Structure and reactivity of radical ions: New twists on old concepts

Chemistry - A European Journal

Volumn 12, Issue 27, 2006, Pages 7018-7026

  Donoghue, Patrick J ^a   Wiest, Olaf ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Electron transfer; Hydrocarbons; Pericyclic reaction; Radical ions; Reaction mechanisms

Indexed keywords

DELOCALIZATION; ELECTRON TRANSFER; PERICYCLIC REACTIONS; RADICAL IONS;

BONDING; ELECTRONIC STRUCTURE; HYDROCARBONS; ORGANIC COMPOUNDS; POSITIVE IONS; REACTION KINETICS;

ELECTRON TRANSITIONS;

CATION; FREE RADICAL; HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METHODOLOGY; ORGANIC CHEMISTRY; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

CATIONS; CHEMISTRY, ORGANIC; CYCLIZATION; FREE RADICALS; HYDROCARBONS; HYDROCARBONS, CYCLIC; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 33749031858     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600554     Document Type: Article

References (107)

1. For an overview of the most striking examples, compare: H. Hopf, Classics in Hydrocarbon Synthesis, Wiley-VCH, Weinheim, 1999.
2. For example: a) S. J. Cyvin, Theory of Coronoid Hydrocarbons, Springer, Berlin 1991;
3. b) P. von R. Schleyer, Chem. Rev. 2001, 101, 1115-1118 and other contributions in this special issue on aromaticity.
4. a) R. B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 1965, 87, 395-397.;
5. b) H. C. Longuet-Higgins, E. W. Abrahamson, J. Am. Chem. Soc. 1965, 87, 2045-2046;
6. c) R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-869;
7. Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
8. a) B. K. Carpenter, Acc. Chem. Res. 1992, 25, 520-528;
9. b) B. K. Carpenter, Angew. Chem. 1998, 110, 3532-3543;
10. Angew. Chem. Int. Ed. 1998, 37, 3341-3350.
11. a) A. Sancar, Chem. Rev. 2003, 103, 2203-2238;
12. b) C. B. Harrison, L.L. O'Neil, O. Wiest, J. Phys. Chem. A 2005 109, 7001-7012;
13. c) N. J. Saettel, O. Wiest, J. Am. Chem. Soc. 2001, 123, 2693-2694.
14. a) K. N. Houk, J. Gonzalez, Y. Li, Acc. Chem. Res. 1995, 28, 81-90;
15. b) O. Wiest, K. N. Houk, Top. Curr. Chem. 1996 183, 1-24;
16. c) K. N. Houk, Y. Li, J.D. Evanseck, Angew. Chem. 1992, 104, 711-739;
17. Angew. Chem. Int. Ed. Engl. 1992, 31, 682-708.
18. a) I. R. Dunkin, Tetrahedron, 1985, 41, 145-161;
19. b) N.L. Bauld, J. Cessac, J. Am. Chem. Soc. 1977, 99, 23-26;
20. c) M. J. Bishop, I. Fleming, J. Chem. Soc. C 1969, 1712.
21. D. J. Bellville, N. L. Bauld, R. Pabon, S. A. Gardner, J. Am. Chem. Soc. 1983, 105, 3584-3588.
22. E. Steckhan, J. Mlcoch, Tetrahedron Lett. 1987, 28, 1081-1084.
23. H. A. Jahn, E. Teller, Proc. R. Soc. London Ser. A 1937, 161, 220-235.
24. J. N. Aebischer, T. Bally, K. Roth, E. Haselbach, F. Gerson, X.-Z. Qin, J. Am. Chem. Soc. 1989, 111, 7909-7914.
25. O. Wiest, J. Am. Chem. Soc. 1997, 119, 5713-5719.
26. I. B. Bersuker, Chem. Rev. 2001, 101, 1067-1114.
27. a) P. Jungwirth, P. Čársky, T. Bally, J. Am. Chem. Soc. 1993, 115, 5776-5782;
28. b) V. Hrouda, T. Bally, P. Čársky, P. Jungwirth, J. Phys. Chem. A 1997, 101, 3918-3924;
29. c) F. Williams, Radiat. Phys. Chem. 2003, 67, 211-218;
30. d) T. Bally, L. Truttam, S. Dai, F. Williams, J. Am. Chem. Soc. 1995, 117, 7916-7922.
31. D. J. Bellville, R. Chelsky, N. L. Bauld, J. Comput. Chem. 1982, 3, 548-551.
32. a) G. N. Sastry, T. Bally, V. Hrouda, P. Čársky, J. Am. Chem. Soc. 1998, 120, 9323-9334;
33. b) V. Barone, N. Rega, T. Bally, G. N. Sastry, J. Phys. Chem. A 1999, 103, 217-219.
34. a) H. E. Zimmerman, Acc. Chem. Res., 1971, 4, 272-280;
35. b) M. J. S. Dewar, Angew. Chem. 1971, 83, 859-875;
36. Angew. Chem. Int. Ed. Engl. 1971, 10, 761-776.
37. For an overview, see; A.D. Allen, T.T. Tidwell, Chem. Rev. 2001, 101, 1333-1348.
38. O. Wiest, J. Phys. Chem. A 1999, 103, 7907-7911.
39. B. R. Beno, K. N. Houk, D. A. Singleton, J. Am. Chem. Soc. 1996, 118, 9984-9985.
40. a) S. Kadota, K. Tsubono, K. Makino, M. Takeshita, T. Kikuchi, Tetrahedron Lett. 1987, 28, 2857-2860;
41. b) B. Harirchian, N. L. Bauld, J. Am. Chem. Soc. 1989, 111, 1826-1828;
42. c) E. Marshall Wilson, J. G. Dietz, T. A. Shepherd, D. M. Ho, K. A. Schnapp, R. C. Elder, J. W. Watkins, L. S. Geraci, C. F. Campana, J. Am. Chem. Soc. 1989, 111, 1749-1754.
43. a) J. Mattay, G. Trampe, J. Runsick, Chem. Ber. 1988, 121, 1991-2005;
44. b) J. Mattay, J. Gersdorf, J. Mertes, J. Chem. Soc. Chem. Commun. 1985, 1088-1090;
45. c) J. Gersdorf, J. Mattay, J. Photochem. 1985, 28, 405-411;
46. d) Y. Otsuji, Kokagaku 1997, 11, 20-24.
47. a) H. Schmittel, H. von Seggern, Angew. Chem. 1991, 103, 981-983;
48. Angew. Chem. Int. Ed. Engl. 1991, 30, 999-1001;
49. b) H. Sehmittel, H. von Seggern, J. Am. Chem. Soc. 1993, 115, 2165-2177;
50. c) M. Schmittel, C. Wöhrle, Tetrahedron Lett. 1993, 34, 8431-8434.
51. a) N. L. Bauld, D. X. Gao, J. Chem. Soc. Perkin Trans. 2 2000, 931-934;
52. b) N. L. Bauld, J. K. Yang, Tetrahedron Lett. 1999, 40, 8519-8522.
53. a) O. Wiest, E. Steckhan, Tetrahedron Lett. 1993, 34, 6391-6394;
54. b) N.J. Saettel, O. Wiest, D. A. Singleton, M. P. Meyer, J. Am. Chem. Soc. 2002, 124, 11552-11559.
55. a) M. Hofmann, H. F. Schaefer, J. Am. Chem. Soc. 1999, 121, 6719-6729;
56. b) M. Hofmann, H. F. Schaefer, J. Phys. Chem. A 1999, 103, 8895-8905;
57. c) U. Haberl, E. Steckhan, O. Wiest, J. Am. Chem. Soc. 1999, 121, 6730-6736;
58. d) U. Haberl, E. Steckhan, O. Wiest, S. Blechert, Chem. Eur. J. 1999, 5, 2859-2865;
59. e) H. Hu, P. G. Wenthold, J. Phys. Chem. A 2002, 106, 10550-10553;
60. f) D. J. Goebbert, X. Liu, P.G. Wenthold, J. Am. Soc. Mass Spectrom. 2004, 15, 114-120;
61. g) W.J. van der Hart, Int. J. Mass Spectrom. 2001, 208, 119-125;
62. h) G. Bouchoux, J.-Y. Salpin, M. Yanez, J. Phys. Chem. A 2004, 108, 9853-9862;
63. i) G. Bouchoux, M. T. Nguyen, J.-Y. Salpin, J. Phys. Chem. A 2000, 104, 5778-5786.
64. a) D. W. Reynolds, B. Harirchian, H. S. Chiou, B. K. Marsh, N. L. Bauld, J. Phys. Org. Chem. 1989, 2, 57-88;
65. b) N. L. Bauld, B. Harirchian, D. W. Reynolds, J. White, J. Am. Chem. Soc. 1988, 110, 8111-8117.
66. E. Goldstein, B. Beno, K. N. Houk, J. Am. Chem. Soc. 1996, 118, 6036-6043.
67. P. Caramella, P. Quadrelli, L. Toma, S. Romano, K. S. Khuong, B. Northrop, K. N. Houk, J. Org. Chem. 2005, 70, 2994-3008.
68. For experimental studies, see: a) J. P. Dinnocenzo, D. A. Conlon, J. Am. Chem. Soc. 1988, 110, 2324-2325;
69. b) J.P. Dinnocenzo, D.A. Conlon, Tetrahedron Lett. 1995, 36, 7415-7418;
70. c) J. P. Dinnocenzo, M. Schmittel, J. Am. Chem. Soc. 1987, 109, 1561-1562;
71. d) G. Bouchoux, J. Y. Salpin, M. Yanez, J. Phys. Chem. A 2004, 108, 9853-9862;
72. e) S. Furmeier, J.O. Metzger, J. Am. Chem. Soc. 2004, 126, 14485-14492.
73. For computational studies, see: a) J. Oxgaard, O. Wiest, J. Am. Chem. Soc. 1999, 121, 11531-11537;
74. b) M. Hofmann, H. F. Schae fer, J. Mol. Struct. 2001, 599, 95-116;
75. c) T. Herbertz, H. D. Roth, J. Am. Chem. Soc. 1998, 120, 11904-11911.
76. M. Uchiyam̄a, T. Tomioka, A. Amano, J. Phys. Chem. 1964, 68, 1878-1881.
77. a) K. B. Wiberg, W. K. B. Rosenberg, P. R. Rablen, J. Am. Chem. Soc. 1991, 113, 2890-2898;
78. b) A. Karpfen, C. H. Choi, M. Kertesz, J. Phys. Chem. A 1997, 101, 7426-7433.
79. a) L. R. Pratt, C. S. Hsu, D. Chandler, J. Chem. Phys. 1978, 68, 4202-4212;
80. b) M. E. Squillacote, R. S. Sheridan, O. L. Chapman, F. A. L. Anet, J. Am. Chem. Soc. 1979, 101, 3657-3659;
81. c) W. A. Herrebout, B. J. van der Veken, A. Wang, J. R. Durig, J. Phys. Chem. 1995, 99, 578-585;
82. d) M.A. Murcko, H. Castejon, K. B. Wiberg, J. Phys. Chem. 1996, 100, 16162-16168.
83. S. Shih, R. J. Buenker, S. D. Peyerimhoff, Chem. Phys. Lett. 1972, 16, 244-251.
84. M. E. Squillacote, F. Liang, J. Org. Chem. 2005, 70, 6564-6573.
85. For reviews, see: a) A. D. Kachkovskii, Theor. Exp. Chem. 2005, 41, 139-164;
86. b) P. Frere, P. J. Skabara, Chem. Soc. Rev. 2005, 34, 69-98;
87. c) G. Wegner, Contemp. Top. Polym. Sci. 1984, 5, 281-319.
88. a) J. Oxgaard, O. Wiest, J. Phys. Chem. A 2002, 106, 3967-3974;
89. b) T. Bally, G.N. Sastry, J. Phys. Chem. A 1997, 101, 7923-7925;
90. c) G. N. Sastry, T. Bally, V. Hrouda, P. Carsky, J. Am. Chem. Soc. 1998, 120, 9323-9334.
91. J. Oxgaard, O. Wiest, J. Phys. Chem. A 2001, 105, 8236-8240.
92. J. Oxgaard, O. Wiest, unpublished results
93. a) M. Traetteberg, P. Bakken, H. Hopf, R. Haenel, Chem. Ber. 1994, 127, 1469-1478;
94. b) M. Traetteberg, H. Hopf, H. Lipka, R. Haenel, Chem. Ber. 1994, 127, 1459-1467.
95. In cases in which simple saturated hydrocarbons are oxidized, for example, by ionizing radiation, or if they are studied computationally, their structure resembles nonclassical carbocations. This can be rationalized by considering the similar energy level of the carbon-carbon single bonds that can lead to strong overlap of the unoccupied orbital with the occupied o-orbitals of the carbon-carbon single bonds.
96. a) S. C. Richtsmeier, P. G. Gassman, D. A. Dixon, J. Org. Chem. 1985, 50, 311-317;
97. b) H. D. Roth, M. L. M. Schilling, P. G. Gassman, J. L. Smith, J. Am. Chem. Soc. 1984, 106, 2711-2712.
98. T. Bally, J. Mol. Struct.: THEOCHEM 1991, 227, 249-264.
99. D. Scheschkewitz, H. Amii, H. Gornitzka, W. W. Schoeller, D. Bourissou, G. Bertrand, Science 2002, 295, 1880-1881.
100. N. J. Saettel, O. Wiest, J. Org. Chem. 2003, 68, 4549-4552.
101. H. Hopf, H. Lipka, M. Traetteberg, Angew. Chem. 1994, 106, 232-233;
102. Angew. Chem. Int. Ed. Engl. 1994, 55, 204-205.
103. For overviews of these attempts, see: a) T. Linker, M. Schmittel, Radikale und Radikalionen in der Organischen Synthese, Wiley-VCH, Weinheim, 1998;
104. b) M. Schmittel, A. Burghart, Angew. Chem. 1997, 109, 2658-2699;
105. Angew. Chem. Int. Ed. Engl. 1997, 36, 2551-2589;
106. c) N. L. Bauld, in Advances in Electron Transfer Chemistry Vol.2 (Ed.: P. S. Mariano), JAI, New York 1992, p. 1
107. d) M. Schmittel, M. K. Ghorai in: Electron Transfer in Chemistry, Vol. 2: Organic and Metalorganic Systems (Eds.: J. Mattay, D. Astruc), Wiley-VCH New York 2001 as well as other contributions in this volume.