A Calix[4]arene Carceplex with Four Rh24+ Fasteners

Journal of the American Chemical Society

Volumn 126, Issue 5, 2004, Pages 1518-1525

  Cotton, F Albert ^a   Lei, Peng ^a   Lin, Chun ^a   Murillo, Carlos A ^a   Wang, Xiaoping ^a   Yu, Shu Yan ^a,b   Zhang, Zhong Xing ^b  

^a TEXAS A AND M UNIVERSITY   (United States)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; CARBOXYLIC ACIDS; CRYSTAL ORIENTATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

CARCEPLEX STRUCTURE; DISTILLED WATER;

RHODIUM COMPOUNDS;

25,26,27,28 TETRA N PROPOXYCALIX[4]ARENE 5,11,17,23 TETRACARBOXYLIC ACID; ACETONITRILE; CALIXARENE; CARBOXYLIC ACID DERIVATIVE; CATION; ETHER; MOLYBDENUM; RHODIUM; TETRYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CRYSTALLIZATION; INFRARED RADIATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 1042288170     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0396899     Document Type: Article

References (96)

1. (a) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853 and references therein.
2. (b) Swiegers, G. F.; Malefetse. T. J. Chem. Rev. 2000, 100, 3483.
3. (c) Espinet, P.; Soulantica, K.; Charmant, J. P. H.; Orpen, A. G. Chem. Commun. 2000, 915.
4. (d) Navarro, J. A. R.; Lippert, B. Coord. Chem. Rev. 1999, 185/186, 653.
5. (e) Whang, D.; Kim, K. J. Am. Chem. Soc. 1997, 119, 451.
6. (f) Mann, S.; Huttner, G.; Zsolnai, L.; Heinze, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2808.
7. (g) Scherer, M.; Caulder, D. L.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 1999, 38, 1588.
8. (h) Lai, S.-W.; Chan, M. C.-W.; Peng, S.-M.; Che, C.-M. Angew. Chem., Int. Ed. 1999, 38, 669.
9. (i) Jones, C. J. Chem. Soc. Rev. 1998, 27, 289.
10. (j) Klausmeyer, K. K.; Wilson, S. R.; Rauchfuss, T. B. J. Am. Chem. Soc. 1999, 121, 2705.
11. (k) Li, H.; Eddaoudi, M.; O'Keeffe, M.; Yaghi, O.-M. Nature 1999, 402, 276.
12. Cotton, F. A.; Lin, C.; Murillo, C. A. Proc. Nat. Acad. Sci. U.S.A. 2002, 99, 4810.
13. Angaridis, P.; Berry, J. F.; Cotton, F. A.; Murillo, C. A.; Wang, X. J. Am. Chem. Soc. 2003, 125, 10327.
14. Cotton, F. A.; Lin, C.; Murillo, C. A. Acc. Chem. Res. 2001, 34, 759.
15. See, for example: (a) Doyle, M. P.; Ren, T. Prog. Inorg. Chem. 2001, 49, 113.
16. (b) Estevan, F.; Herbst, K.; Lahuerta, P.; Barberis, M.; Pérez-Prieto, J. Organometallics 2001, 20, 950.
17. (c) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366.
18. (d) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds - From Cyclopropanes to Ylides; John Wiley & Sons: New York, 1998.
19. (a) Seidel, S. R.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972.
20. (b) Fujita, M. Chem. Soc. Rev. 1998, 27, 417.
21. (c) Yu, S.-Y.; Kusukawa, T.; Biradha, K.; Fujita, M. J. Am. Chem. Soc. 2000, 122, 2665.
22. (d) Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 1397.
23. (e) Terpin, A. J.; Ziekler, M.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 2001, 40, 157.
24. (f) Fujita, M.; Nagao, S.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 1649.
25. (g) O'Leary, B. M.; Szabo, T.; Svenstrup, N.; Schalley, C. A.; Lützen, A.; Schäfer, M.; Rebek, J., Jr. J. Am. Chem. Soc. 2001, 123, 11519.
26. (h) Shivanyuk, A.; Rebek, J., Jr. J. Am. Chem. Soc. 2002, 124, 12074.
27. (i) Reek, J. N. H.; Schenning, A. P. H. J.; Bosman, A. W.; Meijer, E. W. ; Crossley, M. J. Chem. Commun. 1998, 11.
28. (a) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, 1994.
29. (b) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931.
30. (c) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911.
31. (d) Naumann, C.; Sherman, J. C. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001.
32. (e) Hardie, M. J.; Raston, C. L. J. Chem. Soc., Dalton Trans. 2000, 2483.
33. (f) Rebek, J., Jr. Chem. Commun. 2000, 637.
34. (g) Warmuth, R.; Yoon, J. Acc. Chem. Res. 2001, 34, 95.
35. (h) Mungaroo, R.; Sherman, J. C. Chem. Commun. 2002, 1672.
36. (a) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: London, 2000.
37. (b) Calixarenes in Action; Mandolini, L., Ungaro, R., Eds.; Imperial College Press: London, 2000.
38. (c) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001.
39. (d) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
40. (e) Fan, M.; Zhang, H.; Lattman, M. Chem. Commun. 1998, 99.
41. (f) Yu, S.-Y.; Huang, H.; Liu, H.-B.; Chen, Z.-N.; Zhang, R.; Fujita, M. Angew. Chem., Int. Ed. 2003, 42, 686.
42. (g) Macrocycle Synthesis: A Practical Approach; Parker, D., Ed.; Oxford University Press: Oxford, 1996.
43. (a) Kobayashi, K.; Shirasaka, T.; Yamaguchi, K.; Sakamoto, S.; Horn, E.; Furukawa, N. Chem. Commun. 2000, 41.
44. (b) Shimizu, K. D.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12403.
45. (c) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
46. (d) Mogck, O.; Bohmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489.
47. (e) Gibb, C. L. D.; Stevens, E. D.; Gibb, B. C. J. Am. Chem. Soc. 2001, 123, 5849.
48. (a) MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. 1999, 38, 1018.
49. (b) Gibb, C. L. D.; Stevens, E. D.; Gibb, B. C. Chem. Commun. 2000, 363.
50. The use of single-metal atom units to create calix[n]arene or resorc[n]-arene cages has been reported, but the number of structurally characterized molecules is very limited. See, for example: (a) Fox, O. D.; Dalley, N. K.; Harrison, R. G. J. Am. Chem. Soc. 1998, 120, 7111.
51. (b) Fox, O. D.; Dalley, N. K.; Harrison, R. G. Inorg. Chem. 1999, 38, 5860.
52. (c) Fochi, F.; Jacopozzi, P.; Wegelius, E.; Rissanen, K.; Cozzini, P.; Marastoni, E.; Fisicaro, E.; Manini, P.; Fokkens, R.; Dalcanale, E. J. Am. Chem. Soc. 2001, 123, 7539.
53. (d) Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2000, 39, 136.
54. Catalan, K. V.; Mindiola, D. J.; Ward, D. L.; Dunbar, K. R. Inorg. Chem. 1997, 36, 2458.
55. Chisholm, M. H.; Cotton, F. A.; Daniels, L. M.; Folting, K.; Huffman, J. ; Iyer, S.; Lin, C.; MacIntosh, A. M.; Murillo, C. A. J. Chem. Soc., Dalton Trans. 1999. 1387.
56. (a) Larsen, M.; Jrrgensen, M. J. Org. Chem. 1996, 61, 6661.
57. (b) Sansone, F.; Barboso, S.; Casnati, A.; Fabbi, M.; Pochini, A.; Ugozzoli, F.; Ungaro, R. Eur. J. Org. Chem. 1998, 897.
58. (c) Gutsche, C. D.; Pagoda, P. F. J. Org. Chem. 1985, 50, 5795.
59. 2 molecule is formed by reaction of acetonitrile with water, in a process that is known to be catalyzed by transition metal species. (See, for example: Eglin, J. E. Comments Inorg. Chem. 2002, 23, 23 and references therein.) Other crystallographic data for 1c and 1b are essentially the same, and they are provided in the Supporting Information.
60. SAINT. Data Reduction Software. Version 6.36A; Bruker Advanced X-ray Solutions, Inc.: Madison, WI, 2001.
61. SADABS, Version 2.05; Area Detector Absorption and Other Corrections; Bruker Advanced X-ray Solutions, Inc.: Madison, WI, 2001.
62. Sheldrick, G. M. SHELXTL. Version 6.12; Bruker Advanced X-ray Solutions, Inc.: Madison, WI, 2002.
63. Crystals of la were obtained from a reaction similar to that described for the synthesis of 1b, except that the reaction was done at 22 °C over a period of 2 days, and without chromatographic purification.
64. These crystals were prepared, as reported above, by taking single crystals of the acetonitrile analogue and rinsing them with distilled water.
65. Cotton, F. A.; Hillard, E. A.; Liu, C. Y.; Murillo, C. A.; Wang, W.; Wang, X. Inorg. Chim. Acta 2002, 337, 233.
66. Bonar-Law, R. P.; McGrath, T. D.; Singh, N.; Bickley, J. F.; Steiner, A. Chem. Commun. 1999, 2457.
67. Berry, J. F.; Cotton, F. A.; Ibragimov, S. A.; Murillo, C. A.; Wang, X. J. Chem. Soc., Dalton Trans. 2003, 4297.
68. Cotton, F. A.; Walton, R. A. Multiple Bonds between Metal Atoms, 2nd ed. ; Oxford University Press: Oxford, 1993.
69. (a) Cotton, F. A.; Hillard, E. A.; Murillo, C. A. J. Am. Chem. Soc. 2002, 124, 5658.
70. (b) Johnson, S. A.; Hunt, H. R.; Neumann, H. M. Inorg. Chem. 1963, 2, 960.
71. (c) Trexler, J. W., Jr.; Schreiner, A. F.; Cotton, F. A. Inorg. Chem. 1988, 27, 3265.
72. (d) Miskowski, V. M.; Schaefer, W. P.; Sadeghi, B.; Santarsiero, B. D.; Gray, H. B. Inorg. Chem. 1984, 23, 1154.
73. (e) Lichtenberger, D. L.; Pollard, J. R.; Lynn, M. A.; Cotton, F. A.; Feng, X. J. Am. Chem. Soc. 2000, 122, 3182.
74. + cation, for which extensive characterization was done.
75. See, for example: Cotton, F. A.; Daniels, L. M.; Lei, P.; Murillo, C. A. ; Wang, X. Inorg. Chem. 2001, 40, 2778 and references therein.
76. (a) Caulder, D. L.; Brückner, C.; Powers, R. E.; König, S.; Parac, T. N.; Leary, J. A.; Raymond, K. N. J. Am. Chem. Soc. 2001, 123, 8923.
77. (b) Parac, T. N.; Caulder, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1998, 120, 8003.
78. (c) Vysotsky, M. O.; Pop, A.; Broda, F.; Thondorf, I.; Böhmer, V. Chem.-Eur. J. 2001, 7, 4403.
79. (a) Aoki, S.; Shiro, M.; Kimura, E. Chem.-Eur. J. 2002, 8, 929.
80. (b) Chopra, N; Sherman, J. C. Angew. Chem., Int. Ed. 1999, 38, 1955.
81. (c) Chapman, R. G.; Sherman, J. C. J. Org. Chem. 2000, 65, 513.
82. (d) Fox, O. D.; Leung, J. F.-Y.; Hunter, J. M.; Dalley, N. K.; Harrison, R. G. Inorg. Chem. 2000, 39, 783.
83. (e) Atwood, J. L.; Szumna, A. J. Am. Chem. Soc. 2002, 124, 10646.
84. (f) Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 4928.
85. (g) Ikeda, A.; Yoshimura, M.; Udzo, H.; Fukuhara, C.; Shinkai, S. J. Am. Chem. Soc. 1999, 121, 4296.
86. (h) Park, S. J.; Hong, J.-I., Chem. Commun. 2001, 1554.
87. (i) Zhong, Z.; Ikeda, A.; Ayabe, M.; Shinkai, S.; Sakamoto, S.; Yamaguchi, K. J. Org. Chem. 2001, 66, 1002.
88. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. Part A: Theory and Applications in Inorganic Chemistry, 5th ed.; John Wiley & Sons: New York, 1997.
89. (a) Vincenti, M.; Irico, A. Int. J. Mass Spectrom. 2002, 214, 23.
90. (b) Schalley, C. A.; Castellano, R. K.; Brody, M. S.; Rudkevich, D. M.; Siuzdak, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 4568.
91. For a review of calixarenes with dimetal units up to the year 2001, see: Cotton, F. A.; Daniels, L. M.; Lin, C.; Murillo, C. A. Inorg. Chim. Acta 2003, 347, 1.
92. (a) Acho, J. A.; Lippard, S. J. Inorg. Chim. Acta 1995, 229, 5.
93. (b) Acho, J. A.; Ren, T.; Yun, J. W.; Lippard, S. J. Inorg. Chem. 1995, 34, 5226.
94. See, for example: (a) Chisholm, M. H.; Folting, K.; Streib, W. E.; Wu, D.-D. Inorg. Chem. 1999, 38, 5219.
95. (b) Caselli, A.; Solari, A. R.; Scopelliti, L. R.; Floriani, C.; Re, N.; Rizzoli, A. C.; Chiesi-Villa, A. J. Am. Chem. Soc. 2000, 122, 3652.
96. Seltz, J.; Maas, G. Chem. Commun. 2002, 338.