Skip to main content
SpringerLink
Log in

The effect of carbonyl carbon atom replacement in acetone molecule (ACN) by sulfur atom (DMSO): Part II. Thermodynamic functions of complex formation of crown ethers with Na+ in mixed solvents

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

The thermodynamic functions of complex formation of benzo-15-crown-5 ether (B15C5) and sodium cation (Na+) in acetone–water mixtures at 298.15 K have been calculated. The equilibrium constants of B15C5/Na+ complex formation have been determined by conductivity measurements. The enthalpic effect of complex formation has been measured by the calorimetric method. The complexes are enthalpy-stabilized but entropy-destabilized in acetone–water mixtures. The effects of hydrophobic hydration, preferential solvation of B15C5 by a molecule of water and acetone, respectively and the solvation of Na+ on the complex formation processes have been discussed. The calculated thermodynamic functions of B15C5/Na+ complex formation and the effect of benzene ring on the complex formation have been compared with analogous data obtained in dimethylsulfoxide–water mixtures. The effect of carbonyl atom replacement in acetone molecule by sulphur atom (DMSO molecule) on the thermodynamic functions of complex formation has been analysed.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Jóźwiak M. The effect of carbonyl carbon atom replacement in acetone molecule (ACN) by sulfur atom (DMSO): the preferential solvation of cyclic ethers. J Therm Anal Calorim. 2008;93:701–5.

    Article  Google Scholar 

  2. van Unen DJ, Engbersen JFJ, Reinhoudt DN. Why do crown ethers activate enzymes in organic solvents? Biotechnol Bioeng. 2002;77:248–55.

    Article  Google Scholar 

  3. Fujii T, Nishizawa K. Isotope separations of potassium and rubidium in chemical exchange system with dicyclohexano-18-crown-6. J Radioannal Nucl Chem. 2001;249:569–71.

    Article  CAS  Google Scholar 

  4. Tsukube H, Yamada T, Shinoda S. Crown ether strategy toward chemical activation of biological protein functions. J Heterocycl Chem. 2001;38:1401–8.

    Article  CAS  Google Scholar 

  5. Brandt K, Kruszynski R, Bartczak TJ. AIDS-related lymphoma screen results and molecular structure determination of a new crown ether bearing aziridinylcyclophosphazene, potentially capable of ion-regulated DNA cleavage action. Inorg Chim Acta. 2001;322:138–44.

    Article  CAS  Google Scholar 

  6. Izatt RM, Bradshaw JS, Nielsen SA, Lamb JD, Christensen JJ. Thermodynamic and kinetic data for cation-macrocycle interaction. Chem Rev. 1985;85:271–339 and references there in.

    Google Scholar 

  7. Izatt RM, Pawlak K, Bradshaw JS. Thermodynamic and kinetic data for macrocycle interaction with cations and anions. Chem Rev. 1991;91:1721–2085 and references there in.

    Google Scholar 

  8. Izatt RM, Bradshaw JS, Pawlak K, Bruening RL, Tarbet BJ. Thermodynamic and kinetic data for macrocycle interaction with neutral molecules. Chem Rev. 1992;92:1261–354.

    Article  CAS  Google Scholar 

  9. Karkhaneei E, Afkhami A, Shamsipur M. Nuclear magnetic resonance studies of sodium ion complexes with several crown ethers in binary acetonitrile-dimethylsulfoxide mixtures. Polyhedron. 1996;15:1989–94.

    Article  CAS  Google Scholar 

  10. Karkhaneei E, Zebrajadian MH, Shamsipur M. Lithium-7 NMR study of several Li+-crown ether complexes in binary acetone-nitrobenzene mixtures. J Incl Phenom Mol Recognit Chem. 2001;40:309–12.

    Article  CAS  Google Scholar 

  11. Karkhaneei E, Zebarjadian MH, Shamsipur M. Complexation of Ba2+, Pb2+, Cd2+, and UO2 2+ ions with 18-crown-6 and dicyclohexyl-18-crown-6 in nitromethane and acetonitrile solutions by a competitive NMR technique using the 7Li nucleus as a probe. J Solut Chem. 2001;30:323–33.

    Article  CAS  Google Scholar 

  12. Rounaghi GH, Khazaee N, Sanavi KR. Study of complex formation between 18-crown-6 with Cu2+, Zn2+, Cd2+ and Pb2+ cations in some binary mixed non-aqueous solvents using the conductometric method. Pol J Chem. 2005;79:1143–53.

    CAS  Google Scholar 

  13. Rounaghi GH, Khoshnood RS, Zavvar MHA. Study of complex formation between N-phenylaza-15-crown-5 with Mg2+, Ca2+, Ag+ and Cd2+ metal cations in some binary mixed aqueous and non-aqueous solvents using conductometric method. J Incl Phenom Mol Recognit Chem. 2006;54:247–52.

    Article  CAS  Google Scholar 

  14. Rounaghi GH, Gerey GN, Kazemi MS. A conductometric study of complexation reactions between dibenzo-18-crown-6 (DB18C6) with Cu2+, Zn2+, Tl+ and Cd2+ metal cations in dimethylsulfoxide-ethylacetate binary mixtures. J Incl Phenom Mol Recognit Chem. 2006;55:167–72.

    Article  CAS  Google Scholar 

  15. Rounaghi GH, Soleamani A, Sanavi KR. Conductance studies on complex formation between aza-18-crown-6 with Ag+, Hg2+ and Pb2+ cations in DMSO-H2O binary solutions. J Incl Phenom Mol Recognit Chem. 2007;58:43–8.

    Article  CAS  Google Scholar 

  16. Gaber M, Rehab AF, Badr-Eldeen DF. Spectral and thermal studies of new Co(II) and Ni(II) hexaaza and octaaza macrocyclic complexes. J Therm Anal Calorim. 2008;91:957–62.

    Article  CAS  Google Scholar 

  17. Takeda Y, Tanaka M, Yamada H, Katsuta S. Stabilities and transfer activity coefficients from water to polar nonaqueous solvents of benzo-15-crown-5- and 15-crown-5-alkali metal ion complexes. J Coord Chem. 2002;55:459–68.

    Article  CAS  Google Scholar 

  18. Yudasheva LN, Hallwass F, da Cruz Goçalves SM, Simas AM, Krasilnikov OV. Anion influence on complex formation between 18-crown-6 and sodium ion in aqueous solutions. J Mol Liquids. 2003;106:31–41.

    Article  Google Scholar 

  19. Wu Y, Tabata M. Effects of solvent composition and temperature on K+-18-crown-6 complexation in acetonitrile-water mixed solvents. J Solut Chem. 2004;33:777–95.

    Article  CAS  Google Scholar 

  20. Rounaghi GH, Masroornia M, Ghaemi A, Rahchamani HA. Thermodynamic behaviour of complexation process between 15-crown-5 with Li+, Na+ and K+ cations in acetonitrile-water and 1-propanol-water binary media. Asian J Chem. 2007;19:1679–86.

    CAS  Google Scholar 

  21. Jóźwiak M. Complex formation of crown ethers with cations in the water-organic solvent mixtures. Part X. Thermodynamic of interactions between Na+ ion and 15-crown-5 ether in acetone-water mixtures at 298.15 K. J Mol Liquids. 2008;141:69–72.

    Article  Google Scholar 

  22. Piekarski H, Waliszewski D. Hydration effect on urea-non-electrolyte enthalpic pair interaction coefficients. dissolution enthalpies of urea in aqueous solution of alkoxyethanols at 298.15 K. Thermochim Acta. 1995;258:67–76.

    Article  CAS  Google Scholar 

  23. Jóźwiak M. Complex formation of crown ethers with cations in the water-organic solvent mixtures. Part VI. Thermodynamic of interactions of Na+ ion with benzo-15-crown-5 ether in the mixtures of water with N,N-dimethylformamide at 298.15 K. J Chem Thermodyn. 2004;36:299–308.

    Article  Google Scholar 

  24. Jóźwiak M. Thermochemical behaviour of crown ethers in the mixtures of water with organic solvents. Part VII. Enthalpy of solution of 15-crown-5 and benzo-15-crown-5 ethers in the mixtures of water with acetone at 298.15 K. Thermochim Acta. 2004;417:27–30.

    Article  Google Scholar 

  25. Barthel JM, Krienke H, Kunze W. Physical chemistry of electrolyte solutions. Modern aspects. Topics in physical chemistry, vol. 5. Darmstadt: Steinkopff/New York: Springer; 1988. 128 pp.

  26. Kratochvil B, Yeager HL. Conductance of electrolytes in organic solvents, topics in current chemistry 27. Berlin Heidelberg, New York: Springer-Verlag; 1972.

    Google Scholar 

  27. Buschmann HJ, Cleve E, Schollmeyer E. The complexation of alkaline cations by crown ethers and cryptands in acetone. J Solut Chem. 1994;23:569–77.

    Article  CAS  Google Scholar 

  28. Jóźwiak M, Piekarski H, Jóźwiak A. Thermodynamics of interactions of Na+ ion with 15-crown-5 ether in the mixtures of water with dimethylsulfoxide at 298.15 K. J Mol Liquids. 2003;106:15–29.

    Article  Google Scholar 

  29. Luo Q, Feng X, Shen M, Tu Q. Huaxue Xuebao. 1989;47:727–30. Paper cited in Izatt RM, Pawlak K, Bradshaw JS. Thermodynamic and kinetic data for macrocycle interaction with cations and anions. Chem Rev. 1991;91:1721–2085

    Google Scholar 

  30. Iglesias M, Orge B, Tojo J. Refractive indices, densities and excess properties on mixing of the systems acetone + methanol + water and acetone + methanol + 1-butanol at 298.15 K. Fluid Ph Equilibria. 1996;126:203–23.

    Article  CAS  Google Scholar 

  31. de Visser C, Heuvelsland WJM, Dunn LA, Somsen G. Some properties of binary aqueous liquid mixtures. Apparent molar volumes and heat capacities at 298.15 K over the whole mole fraction range. J Chem Soc Faraday Trans 1. 1978;74:1159–69.

    Article  Google Scholar 

  32. Löwen B, Schulz S. Excess molar enthalpies of acetone + water, cyclohexane, methanol, 1-propanol, 2-propanol, 1-butanol and 1-pentanol at 283.15, 298.15, 323.15, 343.15 and 363.15 K. Thermochim Acta. 1995;262:69–82.

    Article  Google Scholar 

  33. Fox MF, Whittingham KP. Component interactions in aqueous dimethyl sulphoxide. J Chem Soc Faraday Trans 1. 1975;71:1407–12.

    Article  CAS  Google Scholar 

  34. Poltoracki GM. Termodinamicheskie kharakteristiki nievodnykh rastvorov elektrolitov. Leningrad: Khimiya; 1984.

    Google Scholar 

  35. Izatt RM, Terry RE, Nelson DP, Chan Y, Eatough DJ, Bradshaw JS, et al. Calorimetric titration study of the interaction of some uni- and bivalent cations with benzo-15-crown-5, 18-crown-6, dibenzo-24-crown-8, and dibenzo-27-crown-9 in methanol-water solvents, at 25°C and μ = 0.1. J Am Chem Soc. 1976;98:7626–30.

    Article  CAS  Google Scholar 

  36. Jóźwiak M, Bald A, Wypych A. Complex formation of crown ethers with cations in the water-organic solvent mixtures. Part II. Thermodynamic of interactions of Na+ ion with benzo-15-crown-5 ether in the mixtures of water with dimethylsulfoxide at 298.15 K. J Mol Liquids. 2003;107:155–67.

    Article  Google Scholar 

  37. Jóźwiak M. Thermochemical behaviour of crown ethers in the mixtures of water with organic solvents. Part II. Enthalpy of solution of benzo-15-crown-5 ether in the mixtures of water with DMSO, DMF, DMA and HMPA at 298.15 K. J Mol Liquids. 1999;81:261–8.

    Article  Google Scholar 

  38. Jóźwiak M, Piekarski H. Heat of solution of 15-crown-5 ether in the mixtures of water with DMSO, DMF, DMA and HMPA at 298.15 K. J Mol Liquids. 1999;81:63–70.

    Article  Google Scholar 

Download references

Acknowledgement

This study was supported by Łódź University grant no. 505/676 (2005–2006) that is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Department of Physical Chemistry, University of Lodz, ul. Pomorska 165, 90-236, Lodz, Poland

    Małgorzata Jóźwiak

  2. Department of Physical Chemistry of Solutions, University of Lodz, ul. Pomorska 163, 90-236, Lodz, Poland

    Adam Bald

  3. Department of Organic Chemistry, University of Lodz, ul. Narutowicza 68, 90-136, Lodz, Poland

    Andrzej Jóźwiak

Authors
  1. Małgorzata Jóźwiak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Adam Bald
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Andrzej Jóźwiak
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Małgorzata Jóźwiak.

Additional information

For Part I, see Ref. [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jóźwiak, M., Bald, A. & Jóźwiak, A. The effect of carbonyl carbon atom replacement in acetone molecule (ACN) by sulfur atom (DMSO): Part II. Thermodynamic functions of complex formation of crown ethers with Na+ in mixed solvents. J Therm Anal Calorim 99, 307–314 (2010). https://doi.org/10.1007/s10973-009-0015-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-009-0015-6

Keywords

Search

Navigation