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Synthesis of per-O-(carboxymethyl)calix[4]pyrogallols and their complexation with some alkaline metal and lanthanide ions

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Abstract

Complexones of a new class, viz., carboxy-functionalized calix[4]pyrrogallols, were synthesized. The per-O-(carboxymethyl)calix[4]pyrogallols obtained were established to exist in the (rel, cis, trans, trans)-configuration by 2D NMR spectroscopic data. According to the pH-potentiometric data, the interaction of these compounds with alkaline metal ions (Li+, Na+, K+, Cs+) and lanthanide ions (La3+, Gd3+, Lu3+) in a water—DMSO system produces 1 : 1 complexes. The specific features of complexation of per-O-(carboxymethyl)calix[4]pyrogallols, as compared to their acyclic analogs, with alkaline metal and lanthanide ions are due to the cooperative effect of donor groups preorganized on the calixarene matrix.

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References

  1. G. R. Choppin, A. Dadgar, and E. N. Rizkalla, Inorg. Chem., 1986, 25, 3581.

    Google Scholar 

  2. K. Ohto, M. Yano, K. Inoue, T. Yamamoto, M. Goto, F. Nakashio, S. Shinkai, and T. Nagasaki, Anal. Sciences, 1995, 11, 893.

    Google Scholar 

  3. K. Ohto, M. Yano, K. Inoue, T. Yamamoto, T. Nagasaki, M. Goto, F. Nakashio, and S. Shinkai, Polyhedron, 1997, 16, 1655.

    Google Scholar 

  4. M. H. B. Grote Gansey, W. Verboom, F. C. J. M. van Veggel, V. Vetrogon, F. Arnaud-Neu, M.-J. Schwing-Weill, and D. N. Reinhoudt, Chem. Soc., Perkin Trans. 2, 1998, 2351.

  5. W. Sliwa, T. Zujewska, and B. Bachowska, Pol. J. Chem., 2003, 77, 1079.

    Google Scholar 

  6. C. D. Gutsche, in Calixarenes 2001, Eds. Z. Asfari, V. Bohmer, and J. Vicens Harrowfield, Kluwer Academic Publishers, Dordrecht-Boston-London, 2001, 10.

    Google Scholar 

  7. H.-J. Shchneider, D. Guttes, and U. Schneider, J. Am. Chem. Soc., 1988, 110, 6449.

    Google Scholar 

  8. C. N. Pod'yachev, A. R. Mustafina, and W. D. Habicher, Izv. Akad. Nauk, Ser. Khim., 2003, 70 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1].

  9. A. W. Archer and P. A. Claret, J. Chem. Soc., Sect. C., 1970, 1296.

  10. A. Giacosa, J. Praktisch. Chemie, 1879, 2, 396.

    Google Scholar 

  11. Technique of Organic Chemistry. V. VII. Organic Solvents. Physical Properties and Methods of Purification, Ed. A. Weissberger, Interscience Publisher, New York, 1955, 472 pp.

    Google Scholar 

  12. V. V. Aleksandrov, Kislotnost´ nevodnykh rastvorov [Acidity of Nonaqueous Solutions], Vishcha Shkola, Khar´kov, 1982, 159 pp. (in Russian).

    Google Scholar 

  13. O. Popovych, Anal. Chem., 1964, 36, 878.

    Google Scholar 

  14. Yu. I. Sal´nikov, A. N. Glebov, and F. V. Devyatov, Poliyadernye kompleksy v rastvorakh [Polynuclear Complexes in Solutions], Izd-vo KGU, Kazan, 1989, 287 pp. (in Russian).

    Google Scholar 

  15. L. Eberson, in The Chemistry of Carboxylic Acids and Esters, Ed. S. Patai, Interscience, New York, 1969, p. 272.

    Google Scholar 

  16. G. Arena, R.P. Bonomo, R. Cali, F. G. Gulino, G. G. Lombardo, D. Sciotto, R. Ungaro, and A. Casnati, Supra-molecular Chemistry, 1995, 4, 287.

    Google Scholar 

  17. T. Nagasaki, T. Arimura, and S. Shinkai, Bull. Chem. Soc. Jpn, 1991, 64, 2575.

    Google Scholar 

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Pod"yachev, S.N., Mustafina, A.R., Koppehele, A.H. et al. Synthesis of per-O-(carboxymethyl)calix[4]pyrogallols and their complexation with some alkaline metal and lanthanide ions. Russian Chemical Bulletin 53, 1181–1188 (2004). https://doi.org/10.1023/B:RUCB.0000042271.85945.3d

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  • DOI: https://doi.org/10.1023/B:RUCB.0000042271.85945.3d

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