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Synthesis, complexation and use of calix[4]crown-6 as a novel neutral ionophore for the preparation of a selective and sensitive PVC-membrane potentiometric sensor for Ba2+ ion

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Abstract

Calix[4]crown-6 (L) was synthesized and the stoichiometry and stability of its complexes with alkali, alkaline earth, Ag+, Tl+ and NH4 + ions were studied conductometrically in acetonitrile solution. The resulting 1:1 Ba2+-L complex was found to be the most stable one among all cation complexes studied. The optimized structures of the ligand and its Ba2+ complex are also reported. Based on the findings, L was used as a suitable ionophore to prepare a PVC-membrane selective electrode for Ba2+ ion. The electrode revealed a Nernstian behavior over wide barium ion concentration 1.0 × 10−6 to 1.0 × 10−3 M with only little trace of 7.1 × 10−7 M. The potentiometric responses were found to be independent of the pH of test solutions in the range of 4.0–10.0. The proposed electrode response time of about 10 s proved to be highly selective for Ba2+ ion over a wide variety of cations including alkali, alkaline earth, transition and heavy metal ions. The sensor could be used for at least three months without any noticeable deviation. The practical utility of the proposed electrode was also examined.

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References

  1. http://www.lenntech.com/periodic/elements/ba.htm

  2. A.K. Singh, R. Singh, R.P. Singh, P. Saxena, Sens. Actuators B 106 (2005) 779.

    Google Scholar 

  3. http://www.globalhealingcenter.com/dangers-ofbarium.html

  4. S.S.M. Hassan, M.B. Saleh, A.A. Abdel Gaber, N.A. Abdel Kream, Talanta 59 (2003) 161.

    CAS  Google Scholar 

  5. H.A. Zamani, J. Abedini-Torghabeh, M.R. Ganjali, Electroanalysis 18 (2006) 888.

    Google Scholar 

  6. A.M. Othman, M.S. El-Shahawi, M. Abdel-Azeem, Anal. Chim. Acta 555 (2006) 322.

    CAS  Google Scholar 

  7. H.A. Zamani, M.T. Hamed-Mosavian, E. Aminzadeh, M.R. Ganjali, M. Ghaemy, H. Behmadi, F. Faridbod, Desalination 250 (2010) 56.

    CAS  Google Scholar 

  8. C.D. Gutsche, Calixarenes. The Royal Society of Chemistry, Cambridge, UK, 1989.

    Google Scholar 

  9. J. Vincens, V. Bohmer, Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer: Dordrecht, The Netherlands, 1991.

  10. A. Ikeda, S. Shinkai, Chem. Rev. 97 (1997) 1713.

    CAS  Google Scholar 

  11. A.F.D. de Namor, R.M. Cleverley, M.L. Zapata- Ormachea, Chem. Rev. 98 (1998) 2495.

    Google Scholar 

  12. N. Morohashi, F. Narumi, N. Iki, T. Hattori, S. Miyano, Thiacalixarenes. Chem. Rev. 106 (2006) 5291.

    CAS  Google Scholar 

  13. B.S. Creaven, D.F. Donlon, J. McGinley, Coord. Chem. Rev. 253 (2009) 893.

    CAS  Google Scholar 

  14. P. Thuery, M. Nierlich, C. Bressot, V. Lamare, J.F. Dozol, Z. Asfari, J. Vicens, J. Incl. Phenom. 23 (1996) 305.

    Google Scholar 

  15. P. Thuery, M. Nierlich, Z. Asfari, J. Vicens, J. Incl. Phenom. 27 (1997) 169.

    CAS  Google Scholar 

  16. Z. Asfari, X. Nicoille, J. Vicens, J. Incl. Phenom. 33 (999) 2511.

  17. A. Mathieu, Z. Asfari, J. Vicens, Tetrahedron Lett. 43 (2002) 1225.

    CAS  Google Scholar 

  18. H.M. Chawla, S.P. Singh, S. Upreti, Tetrahedron 63 (2007) 5636.

    CAS  Google Scholar 

  19. C. Tu, K. Surowiec, J. Gega, D.W. Purkiss, R.A. Bartsch, Tetrahedron 64 (2008) 1187.

    CAS  Google Scholar 

  20. A. Mathieu, Z. Asfari, J. Vicens, Tetrahedron Lett. 43 (2002) 1225.

    CAS  Google Scholar 

  21. H.M. Chawla, S.P. Singh, S. Upreti, Tetrahedron 63 (2007) 5636.

    CAS  Google Scholar 

  22. C. Tu, K. Surowiec, J. Gega, D.W. Purkiss, R.A. Bartsch, Tetrahedron 64 (2008) 1187.

    CAS  Google Scholar 

  23. M. Surowiec, R. Custelcean, K. Surowiec, R.A. Bartsch, Tetrahedron 65 (2009) 7777.

    CAS  Google Scholar 

  24. H. Haddadi, N. Alizadeh, M. Shamsipur, Z. Asfari, J. Phys. Chem. A 114 (2010) 7462.

    CAS  Google Scholar 

  25. H. Haddadi, N. Alizadeh, M. Shamsipur, Z. Asfari, V. Lippolis, C. Bazzicalupi, Inorg. Chem. 49 (2010) 6874.

    CAS  Google Scholar 

  26. P. Buhlmann, E. Pretsch, E. Bakker, Chem. Rev. 98 (1998) 1593.

    Google Scholar 

  27. E. Bakker, P. Buhlmann, E. Pretsch, Electroanalysis 11 (1999) 915.

    CAS  Google Scholar 

  28. R. Ludwig, N.T. Dzung, Sensors 2 (2000) 397.

    Google Scholar 

  29. R.K. Mahajan, M. Kumar, V. Sharma, I. Kaur, Talanta 58 (2002) 445.

    CAS  Google Scholar 

  30. M. Arvand-Barmchi, M.F. Mousavi, M.A. Zanjanchi, M. Shamsipur, S. Taghavi, Anal. Lett. 35 (2002) 767.

    CAS  Google Scholar 

  31. A. Casnati, N. Della Ca’, F. Sansone, F. Ugozzoli, R. Ungaro, Tetrahedron 60 (2004) 7869.

    CAS  Google Scholar 

  32. J.H. Bok, H.J. Kim, J.W. Lee, S.K. Kim, J.K. Choi, J. Vicens, J.S. Kim, Tetrahedron Lett. 47 (2006) 1237.

    CAS  Google Scholar 

  33. M.F. Mahon, J. McGinley, A. Denise Rooney, J.M.D. Walsh, Tetrahedron 64 (2008) 11058.

    CAS  Google Scholar 

  34. Y. Yang, X. Cao, M. Surowiec, R.A. Bartsch, Tetrahedron 66 (2010) 447.

    CAS  Google Scholar 

  35. P.S. Ramanjaneyulu, P. Singh, Y.S. Sayi, H.M. Chawla, K.L. Ramakumar, J. Hazard. Mat. 175 (2010) 12031.

    Google Scholar 

  36. A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud, S. Fanni, M.-J. Schwing, R.J.M. Egberink, F. de Jong, D.N. Reinhoudt, J. Am. Chem. Soc. 117 (1995) 2767.

    CAS  Google Scholar 

  37. J.S. Kim, W.K. Lee, W. Sim, J.W. Ko, M.H. Cho, D.Y. Ra, J.W. Kim, J. Incl. Phenom. 37 (2000) 359.

    CAS  Google Scholar 

  38. S. Kamata, A. Bhale, Y. Fukunaga, H. Murata, Anal. Chem. 60 (1988) 2464.

    CAS  Google Scholar 

  39. Y. Takeda, Bull. Chem. Soc. Jpn. 56 (1983) 3600.

    CAS  Google Scholar 

  40. D.P. Zollinger, F. Bulten, A. Christenhuse, M. Bos, W.E. Van Der Linden, Anal. Chim. Acta 198 (1987) 207.

    CAS  Google Scholar 

  41. V.A. Nicely, J.L. Dye, J. Chem. Educ. 48 (1971) 443.

    Google Scholar 

  42. M. Shamsipur, M. Saeidi, J. Solution Chem. 29 (2000) 1187.

    CAS  Google Scholar 

  43. R.D. Shannon, Acta Chrystallogr. A 32 (1976) 751.

    Google Scholar 

  44. Hyperchem, Release 7.0, Hypercube, Inc., Gainesville, 2002.

  45. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98 (Revision A.7). Gaussian Inc., Pittsburgh PA, 1998

    Google Scholar 

  46. M.Z. Kassaee, M. Beigi, S. Arshadi, J. Mol. Struct. (Theochem.) 624 (2003) 69.

    CAS  Google Scholar 

  47. S.K. Sahoo, M. Baral, B.K. Kanungo, Polyhedron 25 (2006) 722.

    CAS  Google Scholar 

  48. E. Bakker, P. Buhlmann, E. Pretsch, Chem. Rev. 97 (1997) 3083.

    CAS  Google Scholar 

  49. M. Shamsipur, S. Sadeghi, H. Naeimi, H. Sharghi, Polish J. Chem. 74 (2000) 231.

    CAS  Google Scholar 

  50. M. Shamsipur, M.H. Mashhadizadeh, Talanta 53 (2001) 1065.

    CAS  Google Scholar 

  51. M.R. Ganjali, T. Poursaberi, F. Basiripour, M. Salavati- Niassari, M. Yousefi, M. Shamsipur, Fresenius J. Anal. Chem. 370 (2001) 1091.

    CAS  Google Scholar 

  52. M.R. Ganjali, M. Tahami, M. Shamsipur, T. Poursaberi, S. Haghgoo, M. Hosseini, Electroanalysis 15 (2003) 1038.

    CAS  Google Scholar 

  53. T. Rosatzin, E. Bakker, K. Suzuki, W. Simon, Anal. Chim. Acta 280 (1993) 197.

    CAS  Google Scholar 

  54. U. Schaller, E. Bakker, U.E. Spichiger, E. Pretsch, Anal. Chem. 66 (1994) 391.

    CAS  Google Scholar 

  55. P.M. Gehrig, W.E. Mori, M. Welti, E. Pretsch, Helv. Chim. Acta 73 (1990) 203.

    CAS  Google Scholar 

  56. IUPAC Analytical Chemistry Division, Commission on Analytical Nomenclature, Recommendation for Nomenclature of Ion Selective Electrode, Pure Appl. Chem. 48 (1976) 127.

    Google Scholar 

  57. Y. Umezawa, K. Umezawa, H. Sato, Pure Appl. Chem. 67 (1995) 507.

    Google Scholar 

  58. G.A. Rechnitz, M.R. Kresz, S.B. Zamochnick, Anal. Chem. 38 (1966) 973.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Razi University, Kermanshah, Iran

    S. Sahari & M. Shamsipur

  2. Department of Chemistry, Payame Noor University (PNU), Ardakan, Iran

    M. Taghdiri

  3. Department of Chemistry, Lorestan University, Khorramabad, Iran

    Z. Asfari

  4. Laboratoire de Chimie Analytique et Minerale, UMR 778, ULP/CNRS/ IN2P3(LC4), ECPM, 25 Rue Becquerel, F-67087, Strasbourg Cedex, France

    K. Alizadeh

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  1. S. Sahari
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  2. M. Taghdiri
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  3. K. Alizadeh
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  4. Z. Asfari
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  5. M. Shamsipur
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Correspondence to M. Shamsipur.

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Sahari, S., Taghdiri, M., Alizadeh, K. et al. Synthesis, complexation and use of calix[4]crown-6 as a novel neutral ionophore for the preparation of a selective and sensitive PVC-membrane potentiometric sensor for Ba2+ ion. JICS 8, 879–888 (2011). https://doi.org/10.1007/BF03245919

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