A combined theoretical-experimental study of the inclusion of niobocene dichloride in native and permethylated β-cyclodextrins

Organometallics

Volumn 26, Issue 17, 2007, Pages 4220-4228

  Pereira, Cláudia C L ^a   Nolasco, Maneia ^a   Braga, Susana S ^a   Almeida Paz, Filipe A ^a   Ribeiro Claro, Paulo ^a   Pillinger, Martyn ^a   Gonçalves, Isabel S ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; CYCLODEXTRINS; METAL COMPLEXES; THERMOGRAVIMETRIC ANALYSIS; VIBRATIONAL SPECTRA; X RAY POWDER DIFFRACTION;

CRYSTALLINITY; NIOBOCENE DICHLORIDE; VIBRATIONAL MODES;

ORGANOMETALLICS;

EID: 34548191021     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7003749     Document Type: Article

References (94)

1. Harata, K. In Comprehensive Supramolecular Chemistry; Szejtli, J., Osa, T., Eds.; Pergamon: Oxford, 1996; Vol. 3, pp 279-304.
2. Saenger, W.; Steiner, T. Acta Crystallogr. 1998, A54, 798.
3. Szejtli, J. Chem. Rev. 1998, 98, 1743.
4. Saenger, W. Angew. Chem., Int. Ed. Engl. 1980, 79, 344.
5. Fenyvesi, E.; Szente, L.; Russel, N. R.; McNamara, M. In Comprehensive Supramolecular Chemistry; Szejtli, J., Osa, T., Eds.; Pergamon: Oxford, 1996; Vol. 3, pp 305-366.
6. (a) Hapiot, F.; Tilloy, S.; Monflier, E. Chem. Rev. 2006, 106, 767.
7. (b) Sliwa, W.; Girek, T. Heterocycles 2003, 60, 2147.
8. Alston, D. R.; Ashton, P. R.; Lilley, T. H.; Stoddart, J. F.; Zarzycki, R.; Slawin, A. M. Z.; Williams, D. J. Carbohydr. Res. 1989, 192, 259.
9. (a) Breslow, R.; Trainor, G.; Ueno, A. J. Am. Chem. Soc. 1983, 105, 2739.
10. (b) Matsue, T.; Evans, D. H.; Osa, T.; Kobayashi, N. J. Am. Chem. Soc. 1985, 107, 3411.
11. (c) Harada, A.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 645.
12. (d) Harada, A.; Hu, Y.; Yamamoto, S.; Takahashi, S. J. Chem. Soc., Dalton Trans. 1988, 729.
13. (e) Odagaki, Y.; Hirotsu, K.; Higuchi, T.; Harada, A.; Takahashi, S. J. Chem. Soc., Perkin Trans. 1990, 7, 1230.
14. (f) Liu, Y.; Zhong, R.-Q.; Zhang, H.-Y.; Song, H.-B. Chem. Commun. 2005, 2211.
15. (g) Ju, H.; Leech, D. Langmuir 1998, 74, 300.
16. (h) Kaifer, A. E. Acc Chem. Res. 1999, 32, 62.
17. (i) Coutouli-Argyropoulou, E.; Kelaidopoulou, A.; Sideris, C.; Kokkinidis, G. J. Electroanal. Chem. 1999, 477, 130.
18. (j) Osella, D.; Carretta, A.; Nervi, C.; Ravera, M.; Gobetto, R. Organometallics 2000, 79, 2791.
19. (k) Fernandes, J. A.; Lima, S.; Braga, S. S.; Ribeiro-Claro, P.; Rodriguez-Borges, J. E.; Teixeira, C.; Pillinger, M.; Teixeira-Dias, J. J. C.; Gonçalves, I. S. J. Organomet. Chem. 2005, 690, 4801.
20. (l) Fernandes, J. A.; Lima, S.; Braga, S. S.; Pillinger, M.; Rodriguez-Borges, J. E.; Ribeiro-Claro, P.; Teixeira-Dias, J. J. C.; Gonçalves, I. S. Eur. J. Inorg. Chem. 2005, 4729.
21. (m) Fernandes, J. A.; Lima, S.; Braga, S. S.; Pillinger, M.; Ribeiro-Claro, P.; Rodriguez-Borges, J. E.; Lopes, A. D.; Teixeira-Dias, J. J. C.; Gonçalves, I. S. Organometallics 2005, 24, 5673.
22. (a) Turel, I.; Demsar, A.; Košmrlj, J. J. Inclusion Phenom. Macrocyclic Chem. 1999, 35, 595.
23. (b) Vinklárek, J.; Honzíèek, J.; Holubová, J. Central Eur. J. Chem. 2005, 3, 72.
24. (c) Braga, S. S.; Gonçalves, I. S.; Pillinger, M.; Ribeiro-Claro, P.; Teixeira-Dias, J. J. C. J. Organomet. Chem. 2001, 632, 11.
25. (d) Braga, S. S.; Marques, M. P. M.; Sousa, J. B.; Pillinger, M.; Teixeira-Dias, J. J. C.; Gonçalves, I. S. J. Organomet. Chem. 2005, 690, 2905.
26. Meister, G.; Stoeckli-Evans, H.; Süss-Fink, G. J. Organomet. Chem. 1993, 453, 249.
27. Klingert, B.; Rihs, G. J. Chem. Soc., Dalton Trans. 1991, 2749.
28. (a) Shimada, M.; Harada, A.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1991, 263.
29. (b) Patel, P. P.; Welker, M. E. J. Organomet. Chem. 1997, 547, 103.
30. (c) Díaz, C.; Arancibia, A. J. Inclusion Phenom. Macrocyclic Chem. 1998, 30, 127.
31. (d) Braga, S. S.; Gonçalves, I. S.; Ribeiro-Claro, P.; Lopes, A. D.; Pillinger, M.; Teixeira-Dias, J. J. C.; Rocha, J.; Romão, C. C. Supramol Chem. 2002, 14, 359.
32. (e) Braga, S. S.; Almeida Paz, F. A.; Pillinger, M.; Seixas, J. D.; Romão, C. C.; Gonçalves, I. S. Eur. J. Inorg. Chem. 2006, 1662.
33. (f) Alston, D. R.; Slawin, A. M. Z.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 786.
34. (g) Song, L.; Meng, Q.; You, X. J. Organomet. Chem. 1995, 498, Cl.
35. (h) Harada, A.; Saeki, K.; Takahashi, S. Organometallics 1989, 8, 730.
36. (i) Braga, S. S.; Gago, S.; Seixas, J. D.; Valente, A. A.; Pillinger, M.; Santos, T. M.; Gonçalves, I. S.; Romão, C. C. Inorg. Chim. Acta 2006, 359, 4757.
37. (j) Braga, S. S.; Gonçalves, I. S.; Lopes, A. D.; Pillinger, M.; Rocha, J.; Romão, C. C.; Teixeira-Dias, J. J. C. J. Chem. Soc., Dalton Trans. 2000, 2964.
38. (k) Lima, S.; Gonçalves, I. S.; Ribeiro-Claro, P.; Pillinger, M.; Lopes, A. D.; Ferreira, P.; Teixeira-Dias, J. J. C.; Rocha, J.; Romão, C. C. Organometallics 2001, 20, 2191.
39. (l) Pereira, C. C. L.; Braga, S. S.; Almeida Paz, F. A.; Pillinger, M.; Klinowski, J.; Gonçalves, I. S. Eur. J. Inorg. Chem. 2006, 4278.
40. Bioorganometallics: Biomolecules, Labeling, Medicine; Jaouen, G., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
41. (a) Davis, M. E.; Brewster, M. E. Nat. Rev. Drug Discovery 2004, 3, 1023.
42. (b) Challa, R.; Ahuja, A.; Ali, J.; Khar, R. K. AAPS PharmSciTech. 2005, 6, E329.
43. (c) Utsuki, T.; Brem, H.; Pitha, J.; Loftsson, T.; Kristmundsdottir, T.; Tyler, B. M.; Olivi, A. J. Controlled Release 1996, 40, 251.
44. (d) Burgos, A. E.; Belchior, J. C.; Sinisterra, R. D. Biomaterials 2002, 23, 2519.
45. (a) Harding, M. M.; Mokdsi, G. Curr. Med. Chem. 2000, 7, 1289.
46. (b) Vinklárek, J.; Paláěková, H.; Honzíèek, J.; Holubová, J.; Holèapek, M.; Císaøová, I. Inorg. Chem. 2006, 45, 2156, and references therein.
47. (a) Caira, M. R. Rev. Roum. Chim. 2001, 46, 371.
48. (b) Schneider, H.-J.; Hacket, F.; Rüdiger, V. Chem. Rev. 1998, 98, 1755.
49. (c) Carón, L.; Christine, C.; Tilloy, S.; Monflier, E.; Landy, D.; Fourmentin, S.; Surpateanu, G. Supramol Chem. 2002, 74, 11.
50. (a) Lipkowitz, K. B. Chem. Rev. 1998, 98, 1829.
51. (b) Bonnet, P.; Jaime, C.; Morin-Allory, L. J. Org. Chem. 2002, 67, 8602.
52. (c) Bonnet, P.; Beà, I.; Jaime, C.; Morin-Allory, L. Supramol. Chem. 2003, 75, 251.
53. (d) Alcaro, S.; Battaglia, D.; Ortuso, F. ARKIVOC 2004, Part (v), 107.
54. (e) Faucci, M. T.; Melani, F.; Mura, P. Chem. Phys. Lett. 2002, 358, 383.
55. (f) Varady, J.; Wu, X.; Wang, S. J. Phys. Chem. B 2002, 106, 4863.
56. (g) Granados, A. M.; de Rossi, R. H.; Barbiric, D. J.; Castro, E. A. J. Mol. Struct. (THEOCHEM) 2002, 679, 91.
57. Harding, M. M.; Prodigalidad, M.; Lynch, M. J. J. Med. Chem. 1996, 39, 5012.
58. Petrovski, Z.; Braga, S. S.; Santos, A. M.; Rodrigues, S. S.; Gonçalves, I. S.; Pillinger, M.; Kühn, F. E.; Romão, C. C. Inorg. Chim. Acta 2005, 358, 981.
59. Boultif, A.; Louer, D. J. Appl. Crystallogr. 2004, 37, 724.
60. LeBail, A.; Duroy, H.; Fourquet, J. L. Mater. Res. Bull. 1988, 23, 447.
61. (a) Allen, F. H. Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 380.
62. (b) Allen, F. H.; Motherwell, W. D. S. Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 407.
63. CSD refcodes of TRIMEB inclusion complexes: ASIQOI, ASIQUO, AZOYOD, BIFGIH, BIFGON, BIFGUT, CAMPIP, CAMPIPlO, COYXAP, COYXAPlO, COYXET, COYXETlO, COYXET20, EKOGOA, EKOGUG, EZAVOQ, FEXBUG, GELKEN, GELKEN10, HEZWAK, HEZWAK01, MODHUI, NIZHAF, PAFSOE, PINMAA, QOYLIZ, RONWOG, WAGLOG, WAGLUM, XAQJII, XAQJII01, ZIFQOU.
64. CSD refcodes of monoclinic TRTMEB inclusion complexes: ASIQOI, ASIQUO, BIFGON, EKOGUG, EZAVOQ, FEXBUG.
65. (a) Rodriguez-Carvajal, J. FULLPROF - A Program for Rietveld Refinement and Pattern Matching Analysis, Abstract of the Satellite Meeting on Powder Diffraction of the XV Congress of the IUCR; Toulouse, France, 1990; p 127.
66. (b) Roisnel, T.; Rodriguez-Carvajal, J. WinPLOTR [June 2005] - A Windows Tool for Powder Diffraction Pattern Analysis, Proceedings of the Seventh European Powder Diffraction Conference (EPDIC 7), Mater. Sci. Forum 2001, 378-381, 118-123.
67. (a) Boultif, A.; Louer, D. J. Appl. Crystallogr. 1991, 24, 987.
68. (b) Louer, D. In Automatic Indexing: Procedures and Applications, Accuracy in Powder Diffraction II; Gaithersburg, MD, 1992; pp 92-104.
69. Laugier, J.; Bochu, B. CHECKCELL - A Software Performing Automatic Cell/Space Group Determination, Collaborative Computational Project Number 14 (CCP14); Laboratoire des Matériaux et du Génie Physique de l'Ecole Supérieure de Physique de Grenoble (INPG): France, 2000.
70. (a) Favre-Nicolin, V.; Cerný, R. J. Appl. Crystallogr. 2002, 35, 734.
71. (b) Favre-Nicolin, V.; Cerný, R. FOX - A Program for ab Initio Structure Solution from Powder Diffraction Data, Program Developed for the Swiss National Science Foundation; University of Geneva: Geneva, Switzerland, 2000.
72. Walters, P.; Stahl, M. BABEL Version 1.3-A Program for the Interconversion of File Formats Used in Molecular Modelling; Department of Chemistry, University of Arizona: Tucson, AZ, 1996.
73. Prout, K.; Cameron, T. S.; Forder, R. A. Acta Crystallogr., Sect. B: Struct. Sci. 1974, 30, 2290.
74. Tsorteki, F.; Bethanis, K.; Mentzafos, D. Carbohydr. Res. 2004, 339, 233.
75. Caira, M. R.; Hunter, R.; Bourne, S. A.; Smith, V. J. Supramol. Chem. 2004, 16, 395.
76. Caira, M. R.; Bourne, S. A.; Mhlongo, W. T.; Dean, P. M. Chem. Commun. 2004, 2216.
77. (a) March, A. Z. Kristallogr. 1932, 87, 285.
78. (b) Dolíase, W. A. J. Appl. Crystallogr. 1986, 19, 267.
79. (a) Gidley, M. J.; Bociek, S. M. J. Am. Chem. Soc. 1988, 110, 3820.
80. (b) Heyes, S. J.; Clayden, N. J.; Dobson, C. M. Carbohydr. Res. 1992, 233, 1.
81. (c) Veregin, R. P.; Fyfe, C. A.; Marchessault, R. H.; Tayler, M. G. Carbohydr. Res. 1987, 760, 41.
82. Cunha-Silva, L.; Teixeira-Dias, J. J. C. New J. Chem. 2005, 29, 1335.
83. Brown, G. R.; Caira, M. R.; Nassimbeni, L. R.; van Oudtshoorn, B. J. Inclusion Phenom. Macrocyclic Chem. 1996, 26, 281.
84. (a) Johnson, J. R.; Shankland, N.; Sadler, I. H. Tetrahedron 1985, 47, 3147.
85. (b) Yamamoto, Y.; Onda, M.; Takahashi, Y.; Inoue, Y.; Chûjô, R. Carbohydr. Res. 1987, 170, 229.
86. Holubová, J.; Černošek, Z.; Pavlík, I. Vib. Spectrosc. 1997, 74, 147.
87. Casadesús, R.; Moreno, M.; González-Lafont, À A.; Lluch, J. M.; Repasky, M. P. J. Comput. Chem. 2004, 25, 99.
88. Curtis, M. D.; Bell, L. G.; Butler, W. M. Organometallics 1985, 4, 701.
89. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. GAUSSIAN 03, Revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
90. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
91. NIST Computational Chemistry Comparison and Benchmark Database, NIST Standard Reference Database Number 101, Release 12, Aug 2005, Johnson, R. D., III, Ed.; http://srdata.nist.gov/cccbdb.
92. (a) Stevens, W. J.; Basch, H.; Krauss, M. J. Chem. Phys. 1984, 81, 6026.
93. (b) Stevens, W. J.; Krauss, M.; Basch, H.; Jasien, P. G. Can. J. Chem. 1992, 70, 612.
94. Braga, S. S.; Aree, T.; Imamura, K.; Vertut, P.; Boal-Palheiros, I.; Saenger, W.; Teixeira-Dias, J. J. C. J. Inclusion Phenom. Macrocyclic Chem. 2002, 43, 115.