Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Ammonium Ion Binding Property of Naphtho-Crown Ethers Containing Thiazole as Sub-Cyclic Unit

  • Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University) ;
  • Do, Kyung-Soon (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Ki-Soo (Department of Applied Chemistry, Kyungpook National University) ;
  • Shim, Jun-Ho (Chemical Sensor Research Group, Department of Chemistry, Kwangwoon University) ;
  • Cha, Geun-Sig (Chemical Sensor Research Group, Department of Chemistry, Kwangwoon University) ;
  • Nam, Hak-Hyun (Chemical Sensor Research Group, Department of Chemistry, Kwangwoon University)
  • Published : 2004.10.20
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Abstract

A short and efficient synthesis, solvent extraction and potentiometric measurements of new thiazole-containing naphtho-crown ethers are reported. The naphthalene moiety enhances the ammonium ion selectivity over potassium ion. The selectivity of ${NH_4}^+/K^+$ follows the trend $3\;{\approx}\;2\;>\;1$, indicating that the differences in conformational changes of 2 and 3 in forming ammonium complexes affect little on the resulting ammonium/potassium extraction selectivity ratio. The ammonium ion-selective electrodes were prepared with noctylphenyl ether plasticized poly(vinyl chloride) membranes containing 1-4 the effect of one naphthalene unit introduced on either right (2) or left (3) side of thiazolo-crown ether on their potentiometric properties (e.g., ammonium ion selectivity over other cations, response slopes, and detection limits) were not apparent. However, the ammonium ion selectivity of 1, 2 and 3 over other alkali metal and alkaline earth metal cations is 10-100 times higher than that of nonactin.

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References

  1. Buhlman, P.; Pretch, E.; Bakker, E. Chem. Rev. 1998, 98, 1593. https://doi.org/10.1021/cr970113+
  2. Dobler, M. In Comprehensive Supramolecular Chemistry; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D.; Vögtle, F., Eds;Pergamon: Oxford, 1996; Vol. 1.
  3. Hall, E. A. H. Biosensors; Open University Press: Buckingham,U.K., 1990: chapter 9.
  4. Kim, H.-S.; Park, H. J.; Oh, H. J.; Koh, Y. K.; Choi, J.-H.; Lee, D.-H.; Cha, G. S.; Nam, H. Anal. Chem. 2000, 72, 4683. https://doi.org/10.1021/ac000177b
  5. Kariuki, B. M.; Lee, S.-O.; Harris, K. D. M.; Kim, H.-S.; Do, K.-S.; Kim, K.-I. Cryst. Growth & Design 2002, 2, 309. https://doi.org/10.1021/cg020008f
  6. Kim, H.-S.; Kim, D. H.; Kim, K. S.; Choi, H. J.; Shim, J. H.;Jeong, I. S.; Cha, G. S.; Nam, H. J. Inclusion Phenom. MacrocyclicChem. 2003, 46, 201. https://doi.org/10.1023/A:1026331014375
  7. Jin, H. Y.; Kim, T. H.; Kim, J.; Lee, S. S.; Kim, J. S. Bull. KoreanChem. Soc. 2004, 25, 59. https://doi.org/10.5012/bkcs.2004.25.1.059
  8. Campayo, L.; Pardo, M.; Cotillas, A.; Jaúregui, O.; Yunta, M.J. R.; Cano, C.; Gomez-Contreas, F.; Navarro, P.; Sanz, A. M.Tetrahedron 2004, 60, 979. https://doi.org/10.1016/j.tet.2003.11.040
  9. Navarro, P.; Rodriguez-Franco, M.I.; Foces-Foces, C.; Cano, F.; Samat, A. J. Org. Chem. 1989, 54,1391. https://doi.org/10.1021/jo00267a030
  10. Benco, J. S.; Nienaber, H. A.; McGimpsey, W. G. Anal. Chem.2003, 75, 152. https://doi.org/10.1021/ac0257851
  11. Sasaki, S.; Amano, T.; Monma, G.; Otsuka, T.; Iwasawa, N.;Citterio, D.; Hisamoto, H.; Suzuki, K. Anal. Chem. 2002, 74,4845. https://doi.org/10.1021/ac025713+
  12. Suzuki, K.; Siswanta, D.; Otsuka, T.; Amano, T.; Ikeda,T.; Hisamoto, H.; Yoshihara, R.; Ohba, S. Anal. Chem. 2000, 72,2200. https://doi.org/10.1021/ac9911241
  13. Chin, J.; Oh, J.; Jon, S. Y.; Park, S. H.; Walsdorff, C.;Stranix, B.; Ghoussoub, A.; Lee, S. J.; Chung, H. J.; Park, S.-M.;Kim, K. J. Am. Chem. Soc. 2002, 124, 5374. https://doi.org/10.1021/ja0174175
  14. Ahn, K. H.; Kim, S.-G.; Jung, J.; Kim, K.-H.; Chin, J.; Kim, K. Chem. Lett. 2000, 170.
  15. Chin, J.; Oh, J.; Walsdorff, C.; Stranix, B.; Oh, J.;Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem. Int. Ed. 1999,38, 2756. https://doi.org/10.1002/(SICI)1521-3773(19990917)38:18<2756::AID-ANIE2756>3.0.CO;2-6
  16. Graf, E.; Kintzinger, J. P.; Lehn, J. M.; LeMoigne, J. J. Am. Chem.Soc. 1982, 104, 1672. https://doi.org/10.1021/ja00370a037
  17. Kim, H.-S.; Koh, Y. K.; Choi, J. H. J. Hetrocyclic Chem. 1998,35, 177. https://doi.org/10.1002/jhet.5570350134
  18. Choi, J.-H.; Koh, Y. K.; Kwon, I.-C.; Kim, H.-S.;Park, H. J.; Kim, S. J.; Cha, G. S.; Nam, H. Bull. Korean Chem.Soc. 1999, 20, 581.
  19. Ouchi, M.; Inoue, Y.; Sakamoto, H.; Yamahira, A.; Yoshinaga,M.; Hakushi, T. J. Org. Chem. 1983, 48, 3168. https://doi.org/10.1021/jo00167a007
  20. Nolte, R. J. M.; Cram, D. J. J. Am. Chem. Soc. 1984, 106, 1416. https://doi.org/10.1021/ja00317a037
  21. Ouchi, M.; Inoue, Y.; Wada, K.; Iketani, S.-I.; Hakushi, T.; Weber,E. J. Org. Chem. 1987, 52, 2420. https://doi.org/10.1021/jo00388a016
  22. Oh, H. J.; Cha, G. S.; Nam, H. Bull. Korean Chem. Soc. 2003, 24,37. https://doi.org/10.1007/s11814-007-5006-3
  23. Gadzekpo, V. P. Y.; Christian, G. D. Anal. Chim. Acta 1984, 164,279. https://doi.org/10.1016/S0003-2670(00)85640-8
  24. Buck, R. P.; Lindner, E. Pure Appl. Chem. 1994, 66, 2527. https://doi.org/10.1351/pac199466122527
  25. Umezawa, Y.; Umezawa, K.; Sato, H. Pure Appl. Chem. 1995, 67,507. https://doi.org/10.1351/pac199567030507

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