Structural evidence for an independent inclusion of hexyl and octyl chains of hexyldimethyloctylammonium bromide in an α-cyclodextrin cavity

Bulletin of the Chemical Society of Japan

Volumn 77, Issue 12, 2004, Pages 2165-2171

  Funasaki, Noriaki ^a   Yamauchi, Koji ^a   Ishikawa, Seiji ^a   Hirota, Shun ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; SUPRAMOLECULAR CHEMISTRY;

CHEMICAL SHIFT; INTERMOLECULAR CROSS-PEAKS; MACROSCOPIC BINDING; NONCOVALENT INTERACTIONS; OCTYL GROUPS;

AMMONIUM COMPOUNDS;

ALPHA CYCLODEXTRIN; HEXYLTRIMETHYLAMMONIUM; N,N,N HEXYLDIMETHYLOCTYLAMMONIUM BROMIDE; N,N,N TRIMETHYLOCTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; SUPRAMOLECULAR CHEMISTRY;

EID: 11144338178     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.77.2165     Document Type: Article

References (29)

1. M. L. Bender and M. Komiyama, "Cyclodextrin Chemistry." Springer-Verlag, Berlin (1978), Chaps. 2 and 3.
2. É. Fenyvesi, L. Szente, N. R. Russell, and M. McNamara, "Cyclodextrins," ed by J. Szejtli and T. Osa, Pergamon, London (1996). Chap. 10.
3. A. E. Kaifer, Adv. Supramol. Chem., 2, 1 (1992).
4. N. Funasaki, H. Yodo, S. Hada, and S. Neya, Bull. Chem. Soc. Jpn., 65, 1323 (1992).
5. W. M. Z. Wan Yunus, J. Taylor, D. M. Bloor, D. G. Hall, and E. Wyn-Jones, J. Phys. Chem., 96, 8979 (1992).
6. N. Funasaki, M. Ohigashi, S. Hada, and S. Neya, Langmuir, 16, 383 (2000), and references therein.
7. G. Gonźalez-Gaitano, A. Crespo, A. Compostizo, and G. Tardajos, J. Phys. Chem., 101, 4413 (1997).
8. N. Funasaki, S. Ishikawa, and S. Neya, J. Phys. Chem. B, 107, 10094 (2003).
9. H.-J. Schneider, F. Hacket, V. Rüdiger, and H. Ikeda, Chem. Rev., 98, 1755 (1998).
10. N. Funasaki, S. Ishikawa, and S. Neya, J. Phys. Chem. B, 106, 6431 (2002).
11. S. Ishikawa, S. Neya, and N. Funasaki, J. Phys. Chem. B, 102, 2502 (1998).
12. N. Funasaki, S. Ishikawa, and S. Neya, Langmuir, 18, 1786 (2002).
13. N. Funasaki, S. Ishikawa, and S. Neya, Langmuir, 16, 5584 (2000).
14. Y. Ohtani, T. Irie, K. Uekama, K. Fukunaga, and J. Petha, Eur. J. Biochem., 186, 17 (1989).
15. K. Yamoka, "Pharmacokinetic Analysis with Personal Computers," Nankoudou, Tokyo (1984), Chap. 4. This Basic version of "Multi" was translated into a Visual Basic version by us.
16. The cmc of dioctyldimethylammonium bromide is 22.2 (surface tension) and 23.0 (electric conductivity) mM.17 From the relationship between cmc and alkyl chain length for dialkyl-dimethylammonium bromides, that of HDOAB is expected to be 90 mM.17
17. K. Hiramatsu, K. Kameyama, R. Ishiguro, M. Mori, and H. Hayase, Bull. Chem. Soc. Jpn., 76, 1903 (2003).
18. M. V. Rekharsky, M. P. Mayhew, R. N. Goldberg, P. D. Ross, Y. Yamashoji, and Y. Inoue, J. Phys. Chem. B, 101, 87 (1997).
19. J. A. Pople, W. G. Schneider, and H. Bernstein, "High-Resolution Nuclear Magnetic Resonance," McGraw-Hill, New York (1959), Chap. 4 and Appendix C.
20. N. Funasaki, M. Nomura, H. Yamaguchi, S. Ishikawa, and S. Neya, Bull. Chem. Soc. Jpn., 73, 2727 (2000).
21. N. Funasaki, M. Nomura, S. Ishikawa, and S. Neya, J. Phys. Chem. B, 105, 7361 (2001).
22. N. Funasaki, H. Yamaguchi, S. Ishikawa, and S. Neya, J. Phys. Chem. B, 105, 760 (2001).
23. N. Funasaki, H. Yamaguchi, S. Ishikawa, and S. Neya, Bull. Chem. Soc. Jpn., 76, 903 (2003).
24. N. Funasaki and S. Hada, J. Colloid Interface Sci., 64, 454 (1978).
25. N. Funasaki, S. Hada, S. Neya, and K. Machida, J. Phys. Chem., 88, 5786 (1984).
26. S. Ishikawa, S. Hada, and N. Funasaki, J. Phys. Chem., 99, 11508 (1995).
27. S. Nepogodiev and J. F. Stoddart, Chem. Rev., 98, 1959 (1998).
28. M.-J. Lehn, "Supramolecular Chemistry," VCH Verlag, Berlin (1995).
29. J. J. Lundquist and E. J. Toone, Chem. Rev., 102, 555 (2002).