Calix[4]arene-based receptors with hydrogen-bonding groups immersed into a large cavity

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9644-9651

  Pinkhassik, Evgueni ^a   Sidorov, Vladimir ^a   Stibor, Ivan ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ADAMANTANE DERIVATIVE; AMIDE; AMINE; CALIXARENE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; HYDROGEN BOND; MOLECULAR RECOGNITION; RECEPTOR BINDING;

EID: 0032567516     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9804543     Document Type: Article

References (42)

1. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures', Springer: Berlin, 1991.
2. (a) Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Oxford University Press: Oxford, 1991; Vol. 4.
3. (b) Hamilton, A. D. InAdvances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI Press Inc.: London, 1990; Vol. 1, pp 1-64.
4. van Doom, A. R.; Verboom, W.; Reinhoudt, D. N. InAdvances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI Press Inc.: London, 1993; Vol. 3, pp 169-206.
5. (a) Gutsche, C. D. Calixarenes. Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1989; Vol. 1.
6. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vincens, J., Boehmer, V., Eds.; Kluwer Academic: Dordrecht, 1991.
7. Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vogtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 2, pp 103-142.
8. Solid-state complexes are treated in the following: (a) Andreetti, G. D.; Ugozzoli, F. In Calixarenes: A Versatile Class of Macrocyclic Compounds; Vincens, J., Boehmer, V., Eds.; Kluwer Academic: Dordrecht, pp 87-123.
9. (b) Brouwer, E. B.; Ripmeester, J. A.; Enright, G. D. J. Incl. Phenom. 1996, 24, 1-17. Complexes in apolar media are regarded in the following:
10. Arduini, A.; McGregor, W. A.; Paganuzzi, D.; Pochini, A.; Secchi, A.; Ugozzoli, F.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1996, 839-846.
11. Kousaku, Y.; Yoshimasa, F. Tetrahedron Lett. 1996, 37, 1435-1438.
12. (e) Smirnov, S.; Sidorov, V.; Pinkhassik, E.; Havlíček, J.; Stibor, I. Supramol. Chem. 1997, 8, 187-196.
13. (f) Smirnov, S.; Sidorov, V.; Pinkhassik, E.; Koča, J.; Stibor, I. Supramol. Chem., in press.
14. (g) Sidorov, V.; Pinkhassik, E.; Smirnov, S.; Stibor, I.; Kovalev, V.; Khomich, A.; Shokova, E. Supramol. Chem., in press.
15. (a) van Loon, J. P.; Heida, J. F.; Verboom, W.; Reinhoudt, D. N. Reel. Trav. Chim. Pays-Bas 1992, 111, 353.
16. (b) Murakami, H.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1993, 1533.
17. van Loon, J.-D.; Janssen, R. G.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1992, 33, 5125.
18. (a) Iwamoto, K.; Araki, K; Shinkai, S. J. Org. Chem. 1991, 56, 4955.
19. (b) Groenen, L. C.; Steinwender, E.; Lutz, B. T. G.; van der Maas, J. H.; Rcinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1992, 1893.
20. Ikeda, A.; Tsuzuki, H.; Shinkai, S. J. Chem Soc., Perkin Trans. 2 1994, 2073.
21. Arduini, A.; Fabbi, M.; Mantovani, M.; Mirone, L.; Pochini, A.; Secchi, A.; Ungaro, R. J. Org. Chem. 1995, 60, 1454.
22. Kovalev, V.; Shokova, E.; Khomich, A.; Luzikov, Y. New J. Chem. 1996, 20, 483 and references therein.
23. Hunter, C. A. Chem. Soc. Rev. 1994, 101.
24. Krimer, L. I.; Cota, D. J. In Organic Reactions, 17; John Wiley & Sons: 1969; pp 213-325.
25. Khomich, A.; Shokova, E.; Kovalev, V. Synlett 1994, 1027.
26. (a) Burley, S. K.; Petsko, G. A. Science 1985, 229, 23.
27. (b) Diederich, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 362.
28. 13
29. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
30. Gutsche, C. D.; Pagpria, P. F. J. Org. Chem. 1985, 50, 5795.
31. Arduini, A.; Pochini, A.; Sicuri, A. R.; Secchi, A.; Ungaro, R. Gazz. Chim. Ital. 1994, 124, 129.
32. van Loon, J.-D.; Verboom, W.; Reinhoudt, D. N. Org. Prep. Proced. Int. 1992, 24, 437.
33. Connors, K. A. Binding Constants; Wiley & Sons: New York, 1987; p 410.
34. Diederich, F. In Cydophanes, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; ESC: Cambridge 1991; Vol. 3, p 82.
35. For several other receptors capable of tetrahedral recognition of water, see: (a) Chand, D. K; Ragunathan, K G.; Mak, T. C. W.; Bharadwaj, P. K. J. Org. Chem. 1996,61,1169.
36. (b) Dixon, D. A.; Dobbs, K. D. J. Phys. Chem. 1994, 98, 13435.
37. Timmerman, P.; Boerrigter, H.; Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1995, 114, 103.
38. The detailed description of the titration method and supplementary software is available at our address upon request.
39. Purchased from Aldrich Chemical Co.
40. Derome, A. Modern NMR Technique for Chemical Research; Organic Chemistry Series, 6; Pergamon Press: New York, 1987.
41. (a) Kreutzberger, A.; Schröders, H. H. Tetrahedron Lett. 1970, 4523.
42. (b) Isaev, S. D.; Novoselov, E. F.; Yurchenko, A. G. Zh. Org. Khim. 1985, 21, 114.