The Medium Effect on the Selective Complexation of Mercury (II) and Silver (I) by a Fully Substituted Lower Rim Calix[4]arene Receptor

  • Walther B. Aparicio Aragon Altiplano National University
  • Angela F. Danil de Namor University of Surrey
Keywords: Mercury, p-tert-Butylcalix[4]arene, Binding, potentiometry, conductometry, Protons, selectivity

Abstract

Mercury has been recognized as a highly dangerous element by the Environmental Protection Agency (EPA) due to its accumulative and persistent character in the environment and biota. In the Latin American region several countries are affected by the extremely high contents of mercury in the environmental and consequently in water, therefore the aim of this research is to synthesize receptors able to interact selectively with mercury species.

This paper reports the synthesis of a novel lower rim calix[4]arene derivative with pendent arms containing oxygen, phosphorus and sulphur as donor atoms, (1). Spectrometric (1H NMR) measurements were performed to determine the actives site of complexation of this ligand and the mercury (II) and silver (I) cations in solution. Conductance data provide information regarding the composition of the metal-ion complex in acetonitrile and methanol. The stability constant of the mercury (II) and silver (I) complex was derived from direct potentiometric titration. The latter technique was also used to characterize the thermochemical character of the binding process

Downloads

Download data is not yet available.

Author Biographies

Walther B. Aparicio Aragon, Altiplano National University

School of Chemical Engineering, Chemical Engineering Department, Altiplano National University, Puno/Peru

Angela F. Danil de Namor, University of Surrey

School of Biomedical and Molecular Sciences, Chemistry division, University of Surrey, Guildford, Surrey GU2 7XH

References

1. C.D. Gutsche and R. Muthukrishnan, “Analysis of the Product Mixtures Produced by the Base-Catalyzed Condensation of Formaldehyde with Para-Substituted Phenols”. J. Org. Chem., Vol: 43: Dec. 1978, pp. 4905-4906, DOI: 10.1021/jo00419a052
2. C.D. Gutsche, “Calixarenes. In: Monographs in Supramolecular Chemistry”, Ed. Stoddart, F.J. The Royal Society of Chemistry, London, 2008, ISBN: 978-1-84755-819-0, pp. 77-112.
3. J. Vicens and V. Böhmer “Calixarenes. In: A Versatile Class of Macrocyclic Compounds”, (Ed.). Kluwer Academic Publishers, Dordrecht, The Netherlands, 1991, ISBN: 0-7923-0714-3, pp. 200.
4. J. Vicens, Z. Asfari and J.M. Harrowfield “Calixarenes 50th Anniversary”: Commemorative Volume, Ed,; Kluwer Academic Publishers, Dordrecht, 1994, ISBN: 0-7923-3393-4, pp. 1-180.
5. C.D. Gutsche “Calixarenes “Revisited, in Monographs in Supramolecular Chemistry”; Ed. Stoddart, F.J.; The Royal Society of Chemistry; London , 1998, ISBN: 0-85404-502-3, pp. 79-114.
6. Z. Asfari, V. Böhmer, J. Harrowfield and J. Vicens “Calixarenes 2001”.; Ed. Kluwer Academic Publishers, 2001, ISBN: 0-7923-6960-2, pp. 1-89.
7. A.F. Danil de Namor; “Thermodynamics of host-guest interactions: Solubility enhancements”, Pure & Appl. Chem., Vol: 62, Jun 1990, pp. 2121-2127, doi:10.1351/pac199062112121
8. G.G. Talanova, H.-S. Hwang, V.S. Talanov and R.A. Bartsch; “Calix[4]arenes with a Novel Proton-Ionizable Group: Synthesis and Metal Ion Separations”, J. Chem. Soc. Chem. Commun. Mar. 1998, pp. 419-420. DOI: 10.1039/a708150b.
9. A. F. Danil de Namor, R.M. Cleverley and M.L. Zapata-Ormachea; “Thermodynamics of Calixarene Chemistry”, Chem. Rev. Vol: 98, Nov. 1998, pp. 2495-2526, PMID: 11848969.
10. F. Arnaud-Neu, S. Fanni, L. Guerra, W.M. McGregor, K.Ziat, M.J. Schwing-Weill, G. Barrett, M.A. McKervey, D. Marrs and E.M. Seward, “Cation complexation by chemically modified calixarenes. Part 7. Transport of alkali cations by p-tert-butylcalix[n]arene esters and amides”; J. Chem, Soc., Perkin Trans. 2, 1995, pp. 113-118. DOI: 10.1039/P29950000113
11. W. B. Aparicio-Aragon, PhD Thesis, 2005, University of Surrey.
12. S. Chahine, PhD Thesis, 2004, University of Surrey.
13. R. Perrin, L. Lamartine and M. Perrin; “The potential industrial applications of calixarenes”, Pure & Appl. Chem., Vol: 65, Nov. 1993, pp. 1549-1559, doi:10.1351/pac199365071549.
14. K. Araki, K. Akao, A. Ikeda, T. Susuki and S. Shinkai; “Molecular design of calixarene-based host molecules for inclusion of C60 in solution”, Tetrahedron Lett.,Vol: 37, Jan. 1996, pp. 73-76, doi:10.1016/0040-4039(95)02105-1
15. J.L. Atwood, G.A. Koutsantonis and C.L. Raston; “Purification of C60 and C70 by selective complexation with calixarenes”, Nature, Vol: 368, Mar. 1994, pp. 229-231, doi:10.1038/368229A0 (1994 K.P. Wainwright, PCT Int. Appl., WO 8908092, 1989).
16. R. M. Fuoss and K. L. Hsia, “Association of 1-1 Salts in Water”, Proc. Natl. Acad. Sci., Vol: 57, Jun. 1967, pp. 1550-1557, Bibliographic Code: 1967PNAS…57.1550F.
17. A. F. Danil de Namor, M.C. Cabaleiro, B.M. Vuano, M. Salomon, O.I. Pieroni, D.A. Pacheco Tanaka, C.Y. Ng, M.A. Llosa-Tanco, N.M. Rodriguez, J.D. Cardenas and A.R. Casal; “Thermodynamic and electrochemical aspects of the interactions of functionalised calix(4)arenes and metal cations in allosteric media”, Pure Appl. Chem., Vol: 66, 1994, pp. 435-440. doi:10.1351/pac199466030435
18. M. Izatt, J. J. Christensen and R. T. Hawkins, U.S. Patent 4, 477, 377, 16 Oct. 1984. (CA: 101:218333).
19. J. J. Christnesen, R. M. Izatt and Z. D. Hansen, “New Precision Thermometric Titrtation Calorimeter” The Rev. Sci. Instr., Vol: 36, Jun. 1965, pp 779-783, doi:10.1063/1.1719702
20. J. O. Hill, G. Öjelund and I. Wadsö; “Thermochemical results for Tris as a Test Substance in Solution Calorimetry”, J. Chem. Thermodyn., Vol. 1, Sept. 1969, pp. 111-116, doi:10.1016/0021-9614(69)90041-X
21. A.F. Danil de Namor, S. Chahine, D. Kowalska, E.E. Castellano and O.E. Piro; “Selective interaction of lower rim calix[4]arene derivatives and bivalent cations in solution. Crystallographic evidence of the versatile behavior of acetonitrile in lead(II) and cadmium(II) complexes”, J. Am. Chem. Soc. Vol. 124, Oct. 2002, pp. 12824-12836, DOI: 10.1021/ja020764+.
22. A. F. Danil de Namor, M.L.Zapata-Ormachea and R. Hutcherson; “The Medium Effect on the Thermodynamics of Complexation of 5,11,17,23-Tetrakis-(1,1-dimethylethyl)-25,27-bis(methylthio -ethoxy)- 26,28-bis[(diethylamine)ethoxy]calix(4) -arene and the Silver Cation”, J. Phys. Chem. B, Vol. 102, Sep. 1998, pp. 7839-7844, DOI: 10.1021/jp981778y
24. B.G. Cox, G.R. Hedwing, A.J. Parker and D.W. Watts; “Solvation of Ions. XIX Thermodynamic Properties for Transfer of Single Ions berween Protic and Dipolar Aprotic Solvents”, Aust. J. Chem. Vol. 27, 1974, pp. 477-501, doi:10.1071/CH9740477.
Published
2018-11-30
How to Cite
Aragon, W. B. A., & Namor, A. F. D. de. (2018). The Medium Effect on the Selective Complexation of Mercury (II) and Silver (I) by a Fully Substituted Lower Rim Calix[4]arene Receptor. IJRDO-Journal of Applied Science, 4(11), 20-26. https://doi.org/10.53555/as.v4i11.2498