Hemibuckminsterfullerene C30H12: X-ray crystal structures of the parent hydrocarbon and of the two-dimensional organometallic network {[Rh2(O2CCF3)4] 3·(C30H12)}

Angewandte Chemie - International Edition

Volumn 43, Issue 41, 2004, Pages 5477-5481

  Petrukhina, Marina A ^a   Andreini, Kristian W ^a   Peng, Lingqing ^b   Scott, Lawrence T ^b  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b BOSTON COLLEGE   (United States)

Author keywords

Arene ligands; Carboxylate ligands; Geodesic polyarenes; Pi interactions; Rhodium

Indexed keywords

CRYSTALLIZATION; FULLERENES; TRANSITION METALS;

METAL CLUSTERS; MONOMETALS;

ORGANOMETALLICS;

CARBOXYLIC ACID; CHRYSENE; CORANNULENE; FLUORINE; FULLERENE DERIVATIVE; HEMIFULLERENE; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; SOLID STATE; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; FULLERENES; HYDROCARBONS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM;

EID: 8444222002     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460855     Document Type: Article

References (41)

1. a) H. W. Kroto, J. R. Heath, S. C. O'Brien, R. F. Curl, R. E. Smalley, Nature 1985, 318, 162;
2. b) W. Kratschmer, L. D. Lamb, K. Fostiropoulos, D. R. Huffman, Nature 1990, 347, 354.
3. a) P. W. Rabideau, A. Sygula in Advances in Theortically Interesting Molecules, Vol. 3 (Ed.: R. P. Thummel), JAI, Greenwich, 1995, p. 1;
4. b) P. W. Rabideau, A. Sygula, Acc. Chem. Res. 1996, 29, 235;
5. c) L. T. Scott, Pure Appl. Chem. 1996, 68, 291;
6. d) G. Mehta, H. S. P. Rao, Adv. Strain Org. Chem. 1997, 6, 139;
7. e) G. Mehta, H. S. P. Rao, Tetrahedron 1998, 54, 13325;
8. f) L. T. Scott, H. E. Bronstein, D. V. Preda, R. B. M. Ansems, M. S. Bratcher, S. Hagen, Pure Appl. Chem. 1999, 71, 209.
9. a) T. J. Seiders, K. K. Baldridge, J. M. O'Connor, J. S. Siegel, J. Am. Chem. Soc. 1997, 119, 4781;
10. b) C. M. Alvarez, R. J. Angelici, A. Sygula, R. Sygula, P. W. Rabideau, Organometallics 2003, 22, 624.
11. M. A. Petrukhina, K. W. Andreini, J. Mack, L. T. Scott, Angew. Chem. 2003, 115, 3497; Angew. Chem. Int. Ed. 2003, 42, 3375.
12. M. A. Petrukhina, K. W. Andreini, J. Mack, L. T. Scott, Angew. Chem. 2003, 115, 3497; Angew. Chem. Int. Ed. 2003, 42, 3375.
13. a) R. Faust, K. P. C. Vollhardt, J. Chem. Soc. Chem. Commun. 1993, 1471;
14. b) M. J. Plater, H. S. Rzepa, S. Stossel, J. Chem. Soc. Chem. Commun. 1994, 1567;
15. c) F. Geneste, A. Moradpour, G. Dive, D. Peelers, J. Malthête, J.-F. Sadoc, J. Org. Chem. 2002, 67, 605.
16. a) A. H. Abdourazak, Z. Marcinow, A. Sygula, R. Sygula, P. W. Rabideau, J. Am. Chem. Soc. 1995, 117, 6410;
17. b) For later syntheses, see also G. Mehta, G. Panda, P. V. V. Srirama Sarma, Tetrahedron Lett. 1998, 39, 5835 and ref [9].
18. For calculations on binding of metal centers by 2, see a) J. Plater, H. S. Rzepa, F. Stoppa, S. Stossel, J. Chem. Soc. Perkin Trans. 2 1994, 3, 399;
19. b) A. Sygula, P. W. Rabideau, J. Chem. Soc. Chem. Commun. 1994, 2271;
20. c) F. Nunzi, A. Sgamellotti, N. Re, Organometallics 2002, 21, 2219.
21. R. M. Shaltout, R. Sygula, A. Sygula, F. R. Fronczek, G. G. Stanley, P. W. Rabideau, J. Am. Chem. Soc. 1998, 120, 835.
22. S. Hagen, M. S. Bratcher, M. S. Erikson, G. Zimmermann, L. T. Scott, Angew. Chem. 1997, 109, 407; Angew. Chem. Int. Ed. Engl. 1997, 36, 406.
23. S. Hagen, M. S. Bratcher, M. S. Erikson, G. Zimmermann, L. T. Scott, Angew. Chem. 1997, 109, 407; Angew. Chem. Int. Ed. Engl. 1997, 36, 406.
24. 3, 22 °C): δ = 7.37 (dd, 3 H), 7.61 (d, 3H), 7.65 (d, 3H), 7.83 ppm (s, 3H).
25. 2 converged at R1 = 0.0333 and wR2 = 0.0687 for 77 parameters and 462 reflections with I > 2σ(I) (R1 = 0.0423, wR2 = 0.0718 for 542 unique reflections) and a GOF of 1.072. CCDC-238109 and CCDC-238110 (2-o and 2-t) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+ 44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
26. J. C. Hanson, C. E. Nordman, Acta Crystallogr. Sect. B 1976, 32, 1147.
27. a) L. T. Scott, M. S. Bratcher, S. Hagen, J. Am. Chem. Soc. 1996, 118, 8743;
28. b) R. B. M. Ansems, L. T. Scott, J. Am. Chem. Soc. 2000, 122, 2719;
29. D. M. Forkey, S. Attar, B. C. Noll, R. Koerner, M. M. Olmstead, A. L. Balch, J. Am. Chem. Soc. 1997, 119, 5766.
30. 12 bowl (2) pictured in Figure 1 would be designated as M, assuming that the concave surface is facing the reader.
31. F. A. Cotton, E. V. Dikarev, X. Feng, Inorg. Chim. Acta 1995, 237, 19.
32. a) F. A. Cotton, E. V Dikarev, M. A. Petrukhina, S.-E. Stiriba, Polyhedron 2000, 19, 1829;
33. b) F. A. Cotton, E. V Dikarev, M. A. Petrukhina, J. Am. Chem. Soc. 2001, 123, 11655.
34. 3, 22 °C): δ = 7.37 (dd, 3 H), 7.61 (d, 3 H), 7.65(d, 3H), 7.83 ppm (s, 3H).
35. 2 converged at R1 =0.0613 and wR2 = 0.1092 for 412 parameters, 30 restraints, and 2375 reflections with I > 2σ(I) (R1 = 0.1461, wR2 = 0.1292 for 5169 unique reflections) and a GOF of 0.821. CCDC-238111 contains the supplementary crystallographic data for 3; see ref. [11] for ordering information.
36. a) F. A. Cotton, E. A. Hillard, C. Y. Liu, C. A. Murillo, W. Wang, X. Wang, X. Inorg. Chim. Acta 2002, 337, 233;
37. b) E. V. Dikarev, K. W. Andreini, M. A. Petrukhina, Inorg. Chem. 2004, 43, 3219.
38. a) W. C. Herndon, J. Am. Chem. Soc. 1974, 96, 7605;
39. b) W C. Herndon, C. Parkanyi, J. Chem. Educ. 1976, 53, 689;
40. c) B. F. Plummer, L. K. Steffen, W. C. Herndon, Struct. Chem. 1993, 3, 279.
41. Higher level molecular orbital calculations (B3LYP/6-31G*) predict bond lengths [Å] that correlate approximately with those derived from simple considerations of Pauling bond orders (see Figure 1): a) 1.3917, b) 1.4571, c) 1.4237, d) 1.3908, e) 1.4228, f) 1.3851, g) 1.4342, h) 1.4063, i) 1.3787, j) 1.4424, k) 1.4124, l) 1.5138, m) 1.4278. It is interesting to note that metal complexation is observed at the rim bond with the highest Pauling order (a), in preference even to bonds that are calculated to have shorter lengths (d, f, and i).