Gas-phase synthesis, submillimeter spectra, and precise structure of monomeric, solvent-free CuCH3

Journal of the American Chemical Society

Volumn 126, Issue 39, 2004, Pages 12621-12627

  Grotjahn, Douglas B ^a   Halfen, DeWayne T ^b   Ziurys, Lucy M ^b   Cooksy, Andrew L ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

^b University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CHEMICAL BONDS; DERIVATIVES; METHANE; MILLIMETER WAVES; MONOMERS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

COORDINATED SOLVENTS; GAS-PHASE SYNTHESIS; MILLIMETER-WAVE ROTATIONAL SPECTROSCOPY; ORGANOCOPPER;

COPPER;

CARBON; CARBON 13; COPPER 63; COPPER 65; COPPER DERIVATIVE; ISOTOPE; METHANE; METHYL GROUP; METHYLCOPPER; MONOMER; ORGANOMETALLIC COMPOUND; SILANE DERIVATIVE; SOLVENT; TETRAMETHYLSILANE; UNCLASSIFIED DRUG;

ARTICLE; BOND ANGLE; BOND LENGTH; CHEMICAL BOND; CHEMICAL STRUCTURE; DISTORTION CONSTANT; GAS; GAS PHASE SYNTHESIS; GEOMETRY; ISOTOPE LABELING; MEASUREMENT; MILLIMETER WAVE ROTATIONAL SPECTROSCOPY; ORGANIC CHEMISTRY; ROTATIONAL CONSTANT; SPECTROSCOPY; SYNTHESIS; VAPOR;

EID: 4644341044     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0490166     Document Type: Article

References (106)

1. Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-632.
2. Organocopper reagents: a practical approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford and New York, 1994.
3. Modern organocopper chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
4. Lipshutz, B. H. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; Wiley: Chichester, UK, and New York, 2002; pp 665-815.
5. Kharasch, M. S.; Tawney, P. O. J. Am. Chem. Soc. 1941, 63, 2308-2315.
6. House, H. O.; Respess, W. L.; Whitesides, G. M. J. Org. Chem. 1966, 31, 3128-3141.
7. Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978-4979.
8. Malkov, A. V.; Pernazza, D.; Bell, M.; Bella, M.; Massa, A.; Teply, F.; Meghani, P.; Kocovsky, P. J. Org. Chem. 2003, 68, 4727-4742.
9. Diaz-Requejo, M. M.; Caballero, A.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. J. Am. Chem. Soc. 2002, 124, 978-983.
10. Dambacher, J.; Bergdahl, M. Org. Lett. 2003, 5, 3539-3541.
11. Buckton, G. B. Ann. Chem. Pharm. 1859, 109, 218-227.
12. Reich, M. R. C. R. Hebd. Seances Acad. Sci. 1923, 177, 322-324.
13. Gilman, H.; Jones, R. G.; Woods, L. A. J. Org. Chem. 1952, 17, 1630-1634.
14. Costa, G.; DeAlti, G. Gazz. Chim. Ital. 1957, 87, 1273-1280.
15. Costa, G.; De Alti, G.; Stefani, L.; Boscarato, G. Ann. Chim. 1962, 52, 289-304.
16. Thiele, K. H.; Koehler, J. J. Organomet. Chem. 1968, 12, 225-229.
17. Ikariya, T.; Yamamoto, A. J. Organomet. Chem. 1974, 72, 145-151.
18. Bähr, G.; Burba, G. In Methoden der Organishen Chemie (Houben-Weyl); Müller, E., Ed.; Thieme: Stuttgart, 1970; Vol. 13/1, pp 731-761.
19. Costa, G.; Pellizer, G.; Rubessa, F. J. Inorg. Nucl. Chem. 1964, 26, 961-964.
20. Miyashita, A.; Yamamoto, A. Bull. Soc. Chem. Jpn. 1977, 50, 1102-1108.
21. Miyashita, A.; Yamamoto, T.; Yamamoto, A. Bull. Soc. Chem. Jpn. 1977, 50, 1109-1117.
22. Coan, P. S.; Folting, K.; Huffman, J. C.; Caulton, K. G. Organometallics 1989, 8, 2724-2728.
23. Lang, H.; Köhler, K.; Blau, S. Coord. Chem. Rev. 1995, 143, 113-168.
24. Janssen, M. D.; Köhler, K.; Herres, M.; Dedieu, A.; Smeets, W. J. J.; Spek, A. L.; Grove, D. M.; Lang, H.; van Koten, G. J. Am. Chem. Soc. 1996, 118, 4817-4829.
25. Stein, T.; Lang, H. J. Organomet. Chem. 2002, 664, 142-149.
26. Parnis, J. M.; Mitchell, S. A.; Garcia-Prieto, J.; Ozin, G. A. J. Am. Chem. Soc. 1985, 107, 8169-8178.
27. van Koten, G.; James, S. L.; Jastrzebski, J. T. B. H. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 3, pp 57-133.
28. Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 11.
29. Schade, C.; Schleyer, P. v. R. Adv. Organomet. Chem. 1987, 27, 159-278.
30. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem 1985, 24, 43-120.
31. Power, P. P. Prog. Inorg. Chem. 1991, 39, 75-112.
32. Nobel, D.; Van Koten, G.; Spek, A. L. Angew. Chem., Int. Ed. Engl. 1989, 28, 208-210.
33. Lingnau, R.; Strähle, J. Angew. Chem., Int. Ed. Engl. 1988, 27, 436.
34. Bertz, S. H.; Dabbagh, G.; He, X.; Power, P. P. J. Am. Chem. Soc. 1993, 115, 11640-11641.
35. Eriksson, H.; Hakansson, M. Organometallics 1997, 16, 4243-4244.
36. Dempsey, D. F.; Girolami, G. S. Organometallics 1988, 7, 1208-1213.
37. Leoni, P.; Pasquali, M.; Ghilardi, C. A. J. Chem. Soc., Chem. Commun. 1983, 240-241.
38. Poirier, R. A.; Ozin, G. A.; McIntosh, D. F.; Csizmadia, I. G.; Daudel, R. Chem. Phys. Lett. 1983, 101, 221-228.
39. Ziegler, T.; Tschinke, V.; Becke, A. J. Am. Chem. Soc. 1987, 109, 1351-1358.
40. Bauschlicher, C. W., Jr.; Langhoff, S. R.; Partridge, H.; Barnes, L. A. J. Chem. Phys. 1989, 91, 2399-2411.
41. Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1989, 111, 6524-6536.
42. Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1989, 111, 4635-4643.
43. Nakamura, E.; Nakamura, M.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 99-106.
44. Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Chem. Soc., Faraday Trans. 1994, 1789-1798.
45. Mori, S.; Nakamura, E. J. Mol. Struct. (THEOCHEM) 1999, 461-462, 167-175.
46. Sodupe, M.; Bauschlicher, C. W.; Lee, T. J. Chem. Phys. Lett. 1992, 189, 266-272.
47. Sosa, C.; Andzelm, J.; Elkin, B. C.; Wimmer, E.; Dobbs, K. D.; Dixon, D. A. J. Phys. Chem. 1992, 96, 6630-6636.
48. Böhme, M.; Frenking, G.; Reetz, M. T. Organometallics 1994, 13, 4237-4245.
49. Antes, I.; Frenking, G. Organometallics 1995, 14, 4263-4268.
50. Snyder, J. P.; Bertz, S. H. J. Org. Chem. 1995, 60, 4312-4313.
51. Barone, V.; Adamo, C. J. Phys. Chem. 1996, 100, 2094-2099.
52. Hermann, H. L.; Boche, G.; Schwerdtfeger, P. Chem. Eur. J. 2001, 7, 5333-5342.
53. Suresh, C. H.; Koga, N. J. Am. Chem. Soc. 2002, 124, 1790-1797.
54. Hope, H.; Olmstead, M. M.; Power, P. P.; Sandell, J.; Xu, X. J. Am. Chem. Soc. 1985, 107, 4337-4339.
55. Martin, S. F.; Fishpaugh, J. R.; Power, J. M.; Giolando, D. M.; Jones, R. A.; Nunn, C. M.; Cowley, A. H. J. Am. Chem. Soc. 1988, 110, 7226-7228.
56. John, M.; Auel, C.; Behrens, C.; Marsch, M.; Harms, K.; Bosold, F.; Gschwind, R. M.; Rajamohanan, P. R.; Boche, G. Chem. Eur. J. 2000, 6, 3060-3068.
57. Ziurys, L. M.; Barclay, W. L., Jr.; Anderson, M. A.; Fletcher, D. A.; Larnb, J. W. Rev. Sci. Instrum. 1994, 65, 1517-1522.
58. Bawn, C. E. H.; Whitby, F. J. J. Chem. Soc. 1960, 3926-3931.
59. Grotjahn, D. B.; Pesch, T. C.; Brewster, M. A.; Ziurys, L. M. J. Am. Chem. Soc. 2000, 122, 4735-4741.
60. Grotjahn, D. B.; Pesch, T.; Xin, J.; Ziurys, L. M. J. Am. Chem. Soc. 1997, 119, 12368-12369.
61. Ebert, G.; Rieke, R. D. J. Org. Chem. 1984, 49, 5280-5282.
62. Biedermann, S.; Bürger, H.; Hassler, K.; Höfler, F. Monatsh. Chem. 1980, 111, 703-714.
63. Saljoughian, M. Monatsh. Chem. 1984, 115, 519-521.
64. Bruno, J. W.; Smith, G. M.; Marks, T. J.; Fair, C. K.; Schultz, A. J.; Williams, J. M. J. Am. Chem. Soc. 1986, 108, 40-56.
65. O'Hair, R. A.; Bowie, J. H.; Currie, G. J. Aust. J. Chem. 1988, 41, 57-67.
66. Kawa, H.; Manley, B. C.; Lagow, R. C. Polyhedron 1988, 7, 2023-2025.
67. Ajjou, J. A. N.; Rice, G. L.; Scott, S. L. J. Am. Chem. Soc. 1998, 120, 13436-13443.
68. Visser, C.; Meetsma, A.; Hessen, B. Organometallics 2002, 21, 1912-1918.
69. Allerhand, A.; Dohrenwend, M. J. Am. Chem. Soc. 1985, 107, 6684-6688.
70. Townes, C. H.; Schawlow, A. L. Microwave Spectroscopy; Dover: New York, 1975.
71. Gordy, W.; Cook, R. L. Microwave Molecular Spectra; Wiley: New York, 1984.
72. Pickett, H. M. J. Mol. Spectrosc. 1991, 148, 371-377.
73. -1 more energy than the bend, causing the two K manifolds to become similar in energy and perturbations between them likely to become observable.
74. Kisiel, Z. J. Mol. Spectrosc. 2003, 218, 58-67.
75. Watson, J. K. G.; Roytburg, A.; Ulrich, W. J. Mol. Spectrosc. 1999, 196, 102-119.
76. 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.; Q. 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.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
77. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. J.; 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, 1347-1363.
78. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968-5975.
79. Brewster, M. A.; Ziurys, L. M. J. Chem. Phys. 2002, 117, 4853-4860.
80. Sheridan, P. M.; Ziurys, L. M. J. Chem. Phys. 2003, 118, 6370-6379.
81. Grotjahn, D. B.; Brewster, M. A.; Ziurys, L. M. J. Am. Chem. Soc. 2002, 5895-5901.
82. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
83. Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033-1036.
84. Hay, P. J. J. Chem. Phys. 1977, 66, 4377-4384.
85. Raghavachari, K.; Trucks, G. W. J. Chem. Phys. 1989, 91, 1062-1065.
86. Cooksy, A. L.; Tao, F.-M.; Klemperer, W.; Thaddeus, P. J. Phys. Chem. 1995, 99, 11095-11095.
87. Parker, C. L.; Cooksy, A. L. J. Phys. Chem. A 1999, 103, 2160-2169.
88. Sattelmeyer, K., personal communication, 2004.
89. Pou-Amerigo, R.; Merchan, M.; Nebot-Gil, I.; Widmark, P. O.; Roos, B. O. Theor. Chim. Acta 1995, 92, 149-182.
90. Werner, H.-J. Adv. Chem. Phys. 1987, 69, 1-62.
91. Townes, C. H.; Schawlow, A. L. Microwave Spectroscopy; Dover: New York, 1975.
92. Gholami, M. R.; Wight, R.; Xu, D.; Cooksy, A. L., in preparation.
93. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry; John Wiley and Sons: New York, 1997.
94. Wiberg, K.; Breneman, C. M. J. Am. Chem. Soc. 1990, 112, 8765-8775.
95. Experimental data for other metal-methyl species have been reported, but in these cases the C-H bond lengths and H-C-H angles were assigned typical values (rather than experimentally determined ones) so that the metal-carbon bond length could be calculated. See: Cerny, T. M.; Tan, X. Q.; Williamson, J. M.; Robles, E. S. J.; Ellis, A. M.; Miller, T. A. J. Chem. Phys. 1993, 99, 9376-9388.
96. Robinson, J. S.; Ziurys, L. M. Astrophys. J. 1996, 472, L131-L134.
97. Anderson, M. A.; Ziurys, L. M. Astrophys. J. (Lett.) 1995, 452, L157-L160.
98. Anderson, M. A.; Robinson, J. S.; Ziurys, L. M. Chem. Phys. Lett. 1996, 257, 471-480.
99. Xin, J.; Robinson, J. S.; Apponi, A.; Ziurys, L. M. J. Chem. Phys. 1998, 108, 2703-2711.
100. Bent, H. A. Chem. Rev. 1961, 61, 275-311.
101. He, X.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 1992, 114, 9668-9670.
102. Anderson, M. A.; Ziurys, L. M. Astrophys. J. (Lett.) 1996, 460, L77.
103. Anderson, M. A.; Ziurys, L. M. Astrophys. J. (Lett.) 1995, 452, L157.
104. Duncan, J. L. J. Mol. Struct. 1970, 6, 447-456.
105. Eggers, D. F., Jr. J. Mol. Struct. 1976, 31, 367-370.
106. Demaison, J.; Breidung, J.; Thiel, W.; Papousek, D. Struct. Chem. 1999, 10, 129-133.