Stability and Three-Dimensional Aromaticity of closo-Monocarbaborane Anions, CBn-1Hn-, and closo-Dicarboranes, C2Bn-2Hn

Inorganic Chemistry

Volumn 37, Issue 14, 1998, Pages 3454-3470

  Von Schleyer, Paul Ragué ^a,b   Najafian, Katayoun ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001604039     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic980110v     Document Type: Article

References (200)

1. (a) Lipscomb, W. N. Boron Hydrides; W. A. Benjamin, New York: 1963.
2. (b) Grimes, R. N. Carboranes; Academic Press: New York, 1970.
3. (c) Mutterties, E. L. Boron Hydride Chemistry; Academic Press: New York, 1975.
4. (d) Onak, T. Organoborane Chemistry; Academic: New York, 1975.
5. (e) Olah, G. A.; Surya Prakash, G. K.; Williams, R. E.; Field, L. D.; Wade, K. Hypercarbon Chemistry; Wiley: New York, 1987.
6. (f) Onak, T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Elsevier Science Ltd.: Oxford, U. K., 1995; Vol. 1, Chapter 6.
7. (a) Liebman, J. F.; Greenberg, A.; Williams, R. E. Advances in Boron and The Boranes; VCH Verlagsgesellschaft: New York, 1988.
8. (b) Olah, G. A.; Wade, K.; Williams, R. E. Electron Deficient Boron and Carbon Clusters; John Wiley and Sons: New York, 1991.
9. (c) Williams, R. E. In Advances in Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1994.
10. (a) Wade, K. Electron Deficient Compounds; Nelson: London, 1971.
11. (b) Minkin, V. I.; Minyaev, R. M; Zhdanov, Yu. A. Nonclassical Structures of Organic Compounds; Mir Publishers: Moscow, 1987.
12. (c) Mingos, D. M. P.; Wales, D. J. Introduction to Cluster Chemistry; Prentice Hall: Englewood Cliffs, NJ, 1990.
13. (a) Schleyer, P. v. R.; Subramanian, G.; Dransfeld, A. J. Am. Chem. Soc. 1996, 118, 9988.
14. (b) Schleyer, P. v. R.; Subramanian, G.; Jiao, H.; Najafian, K.; Hofmann, M. In Advances in Boron Chemistry; Siebert, W., Ed.; The Royal Society of Chemistry: Cambridge, England, 1997.
15. Schleyer, P. v. R.; Najafian, K. In The Borane, Carborane, Carbocation Continuum; Casanova, J., Ed.; Wiley: New York, 1998.
16. King, R. B.; Rouvray, D. H. J. Am. Chem. Soc. 1977, 99, 7834.
17. Aihara, J. J. Am. Chem. Soc. 1978, 100, 3339.
18. Hofmann, M.; Fox, M. A.; Greatrex, R.; Schleyer, P. v. R.; Bausch, J. W.; Williams, R. E. Inorg. Chem. 1996, 35, 6170.
19. Dewar, M. J. S.; McKee, M. L. Inorg. Chem. 1980, 19, 2662.
20. Gimarc, B. M.; Zhao, M. Inorg. Chem. 1996, 35, 825.
21. Ott, J. J.; Gimarc, B. M. J. Comput. Chem. 1986, 7, 673.
22. (a) Bregadze, V. I. Chem. Rev. 1992, 92, 209 and references therein.
23. (b) Plesek, J. Chem. Rev. 1992, 92, 269 and references therein.
24. (a) Zakharkin, L. I.; Pisareva, I. V.; Bikkineev, R. K. Bull. Akad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1977, 577.
25. (b) Andrews, J. S.; Zyas, J.; Jones, M., Jr. Inorg. Chem. 1985, 24, 3715.
26. (c) Albagli, D.; Zheng, G.; Jones, M., Jr. Inorg. Chem. 1986, 25, 129 and references therein.
27. Gmelin Handbook of Inorganic Chemistry, 8th ed.; Springer-Verlag: Berlin, 1988; 3rd supplement, Vol. 4.
28. Zakharkin, L. I.; Ol'shevskaya, V. A. IZV. Akad. Nauk, ser. Khim. 1995, 6, 1138.
29. (a) Hawthorne, M. F. Pure Appl. Chem. 1991, 63, 327 and references therein.
30. (b) Hawthorne, M. F. Angew Chem., Int. Ed. Engl. 1993, 32, 950.
31. (a) Sneddon, L. G.; Mirabelli, M. G.; Lynch; A. T.; Fazen, P. J.; Su, K.; Beck, J. S. Pure Appl. Chem. 1991, 63, 407.
32. (b) Getman, T. D.; Garrett, P. M.; Knobler, C. B.; Hawthorne, M. F.; Thorne, K.; MacKenzie, J. D. Organometallics 1992, 11, 2723.
33. (a) Grimes, R. N. Angew Chem., Int. Ed. Engl. 1993, 32, 1289.
34. (b) Jiang, W.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1996, 35, 3056.
35. (c) Jiang, W.; Knobler, C. B.; Hawthorne, M. F. Angew Chem., Int. Ed. Engl. 1996, 35, 2536.
36. For example, (a) Blanch, R. J.; Li, J.; Bush, L. C.; Jones, M., Jr. J. Am. Chem. Soc. 1992, 114, 9236. (b) Blanch, R. J.; Bush, L. C.; Jones, M., Jr. Inorg. Chem. 1994, 33, 198. (c) Cunningham, R. J.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1994, 33, 4811. (d) Ho, D. M.; Cunningham, R. J.; Brewer, J. A.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1995, 34, 5274. (e) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267. (f) Zharov, I.; Saxena, A.; Michl, J.; Miller, R. D. Inorg. Chem. 1997, 36, 6033. (g) Srivastava, R. R.; Singhaus, R. R.; Kabalka, G. W. J. Org. Chem. 1997, 62, 4476.
37. For example, (a) Blanch, R. J.; Li, J.; Bush, L. C.; Jones, M., Jr. J. Am. Chem. Soc. 1992, 114, 9236. (b) Blanch, R. J.; Bush, L. C.; Jones, M., Jr. Inorg. Chem. 1994, 33, 198. (c) Cunningham, R. J.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1994, 33, 4811. (d) Ho, D. M.; Cunningham, R. J.; Brewer, J. A.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1995, 34, 5274. (e) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267. (f) Zharov, I.; Saxena, A.; Michl, J.; Miller, R. D. Inorg. Chem. 1997, 36, 6033. (g) Srivastava, R. R.; Singhaus, R. R.; Kabalka, G. W. J. Org. Chem. 1997, 62, 4476.
38. For example, (a) Blanch, R. J.; Li, J.; Bush, L. C.; Jones, M., Jr. J. Am. Chem. Soc. 1992, 114, 9236. (b) Blanch, R. J.; Bush, L. C.; Jones, M., Jr. Inorg. Chem. 1994, 33, 198. (c) Cunningham, R. J.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1994, 33, 4811. (d) Ho, D. M.; Cunningham, R. J.; Brewer, J. A.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1995, 34, 5274. (e) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267. (f) Zharov, I.; Saxena, A.; Michl, J.; Miller, R. D. Inorg. Chem. 1997, 36, 6033. (g) Srivastava, R. R.; Singhaus, R. R.; Kabalka, G. W. J. Org. Chem. 1997, 62, 4476.
39. For example, (a) Blanch, R. J.; Li, J.; Bush, L. C.; Jones, M., Jr. J. Am. Chem. Soc. 1992, 114, 9236. (b) Blanch, R. J.; Bush, L. C.; Jones, M., Jr. Inorg. Chem. 1994, 33, 198. (c) Cunningham, R. J.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1994, 33, 4811. (d) Ho, D. M.; Cunningham, R. J.; Brewer, J. A.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1995, 34, 5274. (e) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267. (f) Zharov, I.; Saxena, A.; Michl, J.; Miller, R. D. Inorg. Chem. 1997, 36, 6033. (g) Srivastava, R. R.; Singhaus, R. R.; Kabalka, G. W. J. Org. Chem. 1997, 62, 4476.
40. For example, (a) Blanch, R. J.; Li, J.; Bush, L. C.; Jones, M., Jr. J. Am. Chem. Soc. 1992, 114, 9236. (b) Blanch, R. J.; Bush, L. C.; Jones, M., Jr. Inorg. Chem. 1994, 33, 198. (c) Cunningham, R. J.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1994, 33, 4811. (d) Ho, D. M.; Cunningham, R. J.; Brewer, J. A.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1995, 34, 5274. (e) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267. (f) Zharov, I.; Saxena, A.; Michl, J.; Miller, R. D. Inorg. Chem. 1997, 36, 6033. (g) Srivastava, R. R.; Singhaus, R. R.; Kabalka, G. W. J. Org. Chem. 1997, 62, 4476.
41. For example, (a) Blanch, R. J.; Li, J.; Bush, L. C.; Jones, M., Jr. J. Am. Chem. Soc. 1992, 114, 9236. (b) Blanch, R. J.; Bush, L. C.; Jones, M., Jr. Inorg. Chem. 1994, 33, 198. (c) Cunningham, R. J.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1994, 33, 4811. (d) Ho, D. M.; Cunningham, R. J.; Brewer, J. A.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1995, 34, 5274. (e) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267. (f) Zharov, I.; Saxena, A.; Michl, J.; Miller, R. D. Inorg. Chem. 1997, 36, 6033. (g) Srivastava, R. R.; Singhaus, R. R.; Kabalka, G. W. J. Org. Chem. 1997, 62, 4476.
42. For example, (a) Blanch, R. J.; Li, J.; Bush, L. C.; Jones, M., Jr. J. Am. Chem. Soc. 1992, 114, 9236. (b) Blanch, R. J.; Bush, L. C.; Jones, M., Jr. Inorg. Chem. 1994, 33, 198. (c) Cunningham, R. J.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1994, 33, 4811. (d) Ho, D. M.; Cunningham, R. J.; Brewer, J. A.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1995, 34, 5274. (e) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267. (f) Zharov, I.; Saxena, A.; Michl, J.; Miller, R. D. Inorg. Chem. 1997, 36, 6033. (g) Srivastava, R. R.; Singhaus, R. R.; Kabalka, G. W. J. Org. Chem. 1997, 62, 4476.
43. Diaz, M.; Jaballas, J.; Arias, J.; Lee, H.; Onak, T. J. Am. Chem. Soc. 1996, 118, 4405.
44. (a) Gimarc, B. M.; Ott, J. J. J. Am. Chem. Soc. 1987, 109, 1388 and references therein.
45. (b) Gimarc, B. M.; Dai, B.; Warren, D. S.; Ott, J. J. J. Am. Chem. Soc. 1990, 112, 2597.
46. (a) Kang, H. C.; Lee, S. S.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1991, 30, 2024.
47. (b) Varadarajan, A.; Johnson, S. E.; Gomez, F. A.; Chakrabarti, S.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 9003.
48. (c) Hitchock, A. P.; Wen, A. T.; Lee, S.; Glass, J. A., Jr.; Spencer, J. T.; Dowben, P. A. J. Phys. Chem. 1993, 97, 8171.
49. (a) Kang, H. C.; Do, Y.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1988, 27, 1716.
50. (b) Bandman, M. C.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1988, 27, 2399.
51. (c) Bandman, M. C.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 1989, 28, 1204.
52. (d) Edvenson, G. M.; Gaines, D. F. Inorg. Chem. 1990, 29, 1210.
53. (e) Schubert, D. M.; Rees, W. S. Jr.; Knobler, C. B.; Hawthorne, M. F., Organometallics 1990, 9, 2938.
54. (f) Manning, M. K.; Knobler, C. B.; Khattar, R.; Hawthorne, M. F. Inorg. Chem. 1991, 30, 2009.
55. (a) Müller, J.; Base, K.; Magnera, T. F.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9721.
56. (b) Getman, T. D.; Garrett, P. M.; Knobler, C. B.; Hawthorne, M. F.; Thorne, K.; MacKenzie, J. D. Organometallics 1992, 11, 2723.
57. (c) Janousek, Z.; Fusek, J.; Stibr, B. J. Chem. Soc., Dalton Trans. 1992, 17, 2649.
58. (a) Stibr, B.; Plesek, J.; Jelinek, T.; Hermanek, S.; Solntsev, K. A.; Kuznetsov, N. T. Collect. Czech. Chem. Commun. 1987, 52, 957.
59. (b) Jelinek, T.; Stibr, B.; Hermanek, S.; Plesek, J. J. Chem. Soc., Chem. Commun. 1989, 12, 804.
60. (c) Hynk, D.; Rankin, D. W. H.; Roberston, H. E.; Hofmann, M.; Schleyer, P. v. R.; Bühl, M. Inorg. Chem. 1994, 33, 4781.
61. (a) Gimarc, B. M.; Ott, J. J. Inorg. Chem. 1986, 25, 2708.
62. (b) Gimarc, B. M.; Dai, B.; Ott, J. J. J. Comput. Chem. 1989, 10, 14.
63. (a) Onak, T.; Tran, D.; Tseng, J.; Diaz, M.; Arias, J.; Herrera, S. J. Am. Chem. Soc. 1993, 115, 9210.
64. (b) Ceulemans, A.; Goijens, G.; Nguyen, M. T. J. Am. Chem. Soc. 1994, 116, 9395.
65. (c) Diaz, M.; Jaballas, J.; Tran, D.; Lee, H.; Arias, J.; Onak, T. Inorg. Chem. 1996, 35, 4536.
66. (a) Bühl, M.; Mebel, A. M.; Charkin, O. P.; Schleyer, P. v. R. Inorg. Chem. 1992, 31, 3769.
67. (b) Bausch, J. W.; Prakash, G. K. S.; Williams, R. E. Inorg. Chem. 1992, 31, 3763.
68. (c) Onak, T.; Tseng, J.; Tran, D.; Herrera, S.; Chan, B.; Arias, J.; Diaz, M. Inorg. Chem. 1992, 31, 3910.
69. (a) Bühl, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1992, 114, 477.
70. (b) Bühl, M.; Gauss, J.; Hofmann, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1993, 115, 12385.
71. (a) McKee, M. L. J. Am. Chem. Soc. 1988, 110, 5317.
72. (b) Ott, J. J.; Brown, C. A.; Gimarc, B. M. Inorg. Chem. 1989, 28, 4269.
73. (c) Nam, W.; Abdou, Z.; Lee, H.; Banuelos, T.; Onak, T. Inorg. Chem. 1989, 28, 669.
74. (d) Beltram, G. A.; Jasperse, C.; Cavanaugh, M. A.; Fehlner, T. P. Inorg. Chem. 1990, 29, 329.
75. (e) Gomez, F. A.; Onak, T.; Arias, J.; Alfonso, C. Main Group Met. Chem. 1990, 13, 237.
76. (f) McKee, M. L. J. Phys. Chem. 1992, 96, 1679.
77. (g) Timofeeva, T.; Mazurek, U.; Allinger, N. L. J. Mol. Struct. (THEOCHEM) 1996, 363, 35.
78. (a) Nam, W.; Onak, T. Inorg. Chem. 1987, 26, 158.
79. (b) Nam, W.; Onak, T. Inorg. Chem. 1987, 26, 48.
80. (c) Abdou, Z.; Gomez, F.; Abdou, G.; Onak, T. Inorg. Chem. 1988, 27, 3679.
81. (d) Tomita, H.; Luu, H.; Onak, T. Inorg. Chem. 1991, 30, 812.
82. (e) Onak, T.; Abdou, Z.; Abdou, G.; Herrera, S. Heteroat. Chem. 1992, 3, 219.
83. (f) Onak, T.; Tseng, J.; Diaz, M.; Tran, D.; Arias, J.; Herrera, S.; Brown, D. Inorg. Chem. 1993, 32, 487.
84. (a) McKee, M. L. J. Am. Chem. Soc. 1992, 114, 879.
85. (b) Slutsky, V. G.; Schleyer, P. v. R. Mendeleev Commun. 1994, 12.
86. (a) McKee, M. L. J. Phys. Chem. 1991, 95, 9273.
87. (b) McKee, M. L. J. Am. Chem. Soc. 1991, 113, 9448.
88. (c) McKee, M. L. J. Am. Chem. Soc. 1996, 118, 42l.
89. (a) Schleyer, P. v. R.; Gauss, J.; Bühl, M.; Greatrex, R. A.; Fox, M. A. J. Chem. Soc., Chem. Commun. 1993, 23, 1766.
90. (b) McKee, M. L. J. Am. Chem. Soc. 1995, 117, 8001.
91. Vondrak, T.; Hermanek, S.; Plesek, J. Polyhedron 1993, 12, 1301.
92. (a)Müller, J.; Runsik, J.; Paetzold, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 175.
93. (b) Hynk, D.; Bühl, M.; Schleyer, P. v. R.; Volden, H. V.; Gundersen, S.; Müller, J.; Paetzold, P. Inorg. Chem. 1993, 32, 2442.
94. (a) Little, J. C.; Moran, J. T.; Todd, L. J. J. Am. Chem. Soc. 1967, 89, 5495.
95. (b) Getman, T. D.; Deng, H.-B.; Hsu, L.-Y.; Shore, S. G. Inorg. Chem. 1989, 28, 3612.
96. Hynk, D.; Vajda, E.; Bühl, M.; Schleyer, P. v. R. Inorg. Chem. 1992, 31, 2464 and references therein.
97. (a) Arafat, A.; Baer, J.; Huffman, J. C.; Todd, L. J. Inorg. Chem. 1986, 25, 3757.
98. (b)Bühl, M.; Schleyer, P. v. R.; Havlas, Z.; Hynk, D.; Hermanek, S. Inorg. Chem. 1991, 30, 3107.
99. Pretzer, W. R.; Rudolph, R. W. J. Am. Chem. Soc. 1973, 95, 931.
100. (a) Stibr, B. Chem. Rev. 1992, 92, 225.
101. (b) Strauss, S. H. Chem. Rev. 1993, 93, 927.
102. (a) Knoth, W. H. J. Am. Chem. Soc. 1967, 89, 1274.
103. (b) Knoth, W. H.; Little, J. L.; Lawrence, J. R.; Scholer, F. R.; Todd, L. J. Inorg. Synth. 1968, 11, 33.
104. (c) Knoth, W. H. Inorg. Chem. 1971, 10, 598.
105. Wiersema, R. J.; Hawthorne, M. F. Inorg. Chem. 1973, 12, 785.
106. Plesek, J.; Jelínek, T.; Stíbr, B.; Hermánek, S. J. Chem. Soc., Chem. Commun. 1988, 348.
107. Jelínek, T.; Stíbr, B.; Plesek, J.; Kennedy, J. D.; Thornton-Pett, M. J. Chem. Soc., Dalton Trans. 1995, 431.
108. Quintana, W.; Sneddon, L. G. Inorg. Chem. 1990, 29, 3242.
109. Ernest, R. L; Quintana, W.; Rosen, R.; Caroll, P. J.; Sneddon, L. G. Organometallics 1987, 6, 80.
110. (a) Green, T. A.; Switendick, A. C.; Emin, D. J. Chem. Phys. 1988, 89, 6815.
111. (b) Zahradník, R.; Balaji, V.; Michl, J. J. Comput. Chem. 1991, 12, 1147.
112. McKee, M. L. J. Am. Chem. Soc. 1997, 119, 4220.
113. McKee, M. L.; Bühl, M.; Charkin, O. P.; Schleyer, P. v. R. Inorg. Chem. 1993, 32, 4549.
114. Williams, R. E. Adv. Inorg. Chem. Radiochem. 1976, 18, 67.
115. Ott, J. J.; Gimarc, B. M. J. Am. Chem. Soc. 1986, 108, 4303.
116. (a) Jemmis, E. D. J. Am. Chem. Soc. 1982, 104, 7017.
117. (b) Jemmis, E. D.; Schleyer, P. v. R. J. Am. Chem. Soc. 1982, 104, 4781.
118. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
119. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.;. Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian94, Revision C.3; Gaussian Inc.: Pittsburgh, PA, 1995.
120. (b) Hehre, W.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
121. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502 and references therein.
122. (a) Reed, A. E.; Weinhold, F. Chem. Rev. 1988, 88, 899.
123. (b) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434.
124. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
125. (a) Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 194, 1.
126. (b) Bader, R. F. W.; Keith, T. A. J. Chem. Phys. 1993, 99, 3683.
127. (a) Plesek, J.; Jelínek, T.; Drdáková, E.; Hermánek, S.; Stíbr, B. Collect. Czech. Chem. Commun. 1984, 49, 1559.
128. (b) Plesek, J.; Jelínek, T.; Stíbr, B. Polyhedron 1984, 3, 1351.
129. (c) Maly, K.; Subrtová, V.; Petricek, V. Acta Crystallogr. 1987, C43, 593.
130. (d) Novák, C.; Subrtová, V.; Petricek, V.; Hummel, L.; Hasek, J. Collect. Czech. Chem. Commun. 1990, 55, 653.
131. (a) Jelínek, T.; Plesek, J.; Mares, F.; Hermánek, S.; Stíbr, B. Polyhedron. 1987, 6, 1981.
132. (b) Yakushev, A. B.; Sivaev, I. B.; Kuznetsov, I. Yu.; Butman, L. A.; Kuznetsov, N. T. Zh. Neorg. Khim. 1988, 33, 1398.
133. (c) Mair, F. S.; Morris, J. H.; Gaines, D. F.; Powell, D. J. Chem. Soc., Dalton Trans. 1993, 135.
134. Shelly, K.; Finster, D. C.; Lee, Y. J.; Scheidt, W. R.; Reed, C. A. J. Am. Chem. Soc. 1985, 107, 5955.
135. (a) Shelly, K.; Reed, C. A.; Lee, Y. J.; Scheidt, W. R. J. Am. Chem. Soc. 1986, 108, 3117.
136. (b) Gupta, G. P.; Lang, G.; Lee, Y. Ja.; Scheidt, W. R.; Shelly, K.; Reed, C. A. Inorg. Chem. 1987, 26, 3022.
137. Liston, D. J.; Reed, C. A.; Eigenbrot, C. W.; Scheidt, W. R. Inorg. Chem. 1987, 26, 2739.
138. Liston, D. J.; Lee, Y. J.; Scheidt, W. R.; Reed, C. A. J. Am. Chem. Soc. 1989, 111, 6643.
139. Hoffmann, R.; Lipscomb, W. N.J. Chem. Phys. 1962, 36, 3489.
140. Ivanov, S. V.; Lupinetti, A. J.; Miller, S. M.; Anderson, O. P.; Solntsev, K. A.; Strauss, S. H. Inorg. Chem. 1995, 34, 6419.
141. Jelinek, T.; Baldwin, P.; Scheidt, W. R.; Reed, C. A. Inorg. Chem. 1993, 32, 1982.
142. (a) Jelinek, T.; Plesek, J.; Hermanek, S.; Stíbr, B. Collect. Czech. Chem. Commun. 1986, 51, 819.
143. (b) Srivastava, R. R.; Hamlin, D. K.; Wilbur, D. S. J. Org. Chem. 1996, 61, 9041.
144. (a) Reed, C. A.; Xie, Z.; Bau, R.; Benesi, A. Science 1993, 262, 402.
145. (b) Xie, Z.; Jelinek, T.; Bau, R.; Reed, C. A. J. Am. Chem. Soc. 1994, 116, 1907.
146. (c) Xie, Z.; Bau, R.; Reed, C. A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2433.
147. (a) King, B. T.; Noll, B. C.; McKinley, A. J.; Michl, J. J. Am. Chem. Soc. 1996, 118, 10902 and reference therein.
148. (b) King, B. T.; Janousek, Z.; Grüner, B.; Trammell, M.; Noll, B. C.; Michl, J. J. Am. Chem. Soc. 1996, 118, 3313.
149. Nestor, K.; Stíbr, B.; Kennedy, J. D.; Thornton-Pett, M.; Jelínek, T. Collect. Czech. Chem. Commun. 1992, 57, 1262.
150. Xie, Z.; Liston, D. J.; Jelnik, T.; Mitro, V.; Bau, R.; Reed, C. A. J. Chem. Soc., Chem. Comun. 1993, 384.
151. Ivanov, S. V.; Rockwell, J. J.; Miller, S. M.; Andersen, O. P.; Solntsev, K. A.; Strauss, S. H. Inorg. Chem. 1996, 35, 7882.
152. (a) Klier, D. A.; Lipscomb. W. N. Inorg. Chem. 1979, 18, 1312.
153. (b) Muetterties, E. L.; Wiersama, R. J.; Hawthorne, M. F. J. Am. Chem. Soc. 1973, 95, 7520.
154. Aihara, J. J. Chem. Soc., Perkin Trans. 2 1996, 2185.
155. (a) Peck, R. C.; Schulman, J. M.; Disch, R. L. J. Phys. Chem. 1990, 94, 6637.
156. (b) Wiberg, K. B. J. Org. Chem. 1997, 62, 5720.
157. obs.
158. (a) Garratt, P. J. Aromaticity; Wiley: New York, 1986.
159. (b) Katritzky, A. R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc. 1989, 111, 7.
160. (c) Katritzky, A. R.; Feygelman, V.; Musumarra, G.; Barczynski, P.; Szafran, M. J. Prakt. Chem. /Chem. -Ztg. 1990, 332, 853.
161. (d) Jug, K.; Köster, A. M. J. Phys. Org. Chem. 1991, 4, 163.
162. (a) Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity; Wiley: New York, 1994.
163. (b) Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 68, 209.
164. (a) Dewar, M. J. S.; De Llano, C. J. Am. Chem. Soc. 1969, 91, 789.
165. (b) Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 305.
166. (c) Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750.
167. (d) Gutman, I.; Milun, M.; Trinajstic, N. J. Am. Chem. Soc. 1977, 99, 1692.
168. (a) Julg, A.; Francois, P. Theor. Chim. Acta 1967, 7, 249.
169. (b) Kruszewski, J.; Krygowski, T. M. Tetrahedron Lett. 1972, 3839.
170. (c) Herndon, W. C. J. Am. Chem. Soc. 1973, 95, 2404.
171. (d) Aihara, J. J. Org. Chem. 1976, 41, 2488.
172. (e) Jug, K. J. Org. Chem. 1983, 48, 1344.
173. (f) Bird, C. W. Tetrahedron 1985, 41, 1409.
174. Elvidge, J. A.; Jackman, L. M. J. Chem. Soc. 1961, 859.
175. (a) Fleischer, U.; Kutzelnigg, W.; Lazzeretti, P.; Mühlenkamp, V. J. Am. Chem. Soc. 1994, 116, 5298 and references therein.
176. (b) Benson, R. C.; Flygare, W. H. J. Am. Chem. Soc. 1970, 92, 7523.
177. (a) Dauben, H. J., Jr.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1968, 90, 811 and 1969, 91, 1991.
178. (a) Dauben, H. J., Jr.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1968, 90, 811 and 1969, 91, 1991.
179. (b) Benson, R. C.; Flygare, W. H. J. Am. Chem. Soc. 1970, 92, 7523.
180. (c) Dauben, H. J., Jr.; Wilson, J. D.; Laity, J. L. In Non-Benzenoid Aromatics; Snyder, J. P., Ed.; Academic Press: New York 1971 Vol 2, and references therein.
181. (d) Davidson, J. R.; Burnham, A. K.; Siegel, B.; Beak, P.; Flygare, W. H. J. Am. Chem. Soc. 1974, 96, 7394.
182. Schleyer, P. v. R.; Freeman, P.; Jiao, H.; Goldfuss, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 337.
183. Subramanian, G.; Schleyer, P. v. R.; Jiao, H. Angew. Chem., Int. Ed Engl. 1996, 35, 2638.
184. (a) Bühl, M.; Thiel, W.; Jiao, H.; Schleyer, P. v. R.; Saunders: M.; Anet, F. A. L. J. Am. Chem. Soc. 1994, 116, 7429 and references therein.
185. (b) Bühl, M.; van Wüllen, C. Chem. Phys. Lett. 1995, 247, 63.
186. h) is strongly endothermic, 170 kcal/mol, at B3LYP/6-31G*//B3LYP/ 6-31G*.
187. (a) Ditter, J. F.; Klusmann, E. B.; Williams, R. E.; Onak, T. Inorg. Chem. 1976, 15, 1063.
188. (b) Oh, B.; Onak, T. Inorg. Chem. 1982, 21, 3150.
189. (c) Siwapinyoyos, G.; Onak, T. Inorg. Chem. 1982, 21, 156.
190. (a) Olsen, R. R.; Grimes, R. N. J. Am. Chem. Soc. 1970, 92, 5072.
191. (b) Warren, R.; Paquin, D.; Onak, T.; Dunks, G.; Spielman, J. R. Inorg. Chem. 1970, 9, 2285.
192. (c) Beltram, G.; Fehlner, T. J. Am. Chem. Soc. 1979, 101, 6237.
193. (d) Takimoto, C.; Siwapinyoyos, G.; Fuller, K.; Fung, A. P.; Liauw, L.; Jarvis, W.; Millhauser, G.; Onak, T. Inorg. Chem. 1980, 19, 107.
194. (a) Ng, B.; Onak, T.; Banuelos, T.; Gomez, F.; DiStefano, E. W. Inorg. Chem. 1985, 24, 4091.
195. (b) Abdou, Z. J.; Soltis, M.; Oh, B.; Siwap, G.; Banuelos, T.; Nam, W.; Onak, T. Inorg. Chem. 1985, 24, 2363.
196. Nam, W.; Onak, T. Inorg. Chem. 1987, 26, 1581.
197. 12 (both experimental and computed, Table 2) are nearly the same.
198. (a) Subramanian, G.; Schleyer, P. v. R.; Jiao, H. Organometallics 1997, 16, 2362.
199. (b) Novak, I. J. Mol. Struct. (THEOCHEM) 1997, 398, 315.
200. Valkov, V. V.; Ikonsky, V. N. Izuest. Sub. Otdel. Akad. Nauk. Ser. Khim. Nauk. 1981, 6, 38.