Skip to main content
Log in

Spectrophotometric Determination of Equilibrium Constants of Dimethyl and Diethyltin(IV) Dichloride with 5,10,15,20-Tetrakis(4-trimethyl-ammonio-phenyl)-prophine Tetratosylate

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

The formation constant of dimethyl and diethyltin(IV) dichloride hydrolytic species and their complexation reactions with 5,10,15,20-tetrakis(4-trimethyl-ammonio-phenyl)-prophine tetratosylate (TTMAPP) were evaluated using potentiometric and spectrophotometric methods. 1H NMR spectra of dimethyl and diethyltin(IV) at different pHs have an octahedral structure in low pHs and a distorted trigonal bipyramidal structural arrangement at higher pH values. The compositions of the formed complexes were determined, and it was shown that they form a single mononuclear 1:1 species with the ligand. The results indicate that the formation constants are in the order Me2Sn(IV)–TTMAPP > Et2Sn(IV)–TTMAPP.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Longo, F.R., Brown, E.M., Rew, W., Adler, A.D.: The Porphyrins. Academic Press, New York (1980)

    Google Scholar 

  2. Kadish, K., Amith, K.M., Guillard, R.: The Porphyrin Handbook. Academic Press, New York (1999)

    Google Scholar 

  3. Vergeldt, F.J., Koehorst, R.B.M., Schaafsma, T.J., Lambry, J.C., Martin, J.L., Johnson, D.G., Wasielewski, M.R.: Sub-picosecond photoinduced electron transfer in water-soluble porphyrin dimers. Chem. Phys. Lett. 182, 107–113 (1991)

    Article  CAS  Google Scholar 

  4. Darwent, J.R., Douglas, P., Harriman, A., Porter, G., Richoux, M.C.: Metal phthalocyanines and porphyrins as photosensitizers for reduction of water to hydrogen. Coord. Chem. Rev. 44, 83–126 (1982)

    Article  CAS  Google Scholar 

  5. Maree, C.H.M., Roosendaal, S.J., Savenije, T.J., Schropp, R.E.I., Schaafsma, T.J., Habraken, F.H.P.M.: Photovoltaic effects in porphyrin polymer films and heterojunctions. J. Appl. Phys. 80, 3381–3389 (1996)

    Article  CAS  Google Scholar 

  6. Vasil’ev, V.V., Blinova, I.A., Golovina, I.V., Borisov, S.M.: Photophysical and photochemical properties of the water-soluble porphyrin complexes of metals of the platinum group. J. Appl. Spect. 66, 583–587 (1999)

    Article  Google Scholar 

  7. Bonnett, R.: Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chem. Soc. Rev. 24, 19–33 (1995)

    Article  CAS  Google Scholar 

  8. Davies, A.G., Smith, P.J.: Tin. In: Wilkinson, G., Stone, F.G.A., Abel, E.W. (eds.) Comprehensive Organometallic Chemistry, pp. 519–627. Pergamon Press, Oxford (1982)

    Chapter  Google Scholar 

  9. Molloy, K.C.: The Chemistry of Tin. Blackie, Glasgow (1989)

    Google Scholar 

  10. Gharib, F., Mohammadpour Amini, M., Haghgou, A.: Hydrolysis of dimethyltin(IV) dichloride in different ionic media. Main Group Met. Chem. 26, 381–390 (2003)

    Article  CAS  Google Scholar 

  11. Gharib, F., Farzad, E., Mohammadpour Amini, M.: Interaction of dimethyltin(IV) dichloride with 5′-AMP and 5′-GMP. Can. J. Chem. 84, 1534–1540 (2006)

    Article  CAS  Google Scholar 

  12. Gharib, F., Jaberi, F., Zandevakili, M.: Interaction of dimethyltin(IV) dichloride with 5′-IMP and 5′-UMP. Appl. Organometal. Chem. 22, 215–220 (2008)

    Article  CAS  Google Scholar 

  13. Jabbari, M., Gharib, F., Mohammadpour Amini, M., Azadmehr, A.: Hydrolysis of dimethylphenyltin(IV) and triphenyltin(IV) chlorides in different aqueous ethanol solutions. Can. J. Chem. 86, 751–756 (2008)

    Article  Google Scholar 

  14. Mehdizadeh, S., Jabbari, M., Shakibazadeh, R., Gharib, F.: Hydrolysis of diphenylmethyltin(IV) chloride in different aqueous solutions of ethanol. Heteroatom Chem. 19, 654–660 (2008)

    Article  CAS  Google Scholar 

  15. Jabbari, M., Gharib, F.: Equilibrium studies of triphenyltin(IV) complexes with glycine, glycyl-glycine, and glycyl-glycyl-glycine in different aqueous solutions of ethanol. Can. J. Chem. 88, 877–885 (2010)

    Article  CAS  Google Scholar 

  16. Surdy, P., Rubini, P., Buzas, N., Henry, B., Pellerito, L., Gajda, T.: Interaction of dimethyltin(IV)2+ cation with Gly-Gly, Gly-His, and some related ligands. A new case of a metal ion able to promote peptide nitrogen deprotonation in aqueous solution. Inorg. Chem. 38, 346–352 (1999)

    Article  CAS  Google Scholar 

  17. Gajda-Schrantz, K., Jancso, A., Pettinari, C., Gajda, T.: Thiolate anchor in organotin(IV) induced amide deprotonation: equilibrium and NMR spectroscopic studies on dimethyltin(IV) complexes formed with N-(2-mercaptopropionyl)glycine and L-alanyl-glycine. J. Chem. Soc. Dalton Trans. 2912–2916 (2003). doi:10.1039/B303905F

  18. Hynes, M.J., O’Dowd, M.: Interactions of the trimethyltin(IV) cation with carboxylic acids, amino acids, and related ligands. J. Chem. Soc. Dalton Trans. 563–566 (1987). doi:10.1039/DT9870000563

  19. Gajda-Schrantz, K., Nagy, L., Fiore, T., Pellerito, L., Gajda, T.: Equilibrium and spectroscopic studies of dimethyltin(IV) complexes formed with hydroxymono- and di-carboxylic acids and their thioanalogues. J. Chem. Soc. Dalton Trans. 152–158 (2002). doi:10.1039/B105263M

  20. Shoukry, M.M.: Equilibrium studies of the diorganotin(IV) complexes with some amino acids and related compounds. Talanta 43, 177–183 (1996)

    Article  CAS  Google Scholar 

  21. Jancso, A., Gajda, T., Szorcsik, A., Kiss, T., Henry, B., Vanko, G., Rubini, P.: Potentiometric and spectroscopic studies on dimethyltin(IV) complexes of 2-hydroxyhippuric acid. J. Inorg. Biochem. 83, 187–192 (2001)

    Article  CAS  Google Scholar 

  22. Shoukry, M.M., Mohamed, M.M.H.: Complex equilibria involving triphenyltin(IV) with some selected amino acids and nucleotides. J. Coord. Chem. 43, 217–225 (1998)

    Article  CAS  Google Scholar 

  23. Jancso, A., Henry, B., Rubini, P., Vanko, G., Gajda, T.: Dimethyltin(IV) cation induced amide deprotonation of aspartic acid containing dipeptides. J. Chem. Soc. Dalton Trans. 1941–1947 (2000). doi:10.1039/A909741D

  24. Cardiano, P., Giuffre, O., Pellerito, L., Pettignano, A., Sammartano, S., Scopelliti, M.: Thermodynamic and spectroscopic study of the binding of dimethyltin(IV) by citrate at 25°C. Appl. Organomet. Chem. 20, 425–435 (2006)

    Article  CAS  Google Scholar 

  25. Gharib, F., Jaberi, F., Shamel, A., Farzaneh, P., Babashpour, S., Moazzami, M.: Equilibrium studies of the dimethyltin(IV) complexes with tyrosine, tryptophan, and phenylalanine. J. Chem. Eng. Data 56, 3128–3132 (2011)

    Article  CAS  Google Scholar 

  26. Yang, P., Guo, M.: Interactions of organometallic anticancer agents with nucleotides and DNA. Coord. Chem. Rev. 185, 189–211 (1999)

    Article  Google Scholar 

  27. Buzas, N., Gajda, G.T., Nagy, L., Kuzmann, E., Vertes, A.: Unusual coordination behavior of d-fructose towards dimethyltin(V): metal-promoted deprotonation of alcoholic OH groups in aqueous solutions of low pH. Inorg. Chim. Acta 274, 167–176 (1998)

    Article  CAS  Google Scholar 

  28. Szorcsik, A., Nagy, L., Sletten, J., Szalontai, G., Kamu, E., Fiore, T., Pellerito, L., Kalman, E.: Preparation and structural studies on dibutyltin(IV) complexes with pyridine mono- and dicarboxylic acids. J. Organomet. Chem. 689, 1145–1154 (2004)

    Article  CAS  Google Scholar 

  29. Al-Flaijj, O., Shehata, M.R., Mohamed, M.M., Shoukry, M.M.: Interaction of dimethyltin(IV) with DNA constituents. Monatsh. Chem. 132, 349–366 (2001)

    Article  CAS  Google Scholar 

  30. Arena, G., Purrello, R., Rizzarelli, E., Gianguzza, A., Pellerito, L. Thermodynamics of hydroxo complex formation of dialkyltin(IV) ions in aqueous solution. J. Chem. Soc. Dalton Trans. 773–777 (1989). doi:10.1039/DT9890000773

  31. Arena, G., Gianguzza, A., Pellerito, L., Musumeci, S., Purrello, R., Rizzarelli, E.: Co-ordination properties of dialkyltin(IV) in aqueous solution. Thermodynamics of complex formation with carboxylic acids. J. Chem. Soc. Dalton Trans. 2603–2608 (1990). doi:10.1039/DT9900002603

  32. Cucinotta, V., Gianguzza, A., Maccarrone, G., Pellerito, L., Purrello, R., Rizzarelli, E.: Thermodynamic and multinuclear magnetic resonance study of dimethyltin(IV) complexes with tridentate ligands in aqueous solution. J. Chem. Soc. Dalton Trans. 2299–2304 (1992). doi:10.1039/DT9920002299

  33. Tobias, R.S., Yasuda, M.: Studies on the soluble intermediates in the hydrolysis of dimethyltin dichloride. Can. J. Chem. 42, 781–791 (1964)

    Article  CAS  Google Scholar 

  34. De Stefano, C., Foti, C., Gianguzza, A., Martino, M., Pellerito, L., Sammartano, S.: Hydrolysis of (CH3)2Sn2+ in different ionic media: salt effects and complex formation. J. Chem. Eng. Data 41, 511–515 (1996)

    Article  Google Scholar 

  35. Lagrange, P., Schneider, M., Zare, K., Lagrange, J.: Determination and comparison of stability constants of uranium(VI) and vanadium(V) glycine complexes. Polyhedron 13, 861–867 (1994)

    Article  CAS  Google Scholar 

  36. Asso, M., Carpeni, G.: Recherches sur le point isohydrique et les équilibres acido–basiques de condensation ou association en chimie. XXVII. Les hydroxocomplexes des sels organostanniques (CH3)3SnCl et (C2H5)2SnCl2, en solutions aqueuses, à 25 °C et à différentes forces ionique. Can. J. Chem. 46, 1795–1802 (1968)

    Article  CAS  Google Scholar 

  37. Meloun, M., Javurek, M., Havel, J.: Multiparametric curve fitting. A structural classification of programs for analyzing multicomponent spectra and their use in equilibrium-model determination. Talanta 33, 51–524 (1986)

    Article  Google Scholar 

  38. Lockhart, T.P., Mandars, W.F.: Structure determination by NMR spectroscopy. Correlation of 2J(119Sn,1H) and the Me-Sn-Me angle in methyltin(IV) compounds. Inorg. Chem. 25, 892–895 (1986)

    Article  CAS  Google Scholar 

  39. Yang, Z., Bakas, T., Sanchez-Diaz, A., Charalampopoulos, C., Tsangaris, J., Hadjiliadis, N.: Interaction of Et2SnCl2 with 5′-IMP and 5′-GMP. J. Inorg. Biochem. 72(72), 133–140 (1998)

    Article  CAS  Google Scholar 

  40. Jankovics, H., Nagy, L., Buzas, N., Pellerito, L., Barbieri, R.: Coordination properties of adenosine-5′-monophosphate and related ligands towards Me2Sn(IV)2+ in aqueous solution. Inorg. Biochem. 92, 55–64 (2002)

    Article  CAS  Google Scholar 

  41. Beck, M.T., Nagypal, I.: Chemistry of Complex Equilibria. Ellis Harwood, New York (1990)

    Google Scholar 

  42. Farajtabar, A., Gharib, F., Jamaaat, P., Safari, N.: Complexation of 5,10,15,20-tetrakis(4-sulphonatophenyl)porphyrin with zinc(II) ions in aqueous solution. J. Chem. Eng. Data 53, 350–354 (2008)

    Article  CAS  Google Scholar 

  43. Gharib, F., Soleimani, F., Farajtabar, A., Aghaei, H.: Complexation of 5,10,15,20-tetrakis(4-sulphonatophenyl)porphyrin with the cadmium(II) ion at different ionic strengths. J. Chem. Eng. Data 54, 2060–2066 (2009)

    Article  CAS  Google Scholar 

  44. Jaberi, F., Gharib, F., Farajtabar, A.: Solute-solvent interaction effects on protonation and aggregation constants of TTMAPP in different aqueous solutions of methanol. J. Solution Chem. 42, 1559–1571 (2013)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Farrokh Gharib.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jaberi, F., Gharib, F. Spectrophotometric Determination of Equilibrium Constants of Dimethyl and Diethyltin(IV) Dichloride with 5,10,15,20-Tetrakis(4-trimethyl-ammonio-phenyl)-prophine Tetratosylate. J Solution Chem 44, 34–44 (2015). https://doi.org/10.1007/s10953-015-0290-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-015-0290-8

Keywords

Navigation