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Synthesis of stereoisomers of p-tert-butylthiacalix[4]arenes tetrasubstituted at the lower rim containing secondary amide groups and their complexation with a number of singly charged anions

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Abstract

The ability of new synthetic receptors, i.e., p-tert-butylthiacalix[4]arenes tetrasubstituted at the lower rim and containing secondary amide groups to form complexes with a number of spherical (F, Cl, Br, I), Y-shaped (MeCOO), trigonal (NO3 ), and tetrahedral (H2POO4 ) anions has been studied. It was shown that the nature of substituents on the nitrogen atom of the amide groups and configuration of the macrocycle affect the stability constant values of the forming complexes.

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References

  1. L. Baldini, Chem. Soc. Rev., 2007, 36, 254.

    Article  CAS  Google Scholar 

  2. J.-M. Lehn, Proc. Nat. Acad. Sci., 2002, 99, 4763.

    Article  CAS  Google Scholar 

  3. S. Mangani, M. Ferraroni, in Supramolecular Chemistry of Anions, Eds A. Bianchi, K. Bowman-James, K. Garcia-Espana, E. Garcia-Espana, Wiley-VCH, New York, 1997, 451 pp.

    Google Scholar 

  4. N. I. Kapranov, Gastroenterologiya Sankt-Peterburga [Gastroenterology of St. Petersburg], 2002, 4, 11 (in Russian).

    Google Scholar 

  5. I. Stibor, Anion Sensing, Springer Verlag, Berlin-Heidelberg, 2005, 233 pp.

    Google Scholar 

  6. P. A. Gale, Coord. Chem. Rev., 2001, 213, 79.

    Article  CAS  Google Scholar 

  7. S. Haner, J. Inc. Phen. Macr. Chem., 2006, 55, 151.

    Article  Google Scholar 

  8. R. Ungaro, N. Pelizzi, A. Casnati, A. Friggeri, J. Chem. Soc., Perkin Trans. 2, 1998, 1307.

  9. Y. Umezawa, S. Nishizawa, P. Buhlmann, M. Iwao, Tetrahedron Lett., 1995, 36, 6483.

    Article  Google Scholar 

  10. B. Tomapatanaget, T. Tuntulani, Tetrahedron Lett., 2001, 42, 8105.

    Article  CAS  Google Scholar 

  11. N. Morohashi, F. Narumi, N. Iki, T. Hattori, S. Miyano, Chem. Rev., 2006, 106, 5291.

    Article  CAS  Google Scholar 

  12. P. Lhotak, Eur. J. Org. Chem., 2004, 1675.

  13. D. Guo, Z. Liu, J. Ma, R. Huang, Tetrahedron Lett., 2007, 48, 1221.

    Article  CAS  Google Scholar 

  14. I. I. Stoikov, V. A. Smolentsev, I. S. Antipin, W. D. Habicher, M. Gruner, A. I. Konovalov, Mendeleev Commun., 2006, 16, 294.

    Article  Google Scholar 

  15. N. Iki, F. Narumi, T. Fujimoto, N. Morohashi, S. Miyano, J. Chem. Soc., Perkin Trans. 2, 1998, 2745.

  16. H. Becker, W. Berger, G. Domschke, E. Fanghanel, J. Faust, M. Fischer, F. Gentz, K. Gewald, R. Gluch, R. Mayer, K. Müller, D. Pavel, H. Schmidt, K. Schollberg, K. Schwetlick, E. Seiler, G. Zeppenfeld, Organikum. Organischchemisches Grundpraktikum, Veb Deutscher Verlag Der Wissenschaften, Berlin, 1974, vol. 2.

    Google Scholar 

  17. K. Hirose, J. Incl. Phenom. Macrocycl. Chem., 2001, 39, 193.

    Article  CAS  Google Scholar 

  18. J. Budka, P. Lhotak, V. Michlova, I. Stibor, Tetrahedron Lett., 2001, 42, 1583.

    Article  CAS  Google Scholar 

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Correspondence to I. I. Stoikov.

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Dedicated to Academician A. I. Konovalov in honor of his 75th anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 982–989, May, 2009.

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Zhukov, A.Y., Fink, T.A., Stoikov, I.I. et al. Synthesis of stereoisomers of p-tert-butylthiacalix[4]arenes tetrasubstituted at the lower rim containing secondary amide groups and their complexation with a number of singly charged anions. Russ Chem Bull 58, 1007–1014 (2009). https://doi.org/10.1007/s11172-009-0129-9

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  • DOI: https://doi.org/10.1007/s11172-009-0129-9

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