Tuning of the cavity of water-soluble thiacalix [4]arene for the control of inclusion ability toward water-miscible organic molecules

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 5, 2004, Pages 1080-1096

  Kon, Noriyoshi ^a   Iki, Nobuhiko ^a   Sano, Yuichiro ^a   Ogawa, Satoshi ^a   Kabuto, Chizuko ^a   Miyano, Sotaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alcohols; Calixarenes; Hydrophobic interactions; Inclusion; Ketones; Molecular recognition; NMR spectroscopy; Thiacalixarenes; X ray diffraction

Indexed keywords

ALCOHOL DERIVATIVE; ALIPHATIC COMPOUND; CALIXARENE; KETONE; NITRILE; ORGANIC COMPOUND; WATER;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; HYDROPHOBICITY; SOLUBILITY; STEREOCHEMISTRY;

EID: 3242763749     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20041080     Document Type: Article

References (32)

1. a) Kumagai H., Hasegawa M., Miyanari S., Sugawa Y., Sato Y., Hori T., Ueda S., Kamiyama H., Miyano S.: Tetrahedron Lett. 1997, 38, 3971;
2. b) Iki N., Kabuto C., Fukushima T., Kumagai H., Takeya H., Miyanari S., Miyashi T., Miyano S.: Tetrahedron 2000, 56, 1437;
3. c) Kon N., Iki N., Miyano S.: Tetrahedron Lett. 2002, 43, 2231.
4. Reviews: a) Iki N., Miyano S.: J. Chem. Soc. Jpn., Chem. Ind. Chem. 2001, 609; b) Iki N., Miyano S.: J. Inclusion Phenom. Macrocycl. Chem. 2001, 41, 99; c) Morohashi N., Iki N., Miyano S.: J. Synth. Org. Chem. Jpn. 2002, 60, 550.
5. Reviews: a) Iki N., Miyano S.: J. Chem. Soc. Jpn., Chem. Ind. Chem. 2001, 609; b) Iki N., Miyano S.: J. Inclusion Phenom. Macrocycl. Chem. 2001, 41, 99; c) Morohashi N., Iki N., Miyano S.: J. Synth. Org. Chem. Jpn. 2002, 60, 550.
6. Reviews: a) Iki N., Miyano S.: J. Chem. Soc. Jpn., Chem. Ind. Chem. 2001, 609; b) Iki N., Miyano S.: J. Inclusion Phenom. Macrocycl. Chem. 2001, 41, 99; c) Morohashi N., Iki N., Miyano S.: J. Synth. Org. Chem. Jpn. 2002, 60, 550.
7. a) Iki N., Morohashi N., Narumi F., Miyano S.: Bull. Chem. Soc. Jpn. 1998, 71, 1597;
8. b) Iki N., Morohashi N., Kabuto C., Miyano S.: Chem. Lett. 1999, 219;
9. c) Iki N., Morohashi N., Yamane Y., Miyano S.: Bull. Chem. Soc. Jpn. 2003, 76, 1763.
10. Iki N., Fujimoto T., Miyano S.: Chem. Lett. 1998, 625.
11. Kon N., Iki N., Miyano S.: Org. Biomol. Chem. 2003, 1, 751.
12. Iki N., Suzuki T., Koyama K., Kabuto C., Miyano S.: Org. Lett. 2002, 4, 509.
13. Iki N., Narumi F., Fujimoto T., Morohashi N., Miyano S.: J. Chem. Soc., Perkin Trans. 2 1998, 2745.
14. Iki N., Morohashi N., Narumi F., Fujimoto T., Suzuki T., Miyano S.: Tetrahedron Lett. 1999, 40, 7337.
15. a) Akdas H., Bringel L., Graf E., Hosseini M. W., Mislin G., Pansanel J., Cian A. D., Fischer J.: Tetrahedron Lett. 1998, 39, 2311;
16. b) Kabuto C., Higuchi Y., Niimi T., Hamada F., Iki N., Morohashi N., Miyano S.: J. Inclusion Phenom. Macrocycl. Chem. 2002, 42, 89.
17. Casnati A., Ting Y., Berti D., Fabbi M., Pochini A., Ungaro R., Sciotto D., Lombarde G. G.: Tetrahedron 1993, 49, 9815.
18. Matsumiya H., Terazono Y., Iki N., Miyano S.: J. Chem. Soc., Perkin Trans. 2 2002, 1166.
19. a) Doering W. von E., Schreiber K. C.: J. Am. Chem. Soc. 1955, 77, 514;
20. b) Doering W. von E., Hoffmann A. K.: J. Am. Chem. Soc. 1955, 77, 521.
21. a) Connors K. A.: Binding Constants. Wiley, New York 1987;
22. b) Fielding L.: Tetrahedron 2000, 56, 6151.
23. 1.
24. Leo A., Hansch C., Elkins D.: Chem. Rev. 1971, 71, 525.
25. Tanford C.: The Hydrophobic Effect, 2nd ed. Wiley-VCH, New York 1991.
26. a) Matsui Y., Mochida K.: Bull. Chem. Soc. Jpn. 1979, 52, 2808;
27. b) Poh B.-L., Tan C. M.: Tetrahedron 1993, 49, 9581;
28. c) Poh B.-L., Tan C. M.: J. Inclusion Phenom. Mol. Recogn. Chem. 1994, 18, 93;
29. d) Arena G., Contino A., Gulino F. G., Magri A., Sciotto D., Ungaro R.: Tetrahedron Lett. 2000, 41, 9327.
30. Smirnov S., Sidorov V., Pinkhassik E., Havlicek J., Stibor I: Supramol. Chem. 1997, 8, 187.
31. The distances between two para carbons of distally located phenolic unit are 7.15 Å for C10 to C22 and 9.86 A for C4 to C16.
32. Morohashi N., Katagiri H., Iki N., Yamane Y., Kabuto C., Hattori T., Miyano S.: J. Org. Chem. 2003, 68, 2324.