Calix[4]arene-5,17-dicarboxylic acids and their interactions with aliphatic amines. Part 1. Studies in solution

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 9, 2000, Pages 1929-1934

  Jørgensen, Mikkel ^a   Krebs, Frederik C ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; AMINES; BINDING ENERGY; CONFORMATIONS; DIMERS; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTITUTION REACTIONS; TITRATION; X RAY CRYSTALLOGRAPHY;

ALIPHATIC AMINES; BINDING CONSTANTS; CALIXARENES; DICARBOXYLIC ACIDS;

CARBOXYLIC ACIDS;

EID: 0034286422     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002407o     Document Type: Article

References (35)

1. C. D. Gutsche and M. Iqbal, Org. Synth., 1990, 68, 234.
2. (a) C. D. Gutsche, Calixarenes: Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, Royal Society of Chemistry, London, 1989
3. (b) J. Vicens and V. Böhmer, Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht, 1990
4. (c) V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
5. K. Iwamoto, K. Fujimoto, T. Matsuda and S. Shinkani, Tetrahedron Lett., 1990, 31, 7169; see also ref. 2.
6. (a) M. Almi, A. Arduini, A. Casnati, A. Pochini and R. Ungaro, Tetrahedron, 1989, 45, 2177
7. (b) C. D. Gutsche and K. C. Nam, J. Am. Chem. Soc., 1988, 110, 6153
8. (c) S. Shinkai, T. Nagasaki, K. Iwamoto, A. Ikeda, G. X. He, T. Matsuda and M. Iwamoto, Bull. Chem. Soc. Jpn., 1991, 64, 381
9. (d) C. D. Gutsche and P. F. Pagoria, J. Org. Chem., 1985, 50, 5795
10. (e) S. Shinkai, K. Araki, T. Tsubaki, T. Arimura and O. Manabe, J. Chem. Soc., Perkin Trans. 1, 1987, 2297
11. (f) W. Verboom, A. Durie, R. J. M. Egberink, Z. Asfari and D. N. Reinhoudt, J. Org. Chem., 1992, 57, 1313.
12. (a) R. M. Izatt, J. D. Lamb, R. T. Hawkins, P. R. Brown, S. R. Izatt and J. J. Christensen, J. Am. Chem. Soc., 1983, 105, 1782
13. (b) G. Calestani, F. Ugozzoli, A. Arduini, E. Ghidini and R. Ungaro, J. Chem. Soc., Chem. Commun., 1987, 344
14. (c) E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A. A. El-Fadl and D. N. Reinhoudt, J. Am. Chem. Soc., 1990, 112, 6979.
15. (a) P. D. Beer, C. A. P. Dickson, N. Fletcher, A. J. Goulden, A. Grieve, J. Hodachova and T. Wear, J. Chem. Soc., Chem. Commun., 1993, 828
16. (b) D. M. Rudkievich, W. Verboon and D. N. Reinhoudt, J. Org. Chem., 1994, 59, 3683
17. (c) J. S. M. Fochi, J. F. J. Engbersen and D. N. Reinhoudt, J. Org. Chem., 1994, 59, 7815.
18. (a) G. D. Andreetti, R. Ungaro and A. Pochini, J. Chem. Soc., Chem Commun., 1979, 1005
19. (b) J.-D. van Loon, J. F. Heida, W. Verboom and D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas, 1992, 111, 353
20. (c) H. Murakami and S. Shinkani, J. Chem. Soc., Chem. Commun., 1993, 828
21. (d) C. D. Gutsche and K. A. See, J. Org. Chem., 1992, 57, 4527
22. (e) P. Timmerman, E. A. Brinks, W. Verboom and D. N. Reinhoudt, J. Chem. Soc., Chem. Commun., 1995, 417.
23. A. Arduini, M. Fabbi, M. Mantovani, L. Mirone, A. Pochini, A. Secchi and R. Ungaro, J. Org. Chem., 1995, 60, 1454.
24. P. D. J. Grootenhuis, P. A. Kollman, L. C. Groenen, D. N. Reinhoudt, G. J. van Hummel, F. Ugozzoli and G. D. Andreetti, J. Am. Chem. Soc., 1990, 112, 4165.
25. O. Struck, W. Verboom, W. J. J. Smeets, A. L. Spek and D. N. Reinhoudt, J. Chem. Soc., Perkin Trans. 2, 1997, 223.
26. (a) M. Jørgensen, M. Larsen, P. Sommer-Larsen, W. B. Petersen and H. Eggert, J. Chem. Soc., Perkin Trans. 1, 1997, 2851
27. (b) F. C. Krebs, M. Larsen, M. Jørgensen, P. R. Rasmussen, M. Bielecki and K. Schaumburg, J. Org. Chem., 1998, 63, 9872.
28. M. Larsen, F. C. Krebs, N. Harrit and M. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1999, 1749.
29. M. Larsen, F. C. Krebs, M. Jørgensen and N. Harrit, J. Org. Chem., 1998, 63, 4420.
30. F. C. Krebs and M. Jørgensen, following paper in this issue, DOI 10.1039/b002409k.
31. M. Larsen and M. Jørgensen, J. Org. Chem., 1996, 61, 6651.
32. Houben-Weyl, Methoden der Organische Chemie, Georg Thieme Verlag, Stuttgart, 1965, part 10/3, p. 332.
33. M. J. Hynes, J. Chem. Soc., Dalton Trans., 1993, 311.
34. P. G. Jones, D. Döering, T. Laue and H. Hopf, Acta Crystallogr., Sect. C, 1993, 49, 1192.
35. P. S. Bates, R. Kataky and D. Parker, J. Chem. Soc., Perkin Trans. 2, 1994, 669.