Complexation of ferrocene derivatives by the cucurbit[7]uril host: A comparative study of the cucurbituril and cyclodextrin host families

Journal of the American Chemical Society

Volumn 127, Issue 37, 2005, Pages 12984-12989

  Jeon, Woo Sung ^b   Moon, Kwangyul ^a   Park, Sang Hyun ^b   Chun, Hyungpil ^b   Ko, Young Ho ^b   Lee, Jin Yong ^d   Lee, Eun Sung ^b   Samal, S ^b   Selvapalam, N ^b   Rekharsky, Mikhail V ^c   Sindelar, Vladimir ^a   Sobransingh, David ^a   Inoue, Yoshihisa ^c   Kaifer, Angel E ^a   Kim, Kimoon ^b  

^a Department of Biology   (United States)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d Chonnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL ATOMIC STRUCTURE; CYCLIC VOLTAMMETRY; DERIVATIVES; ELECTROSTATICS; INCLUSIONS; NEGATIVE IONS; X RAY CRYSTALLOGRAPHY;

CARBOXYLATE GROUPS; CUCURBIT[7]URIL; FERROCENE; X-RAY CRYSTAL STRUCTURE;

COMPLEXATION;

BETA CYCLODEXTRIN; CARBONYL DERIVATIVE; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CUCURBIT[7]URIL; CUCURBITURIL; CYCLODEXTRIN; FERROCENE DERIVATIVE; FERROCENECARBOXYLATE; OXYGEN; RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; CALCULATION; CALORIMETRY; CHEMICAL BINDING; CHEMICAL INTERACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRIC POTENTIAL; ELECTROCHEMISTRY; EQUILIBRIUM CONSTANT; MOLECULAR STABILITY; POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SURFACE PROPERTY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

BRIDGED COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; CYCLODEXTRINS; FERROUS COMPOUNDS; IMIDAZOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; THERMODYNAMICS;

EID: 25144489591     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052912c     Document Type: Article

References (70)

1. (a) Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540.
2. (b) Day, A. I.; Arnold, A. P.; Blanch, R. J.; Snushall, B. J. Org. Chem. 2001, 66, 8094.
3. Freeman, W. A.; Mock, W. L.; Shih, N.-Y. J. Am. Chem. Soc. 1981, 103, 7367.
4. For reviews, see: (a) Mock, W. L. In Comprehensive Supramolecular Chemistry; Vögtle, Ed.; Pergamon: Oxford, 1996; Vol. 2, p 447.
5. (c) Cintas, P. J. Incl. Phenom. 1994, 17, 205.
6. (a) Mock, W. L.; Shih, N.-Y. J. Org. Chem. 1986, 51, 4440.
7. (b) Mock, W. L.; Shih, N.-Y. J. Am. Chem. Soc. 1988, 110, 4706.
8. (c) Mock, W. L.; Shih, N.-Y. J. Am. Chem. Soc. 1989, 111, 2697.
9. (d) Hoffmann, R.; Knoche, W.; Fenn, C.; Buschmann, H.-J. J. Chem. Soc., Faraday Trans. 1994, 90, 1507.
10. (e) Jeon, Y.-M.; Kim, J.; Whang, D.; Kim, K. J. Am. Chem. Soc. 1996, 118, 9790.
11. (f) Whang, D.; Heo, J.; Park, J. H.; Kim, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 78.
12. (g) Haouaj, M. E.; Luhmer, M.; Ko, Y. H.; Kim, K.; Bartik, K. J. Chem. Soc., Perkin Trans. 2 2001, 804.
13. (h) Haouaj, M. E.; Ko, Y. H.; Luhmer, M.; Kim, K.; Bartik, K. J. Chem. Soc., Perkin Trans. 2 2001, 2104.
14. (i) Meschke, C.; Buschmann, H. J.; Schollmeyer, E. Thermochim. Acta 1997, 297, 43.
15. (j) Buschmann, H. J.; Jansen, K.; Schollmeyer, E. Thermochim. Acta 2000, 346, 33.
16. (k) Buschmann, H.-J.; Jansen, K.; Schollmeyer, E. J. Incl. Phenom. 2000, 37, 231.
17. Buschmann, H. J.; Cleve, E.; Jansen, K.; Wego, A.; Schollmeyer, E. J. Incl. Phenom. Macrocyclic Chem. 2001, 40, 117.
18. Marquez, C.; Nau, W. M. Angew. Chem., Int. Ed. 2001, 40, 3155.
19. (n) Marquez. C.; Hudgins, R. R.; Nau, W. M. J. Am. Chem. Soc. 2004, 126, 5806.
20. For reviews, sec: (a) Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621.
21. (b) Kim, K.; Kim, H.-J. In Encyclopedia of Supramolecular Chemistry; Atwood, S., Ed.; Marcel Dekker Inc.: New York, 2004; p 390.
22. (c) Kim, K.; Selvapalam, N.; Oh, D.-H. J. Incl. Phenom. 2004, 50, 31.
23. CB[7] inclusion complexes: (a) Marquez, C.; Nau, W. M. Angew. Chem., Int. Ed. 2001, 40, 4387.
24. (b) Blanch, R. J.; Sleeman, A. J.; White, T. J.; Arnold, A. P.; Day, A. I. Nano Lett. 2002, 2, 147.
25. (c) Kim, H.-J.; Jeon, W. S.; Ko, Y. H.; Kim, K. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5007.
26. (d) Ong, W.; Gomez-Kaifer, M.; Kaifer, A. E. Org. Lett. 2002, 4, 1791.
27. (e) Moon, K.; Kaifer, A. E. Org. Lett. 2004, 6, 185.
28. (f) Ong, W.; Kaifer, A. E. J. Org. Chem. 2004, 69, 1383.
29. (g) Wheate, N. J.; Day, A. I.; Blanch, R. J.; Arnold, A. P.; Cullinane, C.; Collins, J. G. Chem. Commun. 2004, 1424.
30. (h) Jeon, Y. J.; Kim, S.-Y.; Ko, Y. H.; Sakamoto, S.; Yamaguchi, K.; Kim K. Org. Biomol. Chem. 2005, 3, 2122.
31. (i) Marquez, C.; Pischel, U.; Nau, W. M. Org. Lett 2003, 5, 3911.
32. (j) Wagner, B. D.; Stojanovic, N.; Day, A. I.; Blanch, R. J. J. Phys. Chem. B 2003, 107, 10741.
33. CB[8] inclusion complexes: (a) Kim, H.-J.; Heo, J.; Jeon, W. S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 1526.
34. (b) Kim, S.-Y.; Jung, I.-S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 2119.
35. (c) Jon, S. Y.; Ko, Y. H.; Park, S.-H.; Kim, H.-J.; Kim, K. Chem. Commun. 2001, 1938.
36. (d) Lee, J. W.; Kim, K. P.; Choi, S. W.; Ko, Y. H.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Chem. Commun. 2002, 2692.
37. (e) Choi, S.; Park, S. H.; Ziganshina, A. Y.; Ko, Y. H.; Lee, J. W.; Kim, K. Chem. Commun. 2003, 2176.
38. (f) Ziganshina, A. Y.; Ko, Y. H.; Jeon, W. S.; Kim, K. Chem. Commun. 2004, 806.
39. (g) Jeon, Y. J.; Bharadwaj, P. K.; Choi, S. W.; Lee, J. W.; Kim, K. Angew. Chem., Int. Ed. 2002, 41, 4474.
40. (h) Jeon, W. S.; Kim, H.-J.; Lee, C.; Kim, K. Chem. Commun. 2002, 1828.
41. (i) Chubarova, E. V.; Samsonenko, D. G.; Sokolov, M. N.; Gerasko, O. A.; Fedin, V. P.; Platas, J. G. J. Incl. Phenom. 2004, 48, 31.
42. (j) Wu, A.; Isaacs, L. J. Am. Chem. Soc. 2003, 125, 4831.
43. (k) Moon, K.; Grindstaff, J.; Sobransingh, D.; Kaifer, A. E. Angew. Chem., Int. Ed. 2004, 43, 5496.
44. Mukhopadhyay, P.; Wu, A.; Isaacs, L. J. Org. Chem. 2004, 69, 6157.
45. Pattabiraman, M.; Natarajan, A.; Kaanumalle, L. S.; Ramamurthy, V. Org. Lett. 2005, 7, 529.
46. (a) Wenz, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 803.
47. (b) Connors, K. A. Chem. Rev. 1997, 97, 1325.
48. (c) Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875.
49. (d) Szejtli, J. Chem. Rev. 1998, 98, 1743.
50. (a) Inoue, Y.; Hakushi, T.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 475.
51. (b) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637.
52. (a) Buschmann, H.-J.; Cleve, E.; Schollmeyer, E. Inorg. Chim. Acta 1992, 193, 93,
53. (b) Zhang, X. X.; Krakowiak, K. E.; Xue, G.; Bradshaw, J. S.; Izatt, R. M. Ind. Eng. Chem. Res. 2000, 39, 3516.
54. (c) Heo, J.; Kim, J.; Whang, D.; Kim, K. Inorg. Chim. Acta 2000, 279, 307.
55. (d) Sokolov, M. N.; Virovets, A. V.; Dybtsev, D. N.; Gerasko, O. A.; Fedin, V. P.; Hernandez-Molina, R.; Clegg, W.; Sykes, A. G. Angew. Chem., Int. Ed. 2000, 39, 1659.
56. Mirzoian, A.; Kaifer, A. E. Chem. Eur. J. 1997, 3, 1052.
57. Ong, W.; Kaifer, A. E. Organometallics 2003, 22, 4181.
58. (a) Harada, A.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 645.
59. (b) Menger, F. M.; Sherrod, M. J. J. Am. Chem. Soc. 1988, 110, 8606.
60. (c) Thiem, H.-J.; Brandl, M.; Breslow, R. J. Am. Chem. Soc. 1988, 110, 8612.
61. (d) Breslow, R.; Czarniecki, M. F.; Emert, J.; Hamaguchi, H. J. Am. Chem. Soc. 1980, 102, 762.
62. (e) Sigel, B.; Breslow, R. J. Am. Chem. Soc. 1975, 97, 6869.
63. (f) Matsue, T.; Evans, D. H.; Osa, T.; Kobayashi, N. J. Am. Chem. Soc. 1985, 107, 3411.
64. (g) Isnin, R.; Salam, C.; Kaifer, A. E. J. Org. Chem. 1991, 56, 35.
65. (h) Godínez, L. A.; Patel, S.; Criss, C. M.; Kaifer, A. E. J. Phys. Chem. 1995, 99, 17449.
66. (i) Coutouli-Argyropoulou, E.; Kelaidopoulou, A.; Sideris, C.; Kokkinidis, G. J. Electroanal. Chem. 1999, 477, 130.
67. (j) Osella, D.; Carretta, A.; Nervi, C.; Ravera, M.; Gobetto, R. Organometallics 2000, 19, 2791.
68. The ionic composition of the medium is very important in binding studies involving CB[7]. See. for instance: Ong, W.; Kaifer, A. E. J. Org. Chem. 2004, 69, 1383.
69. Kaifer, A. E.; Gómez-Kaifer, M. Supramolecular Electrochemistrvy; Wiley-VCH: Weinheim, 1999; Chapter 9.
70. Frish, M. J.; et al. Gaussian 98, Revision A6; Gaussian Inc.: Pittsburgh, PA, 1999.