Bio-inspired Calix[6]Arene-Zinc Funnel Complexes

Supramolecular Chemistry

Volumn 15, Issue 7-8, 2003, Pages 573-580

  Sénèque, Olivier ^a   Giorgi, Michel ^b   Reinaud, Olivia ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b Inst Mediterraneen d'Ecologie P   (France)

Author keywords

Biomimetic; Calixarene; Coordination; Host guest; N3 ligand; Zinc

Indexed keywords

CALIX[6]ARENE; CALIXARENE; IMIDAZOLE DERIVATIVE; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; ZINC ION;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; HYDROGEN BOND; HYDROPHOBICITY; PHYSICAL CHEMISTRY; SUPRAMOLECULAR CHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0242425696     PISSN: 10610278     EISSN: None     Source Type: Journal    
DOI: 10.1080/10610270310001605160     Document Type: Article

References (37)

1. Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417.
2. Reviews of molecular recognition: Chem. Rev. 1997, 97, 1232.
3. Diederich, F. Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1994.
4. Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. Engl. 1999, 28, 2978.
5. Lehn, J. M. Supramolecular Chemistry; VCH: Weinheim, 1995.
6. Cram, D. J.; Cram, J. M. Container Molecules and Their Guests, Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1994.
7. Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997.
8. Reviews of cyclodextrins: Chem. Rev. 1998, 98, 1741.
9. Collet, A. Tetrahedron 1987, 43, 5725.
10. Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239.
11. Castellano, R. K.; Nuckolls, C.; Rebek, Jr; J, J. Am. Chem. Soc. 1999, 121, 11156.
12. Rivera, J. M.; Martín, T.; Rebek, J. Jr. J. Am. Chem. Soc. 2001, 123, 5213.
13. Ikeda, A.; Udzu, H.; Zhong, Z.; Shinkai, S.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 2001, 123, 3872.
14. Gutsche, C. D. Calixarenes, Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1989.
15. Gutsche, C. D. Calixarenes Revisited, Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1998.
16. Arduini, A.; Secchi, A.; Pochini, A. J. Org. Chem. 2000, 65, 9085.
17. Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J. Calixarenes 2001; Kluwer Academic: Dordrecht, 2001.
18. Blanchard, S.; Le Clainche, L.; Rager, M.-N.; Chansou, B.; Tuchagues, J.-P.; Duprat, A. F.; Le Mest, Y.; Reinaud, O. Angew. Chem. Int., Ed. Engl. 1998, 37, 2732.
19. Sénèque, O.; Rager, M.-N.; Giorgi, M.; Reinaud, O. J. Am. Chem. Soc. 2000, 122, 6183.
20. Sénèque, O.; Rondelez, Y.; Le Clainche, L.; Inisan, C.; Rager, M.-N.; Giorgi, M.; Reinaud, O. Eur. J. Inorg. Chem. 2001, 2597.
21. Sénèque, O.; Rager, M.-N.; Giorgi, M.; Reinaud, O. J. Am. Chem. Soc. 2001, 123, 8442.
22. Sénèque, O.; Giorgi, M.; Reinaud, O. J. Chem. Soc., Chem. Commun. 2001, 984.
23. Müller, B.; Schneider, A.; Tesmer, M.; Vahrenkamp, H. Inorg. Chem. 1999, 38, 1900.
24. Blanchard, S.; Rager, M.-N.; Duprat, A.-F.; Reinaud, O. New J. Chem. 1998, 1143.
25. Rondelez, Y.; Sénèque, O.; Rager, M.-N.; Duprat, A.-F.; Reinaud, O. Chem. Eur. J. 2000, 6, 4218.
26. c was below 293 K.
27. 2 designate protons of aromatic rings bearing imidazole and methyl groups, respectively.
28. This corresponds to an estimated de of 20% for the process of chirality transmission, which is significant for standards of host-guest chemistry, especially for a non-optimized cavity filling [10-13].
29. We cannot yet determine which one of the two helical form is favoured by (S)-(-)-2-methylbutylamine.
30. Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8865.
31. Lipscomb, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375.
32. Håkansson, K.; Carlsson, M.; Svensson, L. A.; Liljas, A. J. Mol. Biol. 1992, 227, 1192.
33. Li, H.; Hallows, W. H.; Punzi, J. S.; Pankiewicz, K. W.; Watanabe, K. A. ; Goldstein, B. M. Biochemistry 1994, 33, 11734.
34. Al-Karadaghi, S.; Cedergren-Zeppezauer, E.; Hövmoller, S.; Petratos, K.; Terry, H.; Wilson, K. S. Acta Crystallogr. 1994, D50, 793.
35. Cho, H.; Ramaswamy, S.; Plapp, B. V. Biochemistry 1997, 36, 382.
36. Brüker Nonius, B.V.; Röntgenweg, 1, 2624 BD Delft, PO Box 811, 2600 Av Delft, The Netherlands.
37. Sheldrick, G. M. SHELXL97; University of Göttingen, Göttingen, Germany, 1997.