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p-tert-butylcalix[4]arenes containing azacrown ether substituents at the lower rim as potential polytopic receptors

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Abstract

A series of disubstituted p-tert-butylcalix[4]arenes with N-methoxycarbonylmonoazacrown ether and N-ethoxymonoazacrown ether residues at the lower rim has been prepared via the reaction of di(carboxymethoxy)-p-tert-butylcalix[4]arene with azacrown ethers and subsequent reduction of the resulting amide derivatives. Using UV titration and 1H NMR spectroscopy we have demonstrated the ability of the calixarene with two N-carbonylmonoaza-18-crown-6-ether substituents to form the 1:3 complexes with K+ and Na+ and the 1:2 complexes with Cs+, Sr2+, Cu2+, and Zn2+. The calixarene with two fragments of N-ethoxymonoazo-18-crown ether has formed binuclear complexes with alkali metals cations and mononuclear complexes with transition metals cations.

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References

  1. Gutsche, C.D., Calixarenes, An Introduction, 2nd ed., Cambridge: RSC Publishing, 2008.

    Google Scholar 

  2. Creaven, B.S., Donlon, D.F., and McGinley, J., Coord. Chem. Rev., 2009, vol. 253, p. 893.

    Article  CAS  Google Scholar 

  3. Vicens, J. and Harrowfield, J., Calixarenes in the Tanoworld, Dordrecht: Springer, 2007, p. 394.

    Book  Google Scholar 

  4. Oueslati, I., Tetrahedron, 2007, vol. 63, no. 44, p. 10840.

    Article  CAS  Google Scholar 

  5. Tsukanov, A.V., Dubonosov, A.D., Bren’, V.A., and Minkin, V.I., Chem. Heterocycl. Comp., 2008, no. 8, pp. 899–923.

    Google Scholar 

  6. Ushakov, E.N., Alfimov, M.V., and Gromov, S.P., Russ. Chem. Rev., 2008, vol. 77, no. 1, p. 39.

    Article  CAS  Google Scholar 

  7. Iglesias-Sanchez, J.C., Wang, W., Ferdani, R., Prados, P., de Mendoza, J., and Gokel, G.W., New J. Chem., 2008, vol. 32, no. 5, p. 878.

    Article  Google Scholar 

  8. Yanaka, Y., Kobuke, Y., and Sokabe, M., Angew. Chem. Int. Ed., 1995, vol. 34, no. 6, p. 693.

    Article  Google Scholar 

  9. Cacciapaglia, R., Casnati, A., DiStefano, S., Mandolini, L., Pulemili, D., Reinhoudt, D.N., Sartori, A., and Ungaro, R., Chem. Eur. J., 2004, vol. 10, no. 18, p. 4436.

    Article  CAS  Google Scholar 

  10. Beer, P.D., Drew, M.G.B., Knubley, R.J., and Ogden, M.I., J. Chem. Soc. Dalton Trans., 1995, p. 3117.

    Google Scholar 

  11. Alekseeva, E.A., Luk’yanenko, A.P., Basok, S.S., Mazepa, A.V., and Gren’, A.I., Russ. J. Org. Chem., 2010, vol. 46, no. 9, p. 1403–1408.

    Article  CAS  Google Scholar 

  12. Vetrogon, V.I., Lukyanenko, N.G., Schwing-Weill, M.-J., and Arnaud-Neu, F., Talanta, 1994, vol. 41, p. 2105.

    Article  CAS  Google Scholar 

  13. Bentouhami, E., Bouet, G.M., Schwing, M.-J., and Khan, M.A., J. Solution Chem., 2006, vol. 35, p. 889.

    Article  CAS  Google Scholar 

  14. Kinard, W.F., Grant, P.M., and Baisden, P.A., Polyhedron, 1989, no. 8, p. 2385.

    Google Scholar 

  15. Roymon, J., Balaji, R., Amitabha, A., Anupam, K., and Chebrolu, P.R., J. Org. Chem., 2008, vol. 73, no. 15, p. 5745.

    Article  Google Scholar 

  16. Casnati, A., Barboso, S., Rouquette, H., SchwingWeill, M.-J., Arnaud-Neu, F., Dozol, J.-F., and Ungaro, R., J. Am. Chem. Soc., 2001, vol. 123, no. 49, p. 12182.

    Article  CAS  Google Scholar 

  17. Kim, H.J., Kim, S.K., Lee, J.Y., and Kim, J.S., J. Org. Chem., 2006, vol. 71, no. 17, p. 6611.

    Article  CAS  Google Scholar 

  18. Arnaud-Neu, F., Barrett, G., Fanni, S., Marrs, D., and McGregor, W., J. Chem. Soc., Perkin Trans. 2, 1995, no. 3, p. 453.

    Google Scholar 

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Correspondence to E. A. Alekseeva.

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Original Russian Text © E.A. Alekseeva, S.S. Basok, A.V. Mazepa, A.P. Luk’yanenko, O.V. Snurnikova, A.I. Gren’, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 9, pp. 1519–1525.

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Alekseeva, E.A., Basok, S.S., Mazepa, A.V. et al. p-tert-butylcalix[4]arenes containing azacrown ether substituents at the lower rim as potential polytopic receptors. Russ J Gen Chem 83, 1738–1743 (2013). https://doi.org/10.1134/S1070363213090181

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  • DOI: https://doi.org/10.1134/S1070363213090181

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