Anion binding by a tetradipicolylamine-substituted resorcinarene cavitand

Inorganic Chemistry

Volumn 44, Issue 12, 2005, Pages 4295-4300

  Gardner, Joseph S ^a   Conda Sheridan, Martin ^a   Smith, Dana N ^a   Harrison, Roger G ^a   Lamb, John D ^a  

^a N243 Eyring Science Center   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CAVITAND; DRUG DERIVATIVE; ETHER DERIVATIVE; PHENYLALANINE; PICOLINE DERIVATIVE; RESORCINARENE; RESORCINOL DERIVATIVE;

ALGORITHM; ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION;

ALGORITHMS; ANIONS; BINDING SITES; ETHERS, CYCLIC; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHENYLALANINE; PICOLINES; RESORCINOLS;

EID: 20744440799     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic048841k     Document Type: Article

References (48)

1. (a) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
2. (b) Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221.
3. (c) Choi, K.; Hamilton, A. D. Coord. Chem. Rev. 2003, 240, 101-110.
4. (d) Llinares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57-75.
5. (e) Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17-55.
6. (f) Best, M. D.; Tobey, S. L.; Anslyn, E. V. Coord. Chem. Rev. 2003, 240, 3-15.
7. (g) Beer, P. D.; Hayes, E. J. Coord. Chem. Rev. 2003, 240, 167-189.
8. (a) Stadler-Szoke, A.; Szejtli, J. Acta Pharm. Hung. 1979, 49, 30-34.
9. (b) Szejtli, J.; Gerloczy, A.; Szente, L.; Banky-Elod, E.; Sebestyen, G. ; Fonagy, A.; Kurcz, M. Acta Pharm. Hung. 1979, 49, 207-21.
10. Sessler, J. L.; Katayev, E.; Pantos, G. D.; Ustynyuk, Y. A. Chem. Commun. 2004, 11, 1276-1277.
11. (a) Mangani, S.; Ferraroni, M. In Supramolecular Chemistry of Anionx; Bianchi, A., Bowman-James, K., Garcia-Espana, E., Eds.; Wiley-VCH: New York, 1997; Chapter 3.
12. (b) Beer, P. D.; Gale, P. A.; Smith, D. K. Supramolecular Chemistry; Evans J., Ed.; Oxford Chemistry Primers; Oxford Uni. Press: New York, 1999; Chapter 3.
13. (c) Dudziuk. H. Introduction to Supramolecular Chemistry: Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002; Chapter 7.8.
14. (d) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; John Wilev & Sons Ltd.: New York, 2000; Chapter 4.
15. (a) Mason, S.; Llinares, J. M.; Morton, M.; Clifford, T.; Bowman-James, K. J. Am. Chem. Soc. 2000, 122, 1814-1815.
16. (b) Mason, S.; Clifford, T.; Seib, L.; Kuczera, K.; Bowman-James, K. J. Am. Chem. Soc. 1998, 120, 8899-8900.
17. (c) Hossain, M. A.; Llinares, J. M.; Powell, D.; Bowman-James, K. Inorg. Chem. 2001, 40, 2936-2937.
18. (d) Hossain, M. A.; Kang, S. O.; Powell, D.; Bowman-James, K. Inorg. Chem. 2003, 42, 1397-1399.
19. (e) Kang, S. O.; Llinares, J. M.; Powell, D.; VanderVelde, D.; Bowman-James, K. J. Am. Chem. Soc. 2003, 125, 10152-10153.
20. (f) Morehouse, P.; Hossain, A.; Llinares, J. M.; Powell, D.; Bowman-James, K. Inorg. Chem. 2003, 42, 8131-8133.
21. (g) Hossain, A.; Kang, S. O.; Llinares, J. M.; Powell, D.; Bowman-James, K. Inorg. Chem. 2003, 42, 5043-5045.
22. (a) Tobey, S. L.; Jones, B. D.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 4026-4027.
23. (b) Tobey, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 14807-14815.
24. (c) Folmer-Anderson, J. F.; Ait-Haddou, H.; Lynch, V. M.; Anslyn, E. V. Inorg. Chem. 2003, 42, 8674-8681.
25. (d) Tobey, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 10963-10970.
26. (e) Tobey, S. L.; Anslyn, E. V. Org. Lett. 2003, 5, 2029-2031.
27. Gokel, G. W., Ed.; Comprehensive Supramolecular Chemistry; Pergamon: Oxford, 1996; Vol. 1.
28. Niederl, J. B.; Vogel, H. J. J. Am. Chem. Soc. 1940, 62, 2512-2514.
29. Högberk, A. G. S. J. Am. Chem. Soc. 1980, 102, 6046-6050.
30. Moran, J. R.; Karbach, S.; Cram, D. J. J. Am. Chem. Soc. 1982, 104, 5826-5828.
31. Kobayashi, K.; Ishii, K.; Sakamoto, S.; Shirasaka, T.; Yamaguchi, K. J. Am. Chem. Soc. 2003, 125, 10615-10624.
32. Suman, M.; Freddi, M.; Massera, C.; Ugozzoli, F.; Dalcanale, E. J. Am. Chem. Soc. 2003, 125, 12068-12069.
33. Gibb, C. L. D.; Stevens, E. D.; Gibb, B. C. J. Am. Chem. Soc. 2001, 123, 5849-5850.
34. Renslo, A. R.; Tucci, F. C.; Rudkevich, D. M.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 4573-4582.
35. Tucci, F. C.; Rudkevich, D. M.; Rebek, J. Chem. - Eur. J. 2000, 6, 1007-1016.
36. Shivanyuk, A.; Rissanen, K.; Korner, S. K.; Rudkevich, D. M.; Rebek; J. Helv. Chim. Acta 2000, 83, 1778-1790.
37. Kobayashi, K.; Shirasaka, T.; Horn, E.; Furukawa, N.; Yamaguchi, K.; Sakamoto, S. Chem. Commun. 2000, 41-42.
38. Nissink, J. W. M.; Boerrigter, H.; Verboom, W.; Reinhoudt, D. N.; Van der Maas; J. H. J. Chem. Soc., Perkin Trans 2 1998, 2541-2546.
39. (a) Boerrigter, H.; Grave, L.; Nissink, J. W. M.; Chrisstoffels, L. A. J.; van der Mass, J. H.; Verboom, W.; de Jong, F.; Reinhoudt, D. N. J. Org. Chem. 1998, 63, 4174-4180.
40. (b) Hayashida, O.; Shivanyuk, A.; Rebek, J. Angew. Chem., Int. Ed. 2002, 41, 3423-3426.
41. (c) Sebo, L.; Diederich, F. Helv. Chim. Acta 2000, 83, 93-113.
42. Rudkevich, D. M.; Himersson, G.; Rebek, J. J. Am. Chem. Soc. 1997, 119, 9911-9912.
43. Lücking, U.; Rudkevich, D. M.; Rebek, J., Jr. Tetrahedron Lett. 2000, 47, 9547-9551.
44. (a) Atwood, J. L.; Szumna A. Chem. Commun. 2003, 940-941.
45. (b) Atwood, J. L.; Szumna A. J. Am. Chem. Soc. 2002, 124, 10646-10647.
46. Fox, O. D.; Dalley, N. K.; Harrison, R. G. Inorg. Chem. 2000, 39, 620-622.
47. Connors, K. A. Binding Constants the Measurement of Molecular Complex Stability; Wiley & Sons: New York, 1987; pp 189-216.
48. Modeling of cavitand-anion complexes was performed using PC Spartan Pro and energy minimized using semiempirical PM3 calculations. The structure with two cavitands and four anions is also possible but has a higher calculated energy than the structure shown.