Synthesis of 6-Mono-6-deoxy-β-cyclodextrins Substituted with Isomeric Aminobenzoic Acids. Structural Characterization, Conformational Preferences, and Self-inclusion as Studied by NMR Spectroscopy in Aqueous Solution and by X-ray Crystallography in the Solid State

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8550-8557

  Eliadou, Kyriaki ^a   Giastas, Petros ^a   Yannakopoulou, Konstantina ^a   Mavridis, Irene M ^a  

^a INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS;

CONFORMATIONS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

AROMATIC HYDROCARBONS;

6 MONO 6 DEOXY BETA CYCLODEXTRIN DERIVATIVE; AMINOBENZOIC ACID DERIVATIVE; BETA CYCLODEXTRIN; CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; GLUCOSE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMISTRY; CONFORMATION; HYDROGEN BOND; ISOMER; ISOMERISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PURIFICATION; SOLID STATE; SOLUTION AND SOLUBILITY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINOBENZOIC ACIDS; BETA-CYCLODEXTRINS; CRYSTALLOGRAPHY, X-RAY; CYCLODEXTRINS; GLUCOSE; HYDROGEN BONDING; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PYRANS; SOLUTIONS; WATER;

EID: 0142258962     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034503+     Document Type: Article

References (36)

1. Wenz, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 803-822.
2. (a) Szejtli, J. Cyclodextrin Technology; Kluwer Academic Publishers: Dordrecht, 1988.
3. (b) Szejtli, J. Chem. Rev. 1998, 98, 1743.
4. Hedges, A. R. Chem. Rev. 1998, 98, 2035.
5. (a) Easton, C. J.; Lincoln, S. F. Modified Cyclodextrins - Scaffolds and Templates for Supramolecular Chemistry; Imperial College Press: London, 1999.
6. (b) Byun, H.; Zhong, N.; Bittman, R. Org. Synth. 1999, 77, 225.
7. (c) Brady, B.; Lynam, N.; O'Sullivan, T.; Ahern, C.; Darcy, R. Org. Synth. 1999, 77, 220.
8. (a) Ashton, P. R.; Koniger, R.; Stoddart, J. F. J. Org. Chem. 1996, 61, 903-908.
9. (b) Djedaini-Pilard, F.; Azaroual-Bellanger, N.; Gosnat, M.; Vernet, D.; Perly, B. J. Chem. Soc., Perkin Trans. 2 1995, 723.
10. (c) Ueno, A.; Ikeda, A.; Ikeda, H.; Ikeda, T.; Toda, F. J. Org. Chem. 1999, 64, 382.
11. (d) Hamasaki, K.; Ikeda, H.; Nakamura, A.; Ueno, A.; Toda, F.; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1993, 115, 5035.
12. (e) Vecchio, G.; La Mendola, D.; Rizzarelli, E.; J. Supramol. Chem. 2001, 1, 87.
13. (f) Ikeda, H.; Nakamura, M.; Ise, N.; Oguma, N.; Nakamura, A.; Ikeda, T. ; Toda, F.; Ueno, A. J. Am. Chem. Soc. 1996, 118, 10980.
14. (g) Kuwabara, T.; Nakamura, A.; Ueno, A.; Toda, F. J. Phys. Chem. 1994, 98, 6297.
15. (h) Péan, C.; Créminon, C.; Wijkhuisen, A.; Grassi, J.; Guenot, P.; Jéhan, P.; Dalbiez, J.-P.; Perly, B.; Djedaini-Pilard, F. J. Chem. Soc., Perkin Trans. 2 2000, 853.
16. (i) Schaschke, N.; Fiori, S.; Weyher, E.; Escrieut, C.; Fourmy, D.; Müller, G.; Moroder, L. J. Am. Chem. Soc. 1998, 120, 7030.
17. (a) Martin, K. A.; Czarnic, A. W. Tetrahedron Lett. 1994, 35, 6781.
18. (b) Yoon, J.; Hong, S.; Martin, K. A.; Czarnic, A. W. J. Org. Chem. 1995, 60, 2792.
19. (c) Huff, J. B.; Bieniarz, C. J. J. Org. Chem. 1994, 59, 7511.
20. (a) Liu, Y.; Han, B.-H.; Li, B.; Zhang, Y.-M.; Zhao, P.; Chen, Y.-T.; Wada, T.; Inoue, Y. J. Org. Chem. 1998, 63, 1444.
21. (b) Liu, Y.; Chen, Y.; Li, L.; Zhang, H.-Y. Supramol. Chem. 2002, 14, 299.
22. (c) Liu, Y.; You, C.-C.; Zhang, M.; Weng, L.-H.; Wada, T.; Inoue, Y. Org. Lett. 2000, 2, 2761.
23. (d) Liu, Y.; You, C.-C.; Kunieda, M.; Nakamura, A.; Wada, T.; Inoue, Y. Supramol. Chem. 2000, 12, 299.
24. (a) Corradini, R.; Dossena, A.; Galaverna, G.; Marchelli, R.; Panagia, A.; Sartor, G. J. Org. Chem. 1997, 62, 6283.
25. (b) Nakashima, H.; Takenaka, Y.; Higashi, M.; Yoshida, N. J. Chem. Soc., Perkin Trans. 2, 2001, 2096.
26. (c) Corradini, R.; Dossena, A.; Marchelli, R.; Panagia, A.; Sartor, G.; Saviano, M.; Lombardi, A.; Pavone, V. Chem. Eur. J. 1996, 2, 373.
27. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875 and references therein.
28. Schneider, H. J.; Hacket, F.; Rudiger, V. Chem. Rev. 1998, 98, 1755.
29. (a) Impellizzeri, G.; Papparaldo, G.; Rizzarelli, E.; Tringali, J. Chem. Soc., Perkin Trans. 2 1996, 1435.
30. (b) Matsushita, A.; Kuwabara, A.; Ikeda, H.; Ueno, A. J. Chem. Soc., Perkin Trans. 2 1997, 1705.;
31. (c) Liu, Y.; Fan, Z.; Zhang, H.-Y.; Diao, C.-H. Org. Lett. 2003, 5, 251.
32. Johnson, C. K. ORTEP, ORNL-5138. Oak Ridge National Laboratory: Oak Ridge, TN, 1973.
33. (a) Mentzafos, D.; Mavridis, I. M.; Le Bas, G.; Tsoucaris, G. Acta Crystallogr. 1991, B47, 746-757.
34. (b) Giastas, P.; Yannakopoulou, K.; Mavridis, I. M. Acta Crystallogr. 2003, B59, 287-299.
35. Harata, K.; Taenaka, Y.; Yoshida, N. J. Chem. Soc., Perkin Trans. 2 2001, 1667-1673.
36. Sheldrick, G. M. SHELXL97 Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.