Calix[3]amide-based anion receptors: High affinity for fluoride ions and a twisted binding model

Supramolecular Chemistry

Volumn 23, Issue 1-2, 2011, Pages 125-130

  Katagiri, Kosuke ^a   Furuyama, Taniyuki ^b   Masu, Hyuma ^a   Kato, Takako ^a   Matsumura, Mio ^c   Uchiyama, Masanobu ^b,d   Tanatani, Aya ^c   Tominaga, Masahide ^a   Kagechika, Hiroyuki ^e   Yamaguchi, Kentaro ^a   Azumaya, Isao ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^c OCHANOMIZU UNIVERSITY   (Japan)

^d UNIVERSITY OF TOKYO   (Japan)

^e TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

anion receptor; calix 3 amide; DFT calculations

Indexed keywords

EID: 79952213074     PISSN: 10610278     EISSN: 10290478     Source Type: Journal    
DOI: 10.1080/10610278.2010.514909     Document Type: Article

References (48)

1. (a) Caltagirone, C.; Gale, P.A. Chem. Soc. Rev. 2009, 38, 520-563.
2. (b) Steed, J.W. Chem. Commun. 2006, 2637-2649.
3. (c) Beer, P.D.; Gale, P.A. Angew. Chem. Int. Ed. 2001, 40, 486-516.
4. (a) Khatri, V.K.; Upreti, S.; Pandey, S. Org. Lett. 2006, 8, 1755-1758.
5. (b) Hu, H.-Y.; Chen, C.-F. Tetrahedron Lett. 2006, 47, 175-179.
6. (c) Chemielewski, M.J.; Jurczak, J. Chem. Eur. J. 2005, 11, 6080-6094.
7. (d) Chellappan, K.; Singh, N.J.; Hwang, I.-C.; Lee. J.W.; Kim, K.S. Angew. Chem. Int. Ed. 2005, 44, 2899-2903.
8. (e) Sessler, J.L.; Seidel, D. Angew. Chem. Int. Ed. 2003, 42, 5134-5175.
9. (f) Beer, P.D.; Gale, P.A. Angew. Chem. Int. Ed. 2001, 40, 486-516.
10. (g) Gale, P.A. Coord. Chem. Rev. 2003, 240, 191-221.
11. (h) Schmidtchen, F.P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
12. (a) Kay, E.R.; Leigh, D.A.; Zerbetto, F. Angew. Chem. Int. Ed. 2007, 46, 172-191.
13. (b) Muraoka, T.; Kinbara, K.; Aida, T. Nature 2006, 440, 512-515.
14. (c) Pease, A.R.; Jeppesen, J.O.; Stoddart, J.F.; Luo, Y.; Collier, C.P.; Heath, J.R. Acc. Chem. Res. 2001, 34, 433-444.
15. (a) Bryantsev, V.S.; hay, B.P. J. Am. Chem. Soc. 2006, 128, 2035-2042.
16. (b) Miao, R.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Tetrahedron Lett. 2005, 46, 2155-2158.
17. (c) Bondy, C.R.; Gale, P.A.; Loeb, S.J. J. Am. Chem. Soc. 2004, 126, 5030-5031.
18. (d) Chmielewski, M.J.; Charon, M.; Jurzak, J. Org. Lett. 2004, 6, 3501-3504.
19. (e) Nielsen, K.A.; Jeppesen, J.O.; Levillain, E.; Becher, J. Angew. Chem. Int. Ed. 2003, 42, 187-191.
20. (f) Cho, E.J.; Moon, J.W.; Ko, S.W.; Lee, J.Y.; Kim, S.K.; Yoon, J.; nam, K.C. J. Am. Chem. Soc. 2003, 125, 12376-12377.
21. (g) Wallace, K.J.; Belcher, W.J.; Syed, K.F.; seed, J.W. J. Am. Chem. Soc. 2003, 125, 9699-9715.
22. (a) Sergio, E.G.; Claudia, C.; Mark, E.L.; Philip, A.G. Chem. Commun. 2007, 1450-1452.
23. (b) Lang, K.; Curínová, P.; Dudic, M.; Prosková, P.; Stibor, I.; St'astny, V.; Lhoták, P. Tetrahedron Lett. 2005, 46, 4469-4472.
24. (c) Dudic, M.; Lhoták, P.; Stibor, I.; Lang, K.; Prosková, P. Org. Lett. 2003, 5, 149-152.
25. (d) Budka, J.; Lhoták, P.; Michlová. V.; Stibor, I. Tetrahedron Lett. 2001, 42, 1583-1586.
26. (e) Castellano, R.K.; Rebek, Jr., J. J. Am. Chem. Soc. 1998, 120, 3657-3663.
27. (f) Böhmer, V. Angew. Chem. Int. Ed. 1995, 34, 713-745.
28. (g) Scheerder, J.; Fochi, M.; Engbersen, J.F.J.; reinhoudt, D.N. J. Org. Chem. 1994, 59, 7815-7820.
29. (h) Shinkai, S. Tetrahedron 1993, 49, 8933-8968.
30. (i) Gutsche, C.D.; Rogers, J.S.; Stewart, D.; See, K.A. Pure Appl. Chem. 1990, 62, 485-491.
31. (j) Gutsche, C.D. Acc. Chem. Res. 1983, 16, 161-170 .
32. (a) Choi, K.; Hamilton, A.D. J. Am. Chem. Soc. 2003, 125, 10241-10249.
33. (b) Otto, S.; Kubik, S. J. Am. Chem. Soc. 2003, 125, 7804-7805.
34. (a) Amendola, V.; Bergamashi, G.; Boiocchi, M.; Fabbrizzi, L.; Milani, M. Chem. Eur. J. 2010, 16, 4368-4380.
35. (b) Caltagirone, C.; Hiscock, J.R.; Hursthouse, M.B.; Light, M.E.; Gale, P.A. Chem. Eur. J. 2008, 14, 10236-10243.
36. (c) Jose, D.A.; Singh, A.; Das, A.; Ganguly, B. Tetrahedron Lett. 2007, 48, 3695-3698.
37. (d) Kato, R.; Nishizawa, S.; Teramae, N. Chem. Commun. 2000, 755-756.
38. Sessler, J.L.; Katayev, E.; Pantos, G.D.; Scherbakov, P.; Reshetova, M.D.; Khrustalev, V.; Lynch, V.M.; Ustynyuk, Y.A.J. Am. Chem. Soc. 2005, 127, 11442-11446.
39. (a) Imabeppu, F.; Katagiri, K.; Masu, H.; Kato, T.; Tominaga, M.; therrien, B.; Takayanagi, H.; Kaji, E.; Yamaguchi, K.; Azumaya, I. Tetrahedron Lett. 2006, 47, 413-416.
40. (b) Azumaya, I; Okamoto, T.; Imabeppu, F.; Takayanagi, H. Tetrahedron 2003, 59, 2325-2331.
41. (c) Azumaya, I.; Kagechika, H.; Yamaguchi, K.; Shudo, K. Tetrahedron Lett. 1996, 37, 5003-5006.
42. (a) Fielding, L. Tetrahedron 2000, 56, 6151-6170.
43. (b) Gil, V.M.S.; Olivia, N.C. J. Chem. Ed. 1990, 67, 473-478.
44. (c) MacCarthy, P. Analytical Chemistry 1978, 50, 2165.
45. (d) Vosburgh, W.C.; Cooper, G.R. J. Am. Chem. Soc. 1941, 63, 437-442.
46. (a) Lee, D.H.; Im, J.H.; Lee, J.H.; Hong, J.I. Tetrahedron Lett. 2002, 43, 9637-9640.
47. (b) Kondo, S.; Nagamine, M.; Yano, Y. Tetrahedron Lett. 2003, 44, 8801-8804.
48. A short history of SHELX. Sheldrick, G.M. Acta Crystallogr. 2008, A64, 112-122.