Design and Synthesis of New Chiral Calix[4]arenes as Liquid Phase Extraction Agents for α-Amino Acid Methylesters and Chiral α-Amines

Article

Abstract

The article describes the synthesis and extraction properties of new (S)-(-)-1-phenylethylamine substituted p-tert-butylcalix[4]arene/calix[4]arene. These compounds have been synthesized via nucleophilic substitution reactions involving 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra(2-hydroxyethoxy)calix[4]arene (4a), or 5,11,17,23-tetra-H-25,26,27,28-tetra(2-hydroxyethoxy)calix[4]arene (4b) with (S)-(-)-1-phenylethylamine in dry THF. The extraction properties of ligands 5a and 5b towards the some selected α-amino acid methylesters and chiral α-amines are also reported. It has been observed that receptor 5a was an excellent ionophore for α-amino acid methylesters/α-amines and good extractant than 5b. However, both of the ligands did not display any selectivity towards the configurations of this species.

Keywords

amino acid methylesters calixarene chiral separation extraction 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Gutsche, C.D. 1989Calixarenes, Monographs in Supramolecular ChemistryThe Royal Society of ChemistryCambridgeGoogle Scholar
  2. 2.
    Böhmer, V. 1995Angew. Chem., Int. Ed. Engl.34713Google Scholar
  3. 3.
    Buschmann, H.-J., Cleve, E., Jansen, K., Wego, A., Schollmeyer, E. 2001Mat. Sci. Eng. C143539CrossRefGoogle Scholar
  4. 4.
    Danilde Namor, A.F., Cleverley, R.M., Zapata-Ormachea, M.L. 1998Chem. Rev.9824952525CrossRefPubMedGoogle Scholar
  5. 5.
    Ikeda, A., Shinkai, S. 1997Chem. Rev9717131734CrossRefPubMedGoogle Scholar
  6. 6.
    Bartsch, R.A., Way, J.D. 1996Chemical Separations With Liquid MembranesACS Symposium SeriesWashingtonGoogle Scholar
  7. 7.
    Ediz, O., Tabakci, M., Memon, S., Yilmaz, M., Roundhill, D.M. 2004Supramol. Chem.1617CrossRefGoogle Scholar
  8. 8.
    Tabakci, M., Memon, S., Yilmaz, M., Roundhill, D.M. 2004J. Polym. Sci. Part A: Polym. Chem.42186193CrossRefGoogle Scholar
  9. 9.
    Tabakci, M., Memon, S., Yilmaz, M., Roundhill, D.M. 2003J Incl Phenom Macrocyclic Chem.45267270CrossRefGoogle Scholar
  10. 10.
    Demirel, A., Dogan, A., Canel, E., Memon, S., Yilmaz, M., Kilic, E. 2004Talanta62123129CrossRefGoogle Scholar
  11. 11.
    Alpoguz, H.K., Memon, S., Ersouml, M.Z., Yilmaz, M. 2004Sep. Sci. Tech39799810CrossRefGoogle Scholar
  12. 12.
    Izatt, S.R., Hawkins, R.T., Christensen, J.J., Izatt, R.M. 1985J. Am. Chem. Soc.1076366CrossRefGoogle Scholar
  13. 13.
    Stödeman, M., Dhar, N. 1998Thermochim. Acta3203338CrossRefGoogle Scholar
  14. 14.
    Arnaud-Neu, F., Schwing-Weill, M.-J. 1997Synthetic. Metals90157164CrossRefGoogle Scholar
  15. 15.
    Chrisstoffels, L.A.J., Struijk, W., Jong, F., Reinhoudt, D.N. 1996J. Chem. Soc. Perkin. Trans.216171622Google Scholar
  16. 16.
    Chang S.-K., Hwang H.-S., Son H., Youk J., Kang Y.S. (2000). J. Chem. Soc., Chem. Commun. 217–218Google Scholar
  17. 17.
    Schneider, H.-J., Eblinger, F., Sirish, M. 2000Adv. Supramol. Chem.6185216Google Scholar
  18. 18.
    Still, W.C. 1996Acc. Chem. Res.29155163CrossRefGoogle Scholar
  19. 19.
    Mandolini, L.Ungaro, R. eds. 2000Calixarenes in ActionImperial CollegeLondonGoogle Scholar
  20. 20.
    Asfari, Z.Böhmer, V.Harrowfield, J.Vicens, J. eds. 2001Calixarenes 2001Kluwer Academic PublishersDordrechtGoogle Scholar
  21. 21.
    Baklouti, L., Abidi, R., Asfari, Z., Harrowfield, J., Rokbani, R., Vicens, J. 1998Tetrahedron Lett.3953635366CrossRefGoogle Scholar
  22. 22.
    Arena, G., Contino, A., Gulino, FG., Magri, A., Sansone, F., Sciotto, D., Ungaro, R. 1999Tetrahedron Lett.4015971600CrossRefGoogle Scholar
  23. 23.
    Fraternali, F., Wipff, G. 1997An. Quim. Int. Ed.93376384Google Scholar
  24. 24.
    Mutihac, L., Buschmann, H.-J., Tuderoscu, A., Mutihac, R. 2003J. Incl. Phenom. Macrocyclic Chem.47123128CrossRefGoogle Scholar
  25. 25.
    Schneider, H.-J., Güttes, D., Schneider, U. 1988J. Am. Chem. Soc.11064496454CrossRefGoogle Scholar
  26. 26.
    Buschmann, H.-J., Mutihac, L., Jansen, K. 2001J. Incl. Phenom. Macrocyclic Chem.39111CrossRefGoogle Scholar
  27. 27.
    Araki, K., Inada, K., Shinkai, S. 1996Angew. Chem. Int. Ed. Engl.357274CrossRefGoogle Scholar
  28. 28.
    Kubo, Y., Maeda, SY., Tokita, S., Kubo, M. 1996Nature382522524CrossRefGoogle Scholar
  29. 29.
    Zhao, T., Hu, XJ., Chang, J., Lu, X. 1998Anal. Chim. Acta358263268CrossRefGoogle Scholar
  30. 30.
    Odashima, K., Yagi, K., Tohda, K., Umezawa, Y. 1993Anal. Chem.6510741083CrossRefGoogle Scholar
  31. 31.
    Chan, WH., Shiu, KK., Gu, X.H. 1993Analyst118863867CrossRefGoogle Scholar
  32. 32.
    Chen, LX., He, XW., Hu, XB., Xu, H. 1999Analyst.12417871790CrossRefGoogle Scholar
  33. 33.
    Kremer, F.JB., Chiosis, G., Engbersen, J.F.J., Reinhoudt, D.N. 1994J. Chem. Soc., Perkin Trans.2677681Google Scholar
  34. 34.
    Chang, SK., Son, HJ., Hwang, HS., Kang, Y.S. 1990Bull. Korean Chem. Soc.11364365Google Scholar
  35. 35.
    Zolotov, YA., Pletnev, IV., Torocheshnikova, II., Shvdene, NV., Nemilova, MY., Kovalev, VV., Shokova, EA., Smirnova, S.V. 1994Solv. Extr. Res. Dev. Jpn.1123Google Scholar
  36. 36.
    Wong, P.S.H., Yu, X., Dearden, D.V. 1996Inorg. Chim. Acta246259265CrossRefGoogle Scholar
  37. 37.
    Vincenti, M., Irico, A., Dalcanale, E. 1998Adv. Mass Spectrom.14129Google Scholar
  38. 38.
    Oshima, T., Goto, M., Furusaki, S. 2002J. Incl. Phenom. Macrocyclic Chem.437786CrossRefGoogle Scholar
  39. 39.
    Mutihac, L., Buschmann, H.-J., Diacu, E. 2002Desalination.148253256CrossRefGoogle Scholar
  40. 40.
    Okada, Y., Kasai, Y., Nishimura, J. 1995Tetrahedron Lett.36555558CrossRefGoogle Scholar
  41. 41.
    Gutsche, CD., Iqbal, M., Stewart, D. 1986J. Org. Chem.51742745CrossRefGoogle Scholar
  42. 42.
    Knoblauch, S., Falana, OM., Nam, J., Roundhill, DM., Henning, H., Zeckert, K. 2000Inorg. Chim. Acta.300328332CrossRefGoogle Scholar
  43. 43.
    Pedersen, C.J. 1968J. Fed. Proc. Fed. Am. Soc. Exp. Biol.271305Google Scholar

Copyright information

© Springer 2005

Authors and Affiliations

  • Mustafa Tabakci
    • 1
  • Begum Tabakci
    • 1
  • Mustafa Yilmaz
    • 1
  1. 1.Department of ChemistrySelçuk UniversityKonyaTurkey

Personalised recommendations