Metal cation-methyl interactions in CB11Me12 - salts of Me3Ge+, Me3Sn +, and Me3Pb+

Journal of the American Chemical Society

Volumn 126, Issue 38, 2004, Pages 12033-12046

  Zharov, Ilya ^a,b   Weng, Tsu Chien ^c   Orendt, Anita M ^b   Barich, Dewey H ^b   Penner Hahn, James ^c   Grant, David M ^b   Havlas, Zdenek ^d   Michl, Josef ^a  

^a UNIVERSITY OF COLORADO   (United States)

^b UNIVERSITY OF UTAH   (United States)

^c UNIVERSITY OF MICHIGAN   (United States)

^d INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSTATICS; GERMANIUM; ISOMERS; LEAD; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PROBABILITY DENSITY FUNCTION;

ALKANE SOLVENTS; BORON ATOMS; ELECTROSTATIC POTENTIAL;

POSITIVE IONS;

BORON DERIVATIVE; CARBON; CATION; COORDINATION COMPOUND; GERMANIUM DERIVATIVE; LEAD; METAL DERIVATIVE; METHYL GROUP; TIN DERIVATIVE;

ANION TRANSPORT; ARTICLE; ATOMIC EMISSION SPECTROMETRY; CALCULATION; CATION TRANSPORT; CHEMICAL BINDING; CHEMICAL INTERACTION; COVALENT BOND; DENSITY FUNCTIONAL THEORY; ELECTRIC POTENTIAL; ION TRANSPORT; ISOMER; MASS SPECTROMETRY; METAL BINDING; NUCLEAR MAGNETIC RESONANCE; SURFACE CHARGE; SURFACE PROPERTY;

BORON COMPOUNDS; CATIONS; ELECTROSTATICS; FOURIER ANALYSIS; GERMANIUM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; SPECTRUM ANALYSIS; TETRAETHYL LEAD; TRIMETHYLTIN COMPOUNDS;

EID: 4644298922     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0475205     Document Type: Article

References (96)

1. Hall, C.; Perutz, R. N. Chem. Rev. 1996, 96, 3125 and references therein.
2. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879 and references therein.
3. Marks, T. J.; Chen, E. Y.-X. Chem. Rev. 2000, 100, 1391 and references therein.
4. Burns, C. J.; Andersen, R. A. J. Am. Chem. Soc. 1987, 109, 5853.
5. Stults, S. D.; Andersen, R. A.; Zalkin, A. J. Am. Chem. Soc. 1989, 111, 4507.
6. Berg, D. J.; Andersen, R. A. Organometallics 2003, 22, 627.
7. Zhang, S.; Piers, W. E. Organometallics 2001, 20, 2088.
8. Ingelson, M. J.; Mahon, M. F.; Patmore, N. J.; Ruggiero, G. D.; Weller, A. S. Angew. Chem., Int. Ed. 2002, 41, 3694.
9. Clarke, A. J.; Ingleson, M. J.; Kociok-Köhn, G.; Mahon, M. F.; Patmore, N. J.; Rourke, J. P.; Ruggiero, G. D.; Weller, A. S. J. Am. Chem. Soc. 2004, 126, 1503.
10. Zharov, I.; King, B. T.; Havlas, Z.; Pardi, A.; Michl, J. J. Am. Chem. Soc. 2000, 122, 10253.
11. Lickis, P. D. In The Chemistry of Organic Silicon Compounds, 2nd ed.; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: Chichester, UK, 1998; pp 557-594.
12. Reed, C. A. Acc. Chem. Res. 1998, 31, 325.
13. Zharov, I.; Michl, J. In The Chemistry of Organic Germanium, Tin and Lead Compounds; Rappoport, Z., Apeloig, Y., Eds,; Wiley & Sons: Chichester, 2002; Vol. 2, p 633.
14. Ashradi, M.; Johnels, D.; Edlund, U. Chem. Commun. 1996, 1279.
15. Arshadi, M.; Johnels, D.; Edlund, U.; Ottosson, C-H.; Cremer, D. J. Am. Chem. Soc. 1996, 118. 5120.
16. Schleyer, P. v. R.; Buzek, P.; Müller, T.; Apeloig, Y.; Siehl, H.-U. Angew. Chem., Int. Ed. Engl 1993, 32, 1471.
17. Olah, G. A.; Rasul, G.; Prakash, G. K. S. J. Organomet. Chem. 1996, 521, 271.
18. (a) Lambert, J. B.; Zhang, S.; Stem, C. L.; Huffman, J. C. Science 1993, 260, 1917.
19. (b) Lambert, J. B.; Zhang, S.; Ciro, S. M. Organometallics 1994, 13, 2430.
20. (a) Lupinetti, A. J.; Strauss, S. H. Chemtracts 1998, 11, 565.
21. (b) Reed, C. A. Acc. Chem. Res. 1998, 31, 133.
22. (c) Krossing, I.; Raabe, I. Angew. Chem., Int. Ed. 2004, 43, 2066.
23. Xie, Z.; Bau, R.; Benesi, A.; Reed, C. A. Organometallics 1995, 14, 3933.
24. Lambert, J. B.; Zhao, Y. Angew. Chem., Int. Ed. Engl 1997, 36, 400.
25. Kim, K.-C.; Reed, C. A.; Elliott, D. W.; Mueller, L. J.; Tham, F.; Lin, L.; Lambert, J. B. Science 2002, 297, 825.
26. Lambert, J. B.; Lin, L.; Keinan, S.; Muller, T. J. Am. Chem. Soc. 2003, 125, 6022.
27. Sekiguchi, A.; Fukawa, T.; Lee, V. Y.; Nakamoto, M. J. Am. Chem. Soc. 2003, 125, 9250.
28. Sekiguchi, A.; Fukawa, T.; Lee, V. Y.; Nakamoto, M.; Ichinohe, M. Angew. Chem., Int. Ed. 2003, 42, 1143.
29. Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M. Science 1997, 275, 60.
30. Sekiguchi, A.; Matsuno, T.; Ichinohe, M. J. Am. Chem. Soc. 2000, 122, 11250.
31. Sekiguchi, A.; Fukaya, N.; Ichinohe, M.; Ishida, Y. Eur. J. Inorg. Chem. 2000, 6, 1155.
32. Sekiguchi, A.; Ichinohe, M.; Nakamoto, M. Organometallic News 2003, 1, 11.
33. Grimes, R. N. Carboranes; Academic Press: New York & London, 1970.
34. (a) Knoth, W. H. J. Am. Chem. Soc. 1967, 89, 1274.
35. (b) Knoth, W. H. Inorg. Chem. 1971, 10, 598.
36. Franken, A.; King, B. T.; Rudolph, J.; Rao, P.; Noll, B. C.; Michl, J. Collect. Czech. Chem. Commun. 2001, 66, 1238.
37. Wiersema, R. J.; Hawthorne, M. F. Inorg. Chem. 1973, 12, 785.
38. (a) Jelínek, T.; Plešek, J.; Heřmánek, S.; Stíbr, B. Collect. Czech. Chem. Commun. 1986, 51, 819.
39. (b) Plešek, J.; Plešk, Z.; Stuchlík, J.; Heřmánek, S. Collect. Czech. Chem. Commun. 1981, 46, 1748.
40. (a) Plešek, J. Chem. Rev. 1992, 92, 269.
41. (b) Strauss, S. H. In Contemporary Boron Chemistry; Wade, K., Marder, T. B., Hughes, A., Eds.; Royal Society of Chemistry: London, 2000; Vol. 253, p 44.
42. (c) Stasko, D.; Reed, C. A. J. Am. Chem. Soc. 2002, 124, 1148.
43. King B. T.; Janoušek, Z.; Grüner, B.; Trammell, M.; Noll, B. C.; Michl, J. J. Am. Chem. Soc. 1996, 118, 3313.
44. Clayton, J. R.; King, B. T.; Zharov, I.; Michl, J. Submitted for publication.
45. King, B. T.; Michl, J. J. Am. Chem. Soc. 2000, 122, 10255.
46. King, B. T.; Noll, B. C.; McKinley, A. J.; Michl, J. J. Am. Chem. Soc. 1996, 118, 10902.
47. Pospíšil, L.; King, B. T.; Michl, J. Electrochim. Acta 1998, 44, 103.
48. Corey, J. Y. J. Am. Chem. Soc. 1975, 97, 3237.
49. Xie, Z.; Manning, J.; Reed, R. W.; Mathur, R.; Boyd, P. D.; Benesi, A.; Reed, C. A. J. Am. Chem. Soc. 1996, 118, 2922.
50. Lambert, J. B.; Zhao, Y.; Wu, H.; Tse, W. C.; Kuhlman. B. J. Am, Chem. Soc. 1999, 121, 5001.
51. Ichinohe, M.; Fukui, H.; Sekiguchi, A. Chem. Lett. 2000, 12, 600.
52. Fukuzumi, S.; Kitano, T.; Mochida, K. J. Am. Chem. Soc. 1990, 112, 3246.
53. Loczynski, S.; Boduszek, B.; Shine, H. J. J. Org. Chem. 1991, 56, 914.
54. Doretti, L.; Faleschini, S. Gazz. Chim. Ital. 1970, 100, 819.
55. Kochi, J. K. Angew. Chem., Int. Ed. Engl. 1988, 27, 1227.
56. Zharov, I.; Fete, M. G.; Michl, J. Unpublished results.
57. Dakternieks, D.; Lim, A. E. K.; Lim, K. F. Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 150-151, 339.
58. (b) Henderson, W.; Taylor, M. J. Polyhedron 1996, 15, 1957.
59. Bullpitt, M.; Kitching, W.; Adcock, W. J. Organomet. Chem. 1976, 116, 161.
60. Kira, M.; Oyamada, T.; Sakurai, H. J. Organomet. Chem. 1994, 471, C4.
61. Lamben, J. B.; Kuhlmann, B. J. Chem. Soc., Chem. Commun. 1992, 931.
62. Birchall, T.; Manivannan, V. J. Chem. Soc., Dalton Trans. 1985, 2671.
63. Blackweil, J. M.; Piers, W. E.; McDonald R. J. Am. Chem. Soc. 2002, 124, 1295.
64. Henderson, L. D.; Piers, W. E.; Irvine, G. J.; McDonald, R. Organometallics 2002, 21, 340.
65. Lambert, J. B.; Ciro, S. M.; Stern, C. L. J. Organomet. Chem. 1995, 499, 49.
66. 13C NMR Data for Organometallic Compounds; Academic Press: London, 1981; pp 64-77.
67. Neumann, W. P.; Kuehlein, K. Justus Liebigs Ann. Chem. 1967, 702, 13.
68. Harris, R. K. In NMR and Periodic Table; Harris, R. K., Mann, B. E., Eds.; Academic Press: London, 1978; p 7.
69. Arnold, D. P.; Wells, P. R. J. Organomet. Chem. 1976, 111, 269.
70. Gilman, H.; Jones, R. G. J. Am. Chem. Soc. 1950, 72, 1760.
71. Wrackmeyer, B.; Horchler, K. In Annual Reports on NMR Spectroscopv; Webb, G. A., Ed.; Academic Press: London, 1990; Vol. 22, pp 249-250.
72. Sebald, A. In Advanced Applications of NMR to Organometallic Chemistry; Gielen, M., Willem, R., Wrackmeyer, B., Eds.; Wiley & Sons: Chichester. UK, 1996; pp 124-157.
73. Performed by Prof. Peter W. Stephens at the State University of New York, Stony Brook, NY.
74. (a) Chieh, P. C. J. Chem. Soc. A 1971, 3243.
75. (b) Belsky, V. K.; Simonenko, A. A.; Reikhsfeld, V. O.; Saratov, I. E. J. Organomet. Chem. 1983, 244, 125.
76. (c) Preut, H.; Huber, F. Acta Crystallogr. C 1993, 49, 1373.
77. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin. Trans 2 1987, S1.
78. Riggs-Gelasco, P. J.; Mei, R.; Ghanotakis, D. F.; Yocum, C. F.; Penner-Hahn, J. E. J. Am. Chem. Soc. 1996, 118, 2400.
79. Bondi, A. J. Phys. Chem. 1964, 68, 441.
80. Davies, A. G. Organotin Chemistry; VCH: Weinheim, 1997.
81. Batsanov, S. S. Russ. J. Gen. Chem. 1998, 68, 495.
82. Zharov, I. Ph.D. Dissertation, University of Colorado at Boulder, 2000; p 53
83. King, B. T.; Noll, B. C.; Michl, J. Collect. Czech. Chem. Commun. 1999, 64, 1001.
84. Crowther, D. J.; Borkowsky, S. J.; Swenson, D.; Meyer, T. Y.; Jordan, R. F. Organometallics 1993, 12, 2897, and references therein.
85. NBO, Version 3.1: Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
86. (a) Zahradník, R.; Balaji, V.; Michl, J. J. Comput. Chem. 1991, 12, 1147.
87. (b) McKee, M. L. J. Am. Chem. Soc. 1997, 119, 4220.
88. Harris, R. K.; Sebald, A. Magn. Reson. Chem. 1987, 25, 1058.
89. Brown, I. D.; Altermatt, D. Acta Crystallogr. 1985, B41, 244.
90. 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.; Farkas, 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.; Ortiz, 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
91. Schaftenaar, G.; Noordik, J. M. J. Comput.-Aided Mol. Design 2000, 14, 123.
92. H, B, C: Dunnins Jr., T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer. H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, pp 1-28. Ge. Sn, Pb: Igel-Mann, G.; Stoll, H.; Preuss, H. Mol. Phys. 1988, 65, 1321.
93. H, B, C: Dunnins Jr., T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer. H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, pp 1-28. Ge. Sn, Pb: Igel-Mann, G.; Stoll, H.; Preuss, H. Mol. Phys. 1988, 65, 1321.
94. H, C: Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. B: Dill, J. D.; Pople, J. A. J. Chem. Phys. 1975, 62, 2921.
95. +: Clark, T.; Chandrasekhar, J.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
96. d: Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.