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The extraction of thallium(I) and silver(I) ions with 1,3-alternate calix[4]arene derivatives

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Abstract

Tetraallyloxy and tetrabenzyloxy derivatives of calix[4]arenes in cone and 1,3-alternate conformations were synthesised and their capacity to extract thallium(I) and silver(I) ions was investigated. ‘Low’-temperature single crystal X-ray structure determinations were recorded for two derivatives in which the calixarene conformation was that of an alternating cone, the aromatic rings lying closely quasi-parallel to the \( \overline{4} \)-axis of the cone. The structure of a tetraallyloxy derivative in the cone conformation was also determined in which a molecule of acetonitrile was included within the calixarene cavity.

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Notes

  1. Calixarene nomenclature follows that recommended by IUPAC. See: Favre et al. [36].

References

  1. Gutsche, C.D.: Calixarenes: An Introduction, 2nd edn. RSC, Cambridge (2008)

    Google Scholar 

  2. Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.): Calixarenes 2001. Kluwer Academic Press, Dordrecht (2001)

    Google Scholar 

  3. Mandolini, L., Ungaro, R. (eds.): Calixarenes in Action. Imperial College Press, London (2000)

    Google Scholar 

  4. Vicens, J., Harrowfield, J. (eds.): Calixarenes in the Nanoworld. Springer, Dordrecht (2006)

    Google Scholar 

  5. Homden, D.M., Redshaw, C.: The use of calixarenes in metal-based catalysis. Chem. Rev. 108(12), 5086–5130 (2008). doi:10.1021/cr8002196

    Article  CAS  Google Scholar 

  6. Sliwka-Kaszynska, M.: Calixarenes as stationary phases in high performance liquid chromatography. Crit. Rev. Anal. Chem. 37(3), 211–224 (2007). doi:10.1080/10408340701244672

    Article  CAS  Google Scholar 

  7. Creaven, B.S., Donlon, D.F., McGinley, J.: Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications. Coord. Chem. Rev. 253(7–8), 893–962 (2009). doi:10.1016/j.ccr.2008.06.008

    Article  CAS  Google Scholar 

  8. Shokova, E., Kovalev, V.: Calixarene-based anionic receptors. Russ. J. Org. Chem. 45(9), 1275–1314 (2009)

    Article  CAS  Google Scholar 

  9. El Nashar, R.M., Wagdy, H.A.A., Aboul-Enein, H.Y.: Applications of calixarenes as potential ionophores for electrochemical sensors. Curr. Anal. Chem. 5(3), 249–270 (2009)

    Article  CAS  Google Scholar 

  10. Kimura, K., Tatsumi, K., Yokoyama, M., Ouchi, M., Mocerino, M.: Remarkable thallium(I) selectivity for ion sensors based on π-coordination of calix[4]arene neutral carriers. Anal. Commun. 36(6), 229–230 (1999)

    Article  CAS  Google Scholar 

  11. Yoshioka, N., Yajima, S., Kimura, K.: Silver ion sensing using π-coordinate aromatic neutral carriers for soft metal ions. Bunseki Kagaku 52(9), 689–694 (2003)

    Article  CAS  Google Scholar 

  12. Harrowfield, J.M., Mocerino, M., Peachey, B.J., Skelton, B.W., White, A.H.: Rare-earth-metal solvent extraction with calixarene phosphates. J. Chem. Soc.-Dalton Transact. (8), 1687–1699 (1996)

  13. Ohto, K.: Review of the extraction behavior of metal cations with calixarene derivatives. Solvent Extr. Res. Dev. Jpn. 17, 1–18 (2010)

    CAS  Google Scholar 

  14. Mokhtari, B., Pourabdollah, K., Dallali, N.: A review of calixarene applications in nuclear industries. J. Radioanal. Nucl. Chem. 287(3), 921–934 (2011). doi:10.1007/s10967-010-0881-1

    Article  CAS  Google Scholar 

  15. Li, Z.Y., Chen, J.W., Liu, Y., Xia, W., Wang, L.Y.: The use of calixarenes in asymmetric catalysis. Curr. Org. Chem. 15(1), 39–61 (2011)

    Article  CAS  Google Scholar 

  16. Ouchi, M., Hakushi, T.: Cation binding by thallium(I) selective crown ethers. Coord. Chem. Rev. 148, 171–181 (1996)

    Article  CAS  Google Scholar 

  17. Kudo, Y., Usami, J., Katsuta, S., Takeda, Y.: Solvent extraction of silver picrate by 3 m-crown-m ethers (m = 5, 6) and its mono-benzo-derivative from water into benzene or chloroform: elucidation of an extraction equilibrium using component equilibrium constants. Talanta 62(4), 701–706 (2004). doi:10.1016/j.talanta.2003.09.022

    Article  CAS  Google Scholar 

  18. Couton, D., Mocerino, M., Rapley, C., Kitamura, C., Yoneda, A., Ouchi, M.: Silver and thallium ion complexation with allyloxycalix[4]arenes. Aust. J. Chem. 52(3), 227–229 (1999)

    Article  CAS  Google Scholar 

  19. Cuc, D., Bouguet-Bonnet, S., Morel-Desrosiers, N., Morel, J.-P., Mutzenhardt, P., Canet, D.: Behavior of cesium and thallium cations inside a calixarene cavity as probed by nuclear spin relaxation evidence of cation-π interactions in water. J. Phys. Chem. B 113(31), 10800–10807 (2009)

    Article  CAS  Google Scholar 

  20. Ikeda, A., Shinkai, S.: Unusually high ionophoricity of 1,3-alternate-calix[4]arenes: π-Donor participation in the complexation of cations? Tetrahedron Lett. 33(48), 7385–7388 (1992). doi:10.1016/s0040-4039(00)60194-6

    Article  CAS  Google Scholar 

  21. Matthews, S.E., Rees, N.H., Felix, F., Drew, M.G.B., Beer, P.D.: Thallium π-cation complexation by calix[4] tubes: Tl-205 NMR and X-ray evidence. Inorg. Chem. 42(3), 729–734 (2003). doi:10.1021/ic025884x

    Article  CAS  Google Scholar 

  22. Matthews, S.E., Schmitt, P., Felix, V., Drew, M.G.B., Beer, P.D.: Calix[4]tubes: a new class of potassium-selective ionophore. J. Am. Chem. Soc. 124(7), 1341–1353 (2002). doi:10.1021/ja011856m

    Article  CAS  Google Scholar 

  23. Ghidini, E., Ugozzoli, F., Ungaro, R., Karkema, S., El-Gadl, A.A., Reinhoudt, D.N.: Complexation of alkali metal cations by conformationally rigid, stereoisomeric crown ethers: a quantitative evaluation of preorganization. J. Am. Chem. Soc. 112, 6979–6985 (1990)

    Article  CAS  Google Scholar 

  24. Park, C., Chun, S.K., Bartsch, R.A.: Effect of conformation on metal ion extraction by calix[4]arene dicarboxylic acids. J. Incl. Phenom. Macrocycl. Chem. 66(1–2), 95–105 (2010). doi:10.1007/s10847-009-9650-6

    Article  CAS  Google Scholar 

  25. Shinkai, S., Fujimoto, K., Otsuka, T., Ammon, H.L.: Synthesis and ion selectivity of conformational isomers derived from calix[4]arenes. J. Org. Chem. 57, 1516–1523 (1992)

    Article  CAS  Google Scholar 

  26. Tabakci, M.: Synthesis and evaluation of extraction ability of calix[4]-crown-6 cone conformer and its oligomeric analogue. React. Funct. Polym. 58(1), 27–34 (2004). doi:10.1016/j.reactfunctpolym.2003.11.002

    Article  CAS  Google Scholar 

  27. Gutsche, C.D., Dhawan, B., Levine, J.A., Hyun No, K., Bauer, L.J.: Calixarenes 9 conformational isomers of the ethers and esters of calix[4]arenes. Tetrahedron 39(3), 409–426 (1983). doi:10.1016/s0040-4020(01)88541-0

    Article  CAS  Google Scholar 

  28. Gutsche, C.D., Reddy, P.A.: Calixarenes 25. Conformations and structures of the products of arylmethylation of calix[4]arenes. J. Org. Chem. 56(15), 4783–4791 (1991)

    Article  CAS  Google Scholar 

  29. Dijkstra, P.J., Brunink, J.A.J., Bugge, K.E., Reinhoudt, D.N., Harkema, S., Ungaro, R., Ugozzoli, F., Ghidini, E.: Kinetically stable complexes of alkali cations with rigidified calix[4]arenes—synthesis, X-ray structures, and complexation of calixcrowns and calixspherands. J. Am. Chem. Soc. 111(19), 7567–7575 (1989)

    Article  CAS  Google Scholar 

  30. Arduini, A., Casnati, A.: Calixarenes. In: Parker, D. (ed.) Macrocycle Synthesis: A Practical Approach, pp. 145–173. Oxford University Press, Oxford (1996)

  31. Sharma, S.K., Alam, I., Gutsche, C.D.: Selective arylmethylation, arylmethenylation and aroylation of mono-p-cyano-methylcalix[4]arene and tetra-p-cyano-methylcalix[4]arene. Synthesis (9), 1089 (1995)

  32. Sheldrick, G.M.: A short history of SHELX. Acta Crystallogr. A 64, 112–122 (2008)

    Article  Google Scholar 

  33. Maeda, T., Kimura, K., Shono, T.: Solvent-extraction of silver and thallium picrates with poly-(crown ether)s and bis-(crown ether)s. Fresen. Z. Anal. Chem. 298(5), 363–366 (1979)

    Article  CAS  Google Scholar 

  34. Wong, K.H., Ng, H.L.: Complexes of sodium, potassium, rubidium and cesium picrates with bis-crown ethers. J. Coord. Chem. 11(1), 49–55 (1981)

    Article  CAS  Google Scholar 

  35. Asfari, Z., Bilyk, A., Bond, C., Harrowfield, J.M., Koutsantonis, G.A., Lengkeek, N., Mocerino, M., Skelton, B.W., Sobolev, A.N., Strano, S., Vicens, J., White, A.H.: Factors influencing solvent adduct formation by calixarenes in the solid state. Org.Biomol. Chem. 2(3), 387–396 (2004). doi:10.1039/b308214h

    Article  CAS  Google Scholar 

  36. Favre, H.A., Hellwinkel, D., Powell, W.H., Smith, H.A. Jr., Tsay, S.S.-C. Pure Appl. Chem. 74, 809.(2002)

    Google Scholar 

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Authors and Affiliations

  1. Nanochemistry Research Institute, Department of Chemistry, Curtin University, GPO Box U 1987, Perth, WA, 6845, Australia

    Ryan T. Chester, Daniel Couton, Roya Lobler, Mauro Mocerino, Mark I. Ogden & Jade K. Pettersen

  2. Chemistry M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, Crawley, WA, 6009, Australia

    Brian W. Skelton & Allan H. White

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  1. Ryan T. Chester
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  2. Daniel Couton
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Correspondence to Mauro Mocerino.

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Dedicated to Len Lindoy on the occasion of his 75th birthday and in recognition of his great contribution to the field of macrocyclic chemistry.

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Chester, R.T., Couton, D., Lobler, R. et al. The extraction of thallium(I) and silver(I) ions with 1,3-alternate calix[4]arene derivatives. J Incl Phenom Macrocycl Chem 71, 471–477 (2011). https://doi.org/10.1007/s10847-011-0010-y

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