Metal-ion extractability of sulfur-bridged oligomers of phenol; distinct effect of the number of sulfur bridges rather than the cyclic/acyclic form

Bulletin of the Chemical Society of Japan

Volumn 76, Issue 9, 2003, Pages 1763-1768

  Iki, Nobuhiko ^a   Morohashi, Naoya ^a,b   Yamane, Yusuke ^a   Miyano, Sotaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; OLIGOMERS; PH EFFECTS; PHENOLS;

EXTRACTABILITY;

SOLVENT EXTRACTION;

CALIXARENE; COBALT; COPPER; METAL ION; NICKEL; OLIGOMER; PHENOL DERIVATIVE; SULFUR DERIVATIVE; ZINC;

ACIDITY; CHEMICAL COMPOSITION; COMPLEX FORMATION; CONFERENCE PAPER; CYCLIZATION; MOLECULAR INTERACTION; STRUCTURE ANALYSIS;

EID: 0141817839     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.76.1763     Document Type: Conference Paper

References (48)

1. Part of this work was first presented at the 79th National Meeting of the Chemical Society of Japan (30 March, 2001, Kobe, Japan), Y. Yamane, N. Morohashi, N. Iki, K. Ito, Y. Ohba, and S. Miyano, Recognition Ability of Sulfur-Bridged Phenol Oligomers toward Metal Ions (3B106).
2. a) "Calixarenes for Separations," ACS Symposium Series 757, ed by G. J. Lumetta, R. D. Rogers, and A. S. Gopalan, American Chemical Society, Washington DC (2000).
3. b) R. Ludwig, Fresenius' J. Anal. Chem., 367, 103 (2000).
4. B. König and M. H. Fonseca, Eur. J. Inorg. Chem., 2000, 2303.
5. a) T. Sone, Y. Ohba, K. Moriya, and H. Kumada, "Abstract Book of Workshop on Calixarenes and Related Compounds," Fukuoka, Japan, 1993, PS/B-36.
6. b) T. Sone, Y. Ohba, K. Moriya, H. Kumada, and K. Ito, Tetrahedron, 53, 10689 (1997).
7. c) K. Ito, Y. Ohba, and T. Sone, Nippon Kagaku Kaishi, 1999, 217; Chem. Abstr., 130, 296617 (1999).
8. K. Ito, Y. Ohba, and T. Sone, Nippon Kagaku Kaishi, 1999, 217; Chem. Abstr., 130, 296617 (1999).
9. H. Kumagai, M. Hasegawa, S. Miyanari, Y. Sugawa, Y. Sato, T. Hori, S. Ueda, H. Kamiyama, and S. Miyano, Tetrahedron Lett., 38, 3971 (1997).
10. a) N. Iki and S. Miyano, Nippon Kagaku Kaishi, 2001, 609; Chem. Abstr., 136, 216664 (2001).
11. a) N. Iki and S. Miyano, Nippon Kagaku Kaishi, 2001, 609; Chem. Abstr., 136, 216664 (2001).
12. b) N. Iki and S. Miyano, J. Inclusion Phenom. Macrocyclic Chem., 41, 99 (2001).
13. c) N. Morohashi, N. Iki, and S. Miyano, J. Synth. Org. Chem., Jpn., 60, 550 (2002).
14. N. Iki, N. Morohashi, F. Narumi, and S. Miyano, Bull. Chem. Soc. Jpn., 71, 1597 (1998).
15. N. Morohashi, N. Iki, A. Sugawara, and S. Miyano, Tetrahedron, 57, 5557 (2001).
16. Izatt et al. reported selective transport of Cs+ ion through a liquid membrane containing p-tert-butylcalix [4]arene (1) and p-tert-pentylcalix[4]arene, which may be the only example to describe the use of p-alkylcalix[4]arene to partitioning of metal ions from aqueous into organic phase. a) R. M. Izatt, J. D. Lamb, R. T. Hawkins, P. R. Brown, S. R. Izatt, and J. J. Christensen, J. Am. Chem. Soc., 105, 1782 (1983).
17. b) S. R. Izatt, R. T. Hawkins, J. J. Christensen, and R. M. Izatt, J. Am. Chem. Soc., 107, 63 (1985).
18. a) N. Iki, N. Morohashi, C. Kabuto, and S. Miyano, Chem. Lett., 1999, 219.
19. b) A. Bilyk, A. K. Hall, J. M. Harrowfield, M. W. Hosseini, G. Mislin, B. W. Skelton, C. Taylor, and A. H. White, Eur. J. Inorg. Chem., 2000, 823.
20. c) G. Mislin, E. Graf, M. W. Hosseini, A. Bilyk, A. K. Hall, J. M. Harrowfield, B. W. Skelton, and A. H. White, Chem. Commun., 1999, 373.
21. d) A. Bilyk, A. K. Hall, J. M. Harrowfield, M. W. Hosseini, B. W. Skelton, and A. H. White, Inorg. Chem., 40, 672 (2001).
22. e) H. Akdas, E. Graf, M. W. Hosseini, A. De Cian, A. Bilyk, B. W. Skelton, G. A. Koutsantonis, I. Murray, J. M. Harrowfield, and A. H. White, Chem. Commun., 2002, 1042.
23. f) A. Bilyk, A. K. Hall, J. M. Harrowfield, M. W. Hosseini, B. W. Skelton, and A. H. White, Aust. J. Chem., 53, 895 (2000).
24. g) cf. H. Katagiri, N. Morohashi, N. Iki, C. Kabuto, and S. Miyano, Dalton Trans., 2003, 723.
25. - donor set, which has recently been exemplified by X-ray analysis of a Cu(II) complex. N. Morohashi, N. Iki, M. Aono, and S. Miyano, Chem. Lett., 2002, 494; T. Kajiwara, N. Kon, S. Yokozawa, T. Ito, N. Iki, and S. Miyano, J. Am. Chem. Soc., 124, 11274 (2002).
26. - donor set, which has recently been exemplified by X-ray analysis of a Cu(II) complex. N. Morohashi, N. Iki, M. Aono, and S. Miyano, Chem. Lett., 2002, 494; T. Kajiwara, N. Kon, S. Yokozawa, T. Ito, N. Iki, and S. Miyano, J. Am. Chem. Soc., 124, 11274 (2002).
27. Recently, Ohba and his coworkers communicated the results of the metal extraction by a series of related ligands at the 81st National Meeting of the Chemical Society of Japan (28 March, 2002, Tokyo, Japan), H. Teraura, D. Watanabe, T. Ito, Y. Hirano, K. Ito, and Y. Ohba, Preceedings of the Meeting, 3PB039.
28. -4 M, pH 6.1 with 0.05 M PIPES buffer. See also supplementary material.17
29. D. W. Margerum, G. R. Cayley, D. C. Weatherburn, and G. K. Pagenkopf, "Coordination Chemistry," Vol. 2, ed by A. E. Martell, American Chemical Society, Washington D. C. (1978), ACS monograph 174, p. 46.
30. 1/2, is defined as the pH where E% = 50%.
31. This may partly owe to the lower number (= 1) of the bound water to the Cu(II) center in the 1:1 complex with 5 because of Jahn-Teller effect.
32. Refer to supplementary materials (Deposited Document No. 03054).
33. a) R. G. Pearson, J. Am. Chem. Soc., 85, 3533 (1963).
34. b) R. G. Pearson, J. Chem. Educ., 45, 581 (1968).
35. a) J. H. Hildebaland, J. M. Prausnits, and R. L. Scott, "Regular and Related Solutions," Van Nostrand Reinhold Co., New York (1970).
36. b) T. Wakahayashi, S. Oki, T. Omori, and N. Suzuki, J. Inorg. Nucl. Chem., 26, 2255 (1964).
37. c) T. Omori, T. Wakahayashi, S. Oki, and N. Suzuki, J. Inorg. Nucl. Chem., 26, 2265 (1964).
38. d) I. Kojima, M. Uchida, and M. Tanaka, J. Inorg. Nucl. Chem., 32, 1333 (1970).
39. D,H4L.
40. C. D. Gutsche, "Calixarenes," Monographs in Supramolecular Chemistry, ed by J. F. Stoddart, The Royal Society of Chemistry, Cambridge (1989).
41. T. Cairns and G. Eglinton, Nature, 196, 535 (1962).
42. N. Iki, C. Kabuto, T. Fukushima, H. Kumagai, H. Takeya, S. Miyanari, T. Miyashi, and S. Miyano, Tetrahedron, 56, 1437 (2000).
43. H. Matsumiya, Y. Takahashi, N. Iki, and S. Miyano, J. Chem. Soc., Perkin Trans. 2, 2002, 1166.
44. J. E. Leffler and E. Gunwald, "Rates and Equilibria of Organic Reactions," John Wiley and Sons, Inc., New York (1963).
45. 2], the structure of which was characterized by X-ray analysis.
46. cf. It may be expected that 2,14-dithiacalix[4]arene (6) should have extractability via forming 2:2 double-cone structure similar to Scheme 5. In fact, it has been observed that 6 extracted transition metal ions, although the extractability was somewhat lower than that of tetrathia 2. N. Kon, N. Iki, Y. Yamane, S. Shirasaki, and S. Miyano, in preparation.
47. Y. Ohba, K. Moriya, and T. Sone, Bull. Chem. Soc. Jpn., 64, 576 (1991).
48. K. Ueno, "Chelatometry," Nankodo, Tokyo (1989).