-M. J. Am. Chem. Soc. 1998, 120, 10171.
59. 27b,c
60. (b) The electrode potential for hydrogen evolution in aqueous solutions at mercury electrode is about -2.0 V (SCE).
61. 27c
62. (d) Bartle, W. W.; Eggins, B. R. J. Polarog. Soc. 1966, 12, 89.
63. (e) von Stackelberg, M.; Stracke, W. Z. Electrochem. 1949, 53, 118.
64. 33b
65. (b) Swallow, A. J. Radiation Chemistry; Longman: London, 1973; p 148.
66. 29c
67. (b) Shchegoleva, L. N.; Beregovaya, I. V.; Schastnev, P. V. Magn. Resonan. and Relat. Phenom. (Vol. II, Proc. Joint 29th AMPER -13th ISMAR Conference, Berlin) 1998, 889.
68. (c) Shchegoleva, L. N.; Bliznyuk, A. A. Unpublished results.
69. c values had not been determined for all polyfluorinated benzoates, the problem connecting the rates and the regioselectivity of RAs fragmentation remained unsolved, and the fragmentation trends had not been rationalized.
70. Melting points were determined with a Kotler apparatus and are uncorrected.
71. Aldrich 1998-1999, Catalog Handbook of Fine Chemicals; Aldrich Chemical Co.: Milwaukee, 1998.
72. Holland, D. G.; Moore, G. J.; Tamborski, C. J. Org. Chem. 1964, 29, 3042.
73. Tamborski, C.; Soloski, E. J. J. Org. Chem. 1966, 31, 746.
74. Deacon, G. B.; Phillips, R. J. Aust. J. Chem. 1978, 31, 1709.
75. Bergmann, E. D.; Bercovic, S. J. Org. Chem. 1961, 26, 919.
76. Minor, J. T.; Vanderwerf, C. A. J. Org. Chem. 1952, 17, 1425.
77. Shtark, A. A.; Chuikova, T. V.; Selivanova, G. A.; Shteingarts, V. D. Zh. Org. Khim. 1987, 23, 2574.
78. Roe, A.; Little, W. F. J. Org. Chem. 1955, 20, 1577.
79. Pozdnyakovich, Yu. V.; Shteingarts, V. D. J. Fluorine Chem. 1974, 4, 317.
80. Finger, G. C.; Gortatowski, M. J.; Shiley, R. H.; White, R. H. J. Am. Chem. Soc. 1959, 81, 94.
81. Yakobson, G. G.; Odinokov, V. N.; Vorozhtsov, N. N. Zh. Obshchei Khim. 1966, 36, 139.
82. Laev, S. S.; Shteingarts, V. D.; Bilkis, I. I. Tetrahedron Lett. 1995, 36, 4655.
83. Kobrina, L. S.; Yakobson, G. G. Zh. Obshchei Khim. 1965, 35, 2055.
84. Laev, S. S.; Shteingarts, V. D. Tetrahedron Lett. 1997, 38, 3765.
85. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
86. Plakhutin, B. N. SFQP-23, Informational Materials of a Specialized Fund of Quantum Chemical Programs (SFQP) of Siberian Branch of the Academy of Sciences of USSR; Institute of Chemical Kinetics and Combustion: Novosibirsk, 1989; Vol. 3, p 16 (in Russian).
87. Gorb, L. G.; Abronin, I. A. SFQP-49 1989, 3, 22 (in Russian).
88. Schaftenaar, G. QCPE-619.
89. 50c can be assumed as typical.
90. (b) Simic, M.; Hoffman, M. Z. J. Phys. Chem. 1972, 76, 1398.
91. (c) Shoute, L. C. T.; Mittal, J. P. J. Phys. Chem. 1993, 97, 379.
92. Compton, R. G.; Harding, M. S.; Pluck, M. R.; Atherton, J. H.; Brennan, C. V. J. Phys. Chem. 1993, 97, 10416.
93. Hart, E. J.; Anbar, M. Hydrated electron; Wiley: New York, 1970.
94. Konovalov, V. V.; Bilkis, I. I.; Laev, S. S.; Raitsimring, A. M. In Proceeding of 5th Working Meeting on Radiation Interaction; Leipzig, 1990; p 204.
95. 54c
96. (b) Kishan, L. H.; Kanchan, G. Tetrahedron Lett. 1986, 27, 1371.
97. (c) Gerson, F.; Geseheidt, G.; Haring, P.; Mazur, Y.; Freeman, D.; Spreitzer, H.; Daub, J. J. Am. Chem. Soc. 1995, 117, 11861.
98. (d) Hu, Ch.-M.; Long, F.; Xu, Ze-Qi J. Fluorine Chem. 1990, 48, 29.
99. (e) Krasnov, V. I.; Platonov, V. E. Zh. Org. Khim. 1993, 29, 1078.
100. 50b,55c
101. (b) Mishra S. P.; Symons, M. C. R. J. Chem. Soc., Perkin Trans. 2 1981, 185.
102. (c) Dorfman, L. M. Acc. Chem. Res. 1970, 3, 224.
103. Here and later, an index in parentheses designates the position of primary SOMO localization.
104. Bersuker, I. B.; Gorinchoi, N. N.; Polinger, V. Z. Multielectron Problem in Quantum Chemistry; Kiev: Nauk, Dumka, 1987 (in Russian).
105. These states are of the same symmetry as the lower Σ*(p) state, which generally makes their direct calculation impossible within the framework of the Hartree-Fock (HF) approximation. Nevertheless, due to the distinction between spatial SOMO localization in different Σ*(j) states (up to 75% of the unpaired electron density is concentrated on the C-F bond in the jth position) in some cases (Table 2) it is possible to obtain self-consistent field HF solutions corresponding to the individual Σ*(j) states (see also Experimental section).
106. Gorb, L. G.; Abronin, I. A.; Khartchevnikova, N. V.; Zhidomirov, G. M. Zh. Fiz. Khim. 1984, 58, 9.
107. CF value.