Nmr detection of simultaneous formation of [2]- and [3]pseudorotaxanes in aqueous solution between α-cyclodextrin and linear aliphatic α,ω-amino acids, an α,ω-diamine and an α,ω-diacid of similar length, and comparison with the solid-state structures

Journal of Organic Chemistry

Volumn 64, Issue 17, 1999, Pages 6217-6226

  Eliadou, Kyriaki ^a   Yannakopoulou, Konstantina ^a   Rontoyianni, Aliki ^a   Mavridis, Irene M ^a  

^a INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALPHA CYCLODEXTRIN; AMINE; AMINO ACID DERIVATIVE; MACROCYCLIC COMPOUND; PSEUDOROTAXANE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; DIPOLE; EQUILIBRIUM CONSTANT; PH; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STOICHIOMETRY; TEMPERATURE;

EID: 0033588139     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990021f     Document Type: Article

References (39)

1. (a) Harada, A.; Kamachi, M. Macromolecules 1990, 23, 2821-2823.
2. (b) Steinbrunn, M. B.; Wenz, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2139-2141.
3. (c) Wenz, G.; Keller, B. Angew. Chem., Int. Ed. Engl. 1992, 31, 197-199.
4. For the general idea, see (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2824. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401. (c) Makedonopoulou, S.; Mavridis, I. M.; Yannakopoulou, K.; Papaioanou, I. J. Chem. Soc., Chem. Commun. 1998, 2133-2134. (d) Harada, A.; Nishiyama, T.; Kawaguchi, Y.; Okada, M.; Kamachi, M. Macromolecules 1997, 30, 7115-7118.
5. For the general idea, see (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2824. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401. (c) Makedonopoulou, S.; Mavridis, I. M.; Yannakopoulou, K.; Papaioanou, I. J. Chem. Soc., Chem. Commun. 1998, 2133-2134. (d) Harada, A.; Nishiyama, T.; Kawaguchi, Y.; Okada, M.; Kamachi, M. Macromolecules 1997, 30, 7115-7118.
6. For the general idea, see (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2824. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401. (c) Makedonopoulou, S.; Mavridis, I. M.; Yannakopoulou, K.; Papaioanou, I. J. Chem. Soc., Chem. Commun. 1998, 2133-2134. (d) Harada, A.; Nishiyama, T.; Kawaguchi, Y.; Okada, M.; Kamachi, M. Macromolecules 1997, 30, 7115-7118.
7. For the general idea, see (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2824. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401. (c) Makedonopoulou, S.; Mavridis, I. M.; Yannakopoulou, K.; Papaioanou, I. J. Chem. Soc., Chem. Commun. 1998, 2133-2134. (d) Harada, A.; Nishiyama, T.; Kawaguchi, Y.; Okada, M.; Kamachi, M. Macromolecules 1997, 30, 7115-7118.
8. (a) Raymo, F. M.; Stoddart, J. F. Trends Polym. Sci. 1996, 4, 208-211.
9. (b) Ashton, P. R.; Philp, D.; Spencer, N.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1991, 1677-1679.
10. (a) Isnin, R.; Salam, C.; Kaifer, A. E. J. Org. Chem. 1991, 56, 35-41.
11. (b) Harada, A.; Li, J.; Kamachi, M. Macromolecules 1994, 27, 4538-4543.
12. (c) Toki, A.; Yonemura, H.; Matsuo, T. Bull. Chem. Soc. Jpn. 1993, 66, 3382-3386.
13. (a) Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1959-1976.
14. (b) Harada, A.; Li, J.; Kamachi, M. J. Am. Chem. Soc. 1994, 116, 3192-3196.
15. (c) Ogino, H. New J. Chem. 1993, 17, 683-688.
16. (d) Isnin, R.; Kaifer, A. E. J. Am. Chem. Soc. 1991, 113, 8188-8190.
17. (e) Isnin, R.; Kaifer, A. E. Pure Appl. Chem. 1993, 65, 495-497.
18. (f) Horsky, J. Eur. Polym. J. 1998, 34, 591-596.
19. Castronouvo, G.; Elia, V.; Fessas, D.; Giordano, A.; Velleca, F. Carbohydr. Res. 1995, 272, 31-39.
20. Rontoyianni, A.; Mavridis, I. M. Supramol. Chem., 1999, 10, 213-218.
21. Watanabe, M.; Nakamura, H.; Matsuo, T. Bull. Chem. Soc. Jpn. 1992, 65, 164-169.
22. Makedonopoulou, S.; Tulinsky, A.; Mavridis, I. M. Supramol. Chem., in press.
23. (a) Connors, K. A. Binding Constants. The Measurement of Molecular Complex Stability; John Wiley & Sons: New York, 1987.
24. (b) Chriswell, C. D.; Schilt, A. A. Anal. Chem. 1975, 47, 1623-1629.
25. The molecules were created with ChemDraw or Chem3D and minimized with the MM2 routine provided by CS Chem3D Pro (ChemOffice, CambridgeSoft).
26. c is the approximate coalescence temperature. The corresponding values for the energies of activation are ΔG‡ =15.3 kcal/mol, ΔG‡ =15.0 kcal/mol, and ΔG‡ = 15.1 kcal/mol, respectively, calculated using the approximate Eyring equation (Günther, H. NMR Spectroscopy-An Introduction; J. Wiley: New York, 1987; Chapter VIII) for the exchanging species.
27. a of aCD is 12.332 (Szejtli, J. Chem. Rev. 1998, 1743-1753).
28. Djedaïni, F.; Perly, B. Nuclear Magnetic Resonance of Cyclodextrins, Derivatives, and Inclusion Compounds. In New trends in Cyclodextrins and Derivatives; Duchêne, D., Ed.; Editions de Santé: Paris, France, 1991.
29. 2O (without deuterium lock) with and without the amino acid guests present revealed an alteration of its very broad hydroxyl peaks, indicating that hydrogen bonding of the host plays a role in the assembly of the pseudorotaxanes. More details, however, could not be extracted from these spectra.
30. Harada, A.; Li, J.; Kamachi, M.; Kitagawa, Y.; Katsube, Y. Carbohydr. Res. 1998, 305, 127-129.
31. Botsi, A.; Yannakopoulou, K.; Perly, B.; Hadjoudis, E. J. Org. Chem. 1995, 60, 4017-4023.
32. Ross, P. D.; Rekharsky, M. V. Biophys. J. 1996, 71, 2144-2154.
33. -3.
34. Mentzafos, D.; Mavridis, I. M.; LeBas, G.; Tsoucaris, G. Acta Crystallogr. 1991, B47, 746-57.
35. Aigouy, P. T.; Costeseque, P.; Sempere, R.; Senac, T. Acta Crystallogr. 1995, B51, 55-61.
36. Egert E.; Sheldrick, G. M. Acta Crystallogr. 1985, A41, 262.
37. Noltemeyer, M.; Saenger, W. J. Am. Chem. Soc. 1980, 102, 2710-2722.
38. Sheldrick, G. M. SHELXL93. Program for the Refinement of Crystal Structures, University of Göttingen, Germany.
39. Jones, T. A.; Kjeldgaad, M. Molecular Modelling Program; "O", Version 5.9, Upsala, Sweden, 1992.