Stability and three-dimensional aromaticity of closo-NBn-1Hn azaboranes, n = 5-12

Inorganic Chemistry

Volumn 42, Issue 13, 2003, Pages 4190-4203

  Najafian, Katayoun ^a   Schleyer, Paul von Rague ^b   Tidwell, Thomas T ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; AZABORANE DERIVATIVE; BORANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENERGY; ISOMER; MAGNETISM; MOLECULAR STABILITY; REACTION ANALYSIS;

EID: 0038577973     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0340783     Document Type: Article

References (121)

1. (a) Olah, G. A.; Wade, K.; Williams, R. E. Electron Deficient Boron and Carbon Clusters; John Wiley and Sons: New York, 1991.
2. (b) Olah, G. A.; Surya Prakash, G. K.; Williams, R. E.; Field, L. D.; Wade, K. Hypercarbon Chemistry; Wiley: New York, 1987.
3. (c) Wade, K. Electron Deficient Compounds; Nelson: London, 1971.
4. (a) Mingos, D. M. P.; Wales, D. J. Introduction to Cluster Chemistry; Prentice Hall: Englewood Cliffs, NJ, 1990.
5. (b) Minkin, V. I.; Minyaev, R. M.; Zhdanov, Yu. A. Nonclassical Structures of Organic Compounds; Mir Publishers: Moscow, 1987.
6. (a) King, R. B. Chem. Rev. 2001, 101, 1119.
7. (b) McKee, M. L.; Wang, Z.-X.; Schleyer, P. v. R. J. Am. Chem. Soc. 2000, 122, 4781.
8. (c) Schleyer, P. v. R.; Najafian, K.; Mebel, A. M. Inorg. Chem. 1998, 37, 6765.
9. (a) Muetterties, E. L. Boron Hydride Chmesitry; Academic Press: New York, 1975.
10. (b) Onak, T. Organoborane Chemistry; Academic Press: New York, 1975.
11. (c) Lipscomb, W. N. Boron Hydrides; W. A. Benjamin: New York, 1963.
12. (a) Casanova, J. The Borane, Carborane, Carbocation Continuum; Wiley: New York, 1998.
13. (b) 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.
14. (a) Williams, R. E. In Advances in Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1994.
15. (b) Liebman, J. F.; Greenberg A.; Williams, R. E. Advances in Boron and the Boranes; VCH Verlagsgesellschaft: New York, 1988.
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. (a) Schleyer, P. v. R.; Subramanian, G.; Jiao, H.; Najafian, K.; Hofmann, M. In Advances in Boron Chemistry; Sibert, W., Ed.; The Royal Society of Chemistry: Cambridge, England. 1997.
19. (b) Schleyer, P. v. R.; Subramanian, G.; Dransfeld, A. J. Am. Chem. Soc. 1996, 118, 9988.
20. (a) Schleyer, P. v. R.; Najafian, K. In The Borane, Carborane, Carbocation Continuum; Casanova, J., Ed.; Wiley: New York, 1998.
21. (b) Choi, C. H.; Kertesz, M. J. Chem. Phys. 1998, 108, 6681.
22. (c) Wannere, C. S.; Schleyer, P. v. R. Org. Lett., submitted.
23. Hofmann, M.; Fox, M. A.; Greatrex, R.; Schleyer, P. v. R.; Bausch, J. W.; Williams, R. E. Inorg. Chem. 1996, 35, 6170.
24. Vondrak, T.; Hermanek, S.; Plesek, J. Polyhedron 1993, 12, 1301.
25. (a) Little, J. C.; Moran, J. T.; Todd, L. J. J. Am. Chem. Soc. 1967, 89, 5495.
26. (b) Getman, T. D.; Deng, H.-B.; Hsu, L.-Y.; Shore, S. G. Inorg. Chem. 1989, 28, 3612.
27. Hynk, D.; Vajda, E.; Buhl, M.; Schleyer, P. v. R. Inorg. Chem. 1992, 31, 2464 and references therein.
28. Pretzer, W. R.; Rudlph, R. W. J. Am. Chem. Soc. 1973, 95, 931.
29. (a) Ivanov, S. V.; Lupinetti, A. J.; Miller, S. M.; Anderson, O. P.; Solntsev, K. A.; Strauss, S. H. Inorg. Chem. 1995, 34, 6419.
30. (b) Knoth, W. H. Little, J. L.; Lawrence, J. R.; Scholer, F. R.; Todd, L. J. Inorg. Synth. 1968, 11, 33.
31. (c) Knoth, W. H. J. Am. Chem. Soc. 1967, 89, 1274.
32. (a) Srivastava, R. R.; Hamlin, D. K.; Wilbur, D. S. J. Org. Chem. 1996, 61, 9041.
33. (b) Jelink, T.; Plesek, J.; Hermanek, S.; Stibr, B. Collect. Czech. Chem. Commun. 1986, 51, 819.
34. (c) Jelink, T.; Baldwin, P.; Scheidt, W. R.; Reed, C. A. Inorg. Chem. 1982, 1003, 32.
35. (a) Ivanov, S. V.; Rockwell, J. J.; Miller, S. M.; Anderson, O. P.; Solntsev, K. A.; Strauss, S. H. Inorg. Chem. 1996, 35, 7882.
36. (b) Xie, Z.; Liston, D. J.; Jelnik, T.; Mitro, V.; Bau, R.; reed, C. A. J. Chem. Soc., Chem. Commun. 1993, 384.
37. Wiersema, R. J.; Hawthorne, M. F. Inorg. Chem. 1973, 12, 785.
38. (a) Jelinek, T.; Stibr, B.; Plesek, J.; Kennedy, J. D.; Thornton-Pett. M. J. Chem. Soc., Dalton Trans. 1995, 431.
39. (b) Plesek, J.; Jelinek, T.; Stibr, B.; Hermanek, S. J. Chem. Soc., Chem. Commun. 1988, 384.
40. For example: (a) Gimarc, B. M.; Zaho, M. Inorg. Chem. 1996, 35, 825.
41. (b) Bregadze, V. I. Chem. Rev. 1992, 92, 209 and references therein.
42. (c) Plesek, J. Chem. Rev. 1992, 92, 269 and references therein.
43. (d) Gimarc, B. M.; Dai, B.; Ott, J. J. Comput. Chem. 1989, 10, 14.
44. For example: (a) Hynk, D.; Rankin, D. W. H.; Roberston, H. E.; Hofmann, M.; Schleyer, P. v. R.; Buhl, M. Inorg. Chem. 1994, 33, 4781.
45. (b) Schleyer, P. v. R.; Gauss, J.; Buhl, M.; Greatrex, R. A.; Fox, M. A. J. Chem. Soc., Chem. Commun. 1993, 23, 1766.
46. (c) Buhl, M.; Mebel, A. M.; Charkin, O.; Schleyer, P. v. R. Inorg. Chem. 1992, 31, 3769.
47. (d) Buhl, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1992, 114, 477.
48. (e) Buhl, M.; Gauss, J.; Hofmann, M.; Schleyer, P. v. R. Inorg. Chem. 1992, 31, 3769.
49. For example: (a) Xie, Z.; Jelinek, T.; Bau, R.; Reed, C. A. J. Am. Chem. Soc. 1994, 116, 1907.
50. (b) Xie, Z.; Bau, R.; Reed, C. A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2433.
51. (c) Reed, C. A.; Xie, Z.; Bau, R.; Benesi, A. Science 1993, 262, 402.
52. For example: (a) Ivanov, S. V.; Rockwell, J. J.; Miller, S. M.; Anderson, O. P.; Solnstev, K. A.; Strauss, S. H. Inorg. Chem. 1996, 35, 7882.
53. (b) Nestor, K.; Stibr, B.; Kennedy, J. D.; Thornton-Pett, M.; Jelinek, T. Collect. Czech. Chem. Commun. 1992, 57, 1262.
54. Arafat, A.; Baer, J.; Huffman, J. C.; Todd, L. J. Inorg. Chem. 1986, 25, 3757.
55. Muller, J.; Runsik, J.; Paetzold, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 175.
56. Hynk, D.; Buhl, M.; Schleyer, P. v. R.; Volden, H. V.; Gunderson, S.; Muller, J.; Paetzold, P. Inorg. Chem. 1993, 32, 2442.
57. Williams, R. E. Adv. Inorg. Chem. Radiochem. 1976, 18, 67.
58. Ott, J. J.; Gimarc, B. M. J. Am. Chem. Soc. 1986, 108, 4303.
59. Schleyer, P. v. R.; Najafian, K. Inorg. Chem. 1998, 37, 3454.
60. (a) Jemmis, E. D. J. Am. Chem. Soc. 1982, 104, 7017.
61. (b) Jemmis, E. D.; Schleyer, P. v. R. J. Am. Chem. Soc. 1982, 104, 4781.
62. Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 68, 209.
63. (a) Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1997, 119, 12669.
64. (b) Jiao, H.; Schleyer, P. v. R. Angew. Chem. Int. Ed. Engl. 1996, 35, 2383.
65. (c) Subramanian, G.; Schleyer, P. v. R.; Jiao, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2638.
66. (a) Subramanian, G.; Schleyer, P. v. R.; Jiao, H. Organometallics 1997, 16, 2362.
67. (b) Novak, I. J. Mol. Struct. (THEOCHEM) 1997, 398, 315.
68. Subramanian, G.; Schleyer, P. v. R.; Jiao, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2638.
69. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
70. (a) Dauben, H. P., Jr.; Wilson, J. D.; Laity, J. L. J. In Nonbenzenoid Aromatics; Snyder, J. P., Ed.: Academic Press: New York, 1971; Vol. 2, pp 167-206.
71. (b) Dauben, H. P., Jr.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1969, 91, 1991.
72. (c) Dauben, H. P., Jr.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1968, 90, 811.
73. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Faraks, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Oritz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
74. (b) See: The Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P. A., Schaefer, H. F., III, Schreiner, P. R., Eds.; John Wiley & Sons: Chichester, 1998.
75. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502 and references therein.
76. (a) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434.
77. (b) Reed, A. E.; Weinhold, F. Chem. Rev. 1988, 88, 899.
78. (a) Bader, R. F.; Keith, T. A. J. Chem. Phys. 1993, 99, 3683.
79. (b) Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 194, 1.
80. (a) Buhl, M.; Mebel, A. M.; Charkin, O. P.; Schleyer, P. v. R. Inorg. Chem. 1992, 31, 3769.
81. (b) Bausch, J. W.; Prakash, G. K. S.; Williams, R. E. Inorg. Chem. 1992, 31, 3763.
82. (c) Kleir, D. A.; Lipscomb, W. N. Inorg. Chem. 1979, 18, 1312.
83. (d) Muetterties, E. L.; Wiersama, R. J.; Hawthorne, M. F. J. Am. Chem. Soc. 1973, 95, 7520.
84. Schneider, L.; Englert, U.; Paetzold, P. Z. Anorg. Allg. Chem. 1994, 620, 1191.
85. Buhl, M.; Schleyer, P. v. R.; Havals, Z.; Hynk, D.; Hermanek, S. Inorg. Chem. 1991, 30, 3107.
86. Zahradnik, R.; Balaji, V.; Michl, J. J. Comput. Chem. 1991, 12, 1147.
87. Roth, W. R.; Hopf, H.; Wasser, T.; Zimmermann, H.; Werner, C. Liebigs Ann. 1996, 1691.
88. Aihara, J. J. Chem. Soc., Perkin Trans. 2 1996, 2185.
89. Peck, R. C.; Schulman, J. M.; Disch, R. L. J. Phys. Chem. 1990, 94, 6637.
90. Wiberg, K. B. J. Org. Chem. 1997, 62, 5720.
91. obs.
92. (a) Jug, K.; Koster, A. M. J. Phys. Org. Chem. 1991, 4, 163.
93. (b) Katritzky, A. R.; Feygelman, V.; Musumarra, G.; Barczynski, P.; Szafran, M. J. Prakt. Chem./Chem.-Ztg. 1990, 332, 835.
94. (c) Katritzky, A. R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc. 1989, 111, 7.
95. (d) Garret, P. J. Aromaticity; Wiley: New York, 1986.
96. (a) Krygowski, T. M.; Cyranski, M. K.; Czarnocki, Z.; Hafelinger, G.; Katritzky, A. R. Tetrahedron 2000, 56, 1783.
97. (b) Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 68, 209.
98. (c) Bird, C. W. Tetrahedron 1996, 52, 9945.
99. (d) Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity; Wiley: New York, 1994.
100. (a) Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 305.
101. (b) Dewar, M. J. S.; De Llano, C. J. Am. Chem. Soc. 1969, 91, 789.
102. (a) Gutman, I.; Milun, M.; Trinajstic, N. J. Am. Chem. Soc. 1977, 99, 1692.
103. (b) Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750.
104. Elvidge, J. A.; Jackman, L. M. J. Chem. Soc. 1961, 859.
105. (a) Fleischer, U.; Kutzelnigg, W.; Lazzeretti, P.; Muhlenkamp, V. J. Am. Chem. Soc. 1994, 116, 5296 and references therein.
106. (b) Benson, R. C.; Flygare, W. H. J. Am. Chem. Soc. 1970, 92, 7253.
107. (a) Herndon, W. C. J. Am. Chem. Soc. 1973, 95, 2404.
108. (b) Kruszewski, J.; Krygowski, T. M. Tetrahedron Lett. 1972, 3839.
109. (c) Jug, A.; Francois, P. Theor. Chim. Acta 1967, 7, 249.
110. (a) Bird, C. W. Tetrahedron 1985, 41, 1409.
111. (b) Jug, K. J. Org. Chem. 1983, 48, 1344.
112. (c) Aihara, J. J. Org. Chem. 1976, 41, 2488.
113. (a) Patchkovskii, S.; Thiel, W. J. Mol. Model. 2000, 6, 67 and references cited.
114. (b) Sawicka, D.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 864.
115. (c) Buhl, M. Chem. Eur. J. 1998, 4, 734.
116. (a) Lera, A. R.; Alvarez, R.; Lecea, B.; Torrado, A.; Cossio, F. P. Angew. Chem., Int. Ed. 2001, 40, 557.
117. (b) Verevkin, S. P.; Beckhaus, H.-D.; Ruckhardt, C.; Haag, R.; Kozhushkov, S. I.; Zywietz, T.; de Meijere, A.; Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1998, 120, 11130.
118. (a) Nyulaszi, L.; Schleyer, P. v. R. J. Am. Chem. Soc. 1999, 121, 6872.
119. (b) Chesnut, D. B. Chem. Phys. 1998, 231, 1.
120. (a) Krygowski, T. M.; Cyranski, M. K. Chem. Rev. 2001, 101, 1385.
121. (b) Abraham, R. J.; Canton, M.; Reid, M.; Griffiths, L. J. Chem. Soc., Perkin Trans. 2 2000, 803.