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The effect of carbonyl carbon atom replacement in acetone molecule (ACN) by sulfur atom (DMSO)

Part III. Effect of base–acid properties of the mixtures of water with acetone or dimethylsulfoxide on the solution enthalpy of cyclic ethers in mixed solvent

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Abstract

The enthalpies of solution of cyclic ethers: 1,4-dioxane, 12-crown-4 (12C4), and 18-crown-6 (18C6) in water–acetone mixtures have been measured within the whole mole fraction range at 298.15 K. Based on the obtained data, the effect of base–acid properties of water–acetone mixtures on the solution enthalpy of cyclic ethers in this mixed solvent has been analyzed. The strong dependence of the enthalpy of solution (solvation) of cyclic ethers on basic properties of mixed solvent has been observed. The effects of carbonyl atom replacement in acetone (ACN) molecule by sulfur atom (DMSO molecule) and base–acid properties of mixed solvent on the solvation process of cyclic ethers have been analyzed.

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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. Jóźwiak M. 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. doi:10.1007/s10973-009-0015-6.

  3. Meenakshisundaram S, Parthiban S, Bhagavannarayana G, Madhurambal G, Mojumda SC. Influence of organic solvent on tristhioureazinc(II)sulphate crystals. Therm Anal Calorim. 2009;96:125–9.

    Article  CAS  Google Scholar 

  4. Kamiyama T, Liu HL, Kiura T. Preferential solvation of lysozyme by dimethyl sulfoxide in binary solutions of water and dimethyl sulfoxide. J Therm Anal Calorim. 2009;95:353–9.

    Article  CAS  Google Scholar 

  5. Aki H, Ikeda H, Yukawa M, Iwase Y, Mibu N. Effect of pH on the formation of inclusion complexes between β-lactam antibiotics and 2-hydroxypropyl-β-cyclodextrin in aqueous solution. J Therm Anal Calorim. 2009;95:421–6.

    Article  CAS  Google Scholar 

  6. Marongiu B, Piras A, Porcedda S, Tuveri E. Thermodynamic properties of binary mixtures containing oxaalkanes. Part V. Monoethers, acetals, polyethers, cyclic mono- and di-ethers + benzene. J Therm Anal Calorim. 2009;95:149–59.

    Article  CAS  Google Scholar 

  7. Marcus Y. Preferential solvation in mixed solvents. Part. 11. Eight additional completely miscible aqueous co-solvent binary mixtures and the relationship between the volume-corrected preferential solvation parameters and structure of the co-solvents. Phys Chem Chem Phys. 2002;4:4462–71.

    Article  CAS  Google Scholar 

  8. 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 Phase Equilibria. 1996;126:203–23.

    Article  CAS  Google Scholar 

  9. 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 

  10. Lowen 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 

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

    Article  CAS  Google Scholar 

  12. Reichardt Ch. Solvatochromic dyes as solvent polarity indicators. Chem Rev. 1994;94:2319–58.

    Article  CAS  Google Scholar 

  13. Kamlet MJ, Taft RW. The solvatochromic comparison metod. I. The β-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc. 1976;98:377–83.

    Article  CAS  Google Scholar 

  14. Kamlet MJ, Abboud JLM, Abraham MH, Taft RW. Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α, and β, and some methods for simplifying the generalized solvatochromic equation. J Org Chem. 1983;48:2877–87.

    Article  CAS  Google Scholar 

  15. Piekarski H, Waliszewski D. Enthalpic pair interaction coefficients in DMF solution. 3. Thermochemistry of NaI solutions in mixtures of N,N-dimethyIformamide with urea, formamide, acetamide and N,N-dimethylacetamide at 298.15 K. J Thermal Anal. 1996;47:1639–47.

    Article  CAS  Google Scholar 

  16. 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 Thermodynamics. 2004;36:299–308.

    Article  Google Scholar 

  17. 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 mixures of water with acetone at 298.15 K. Thermochim Acta. 2004;417:27–30.

    Article  Google Scholar 

  18. Jóźwiak M. Thermochemical behaviour of crown ethers in the mixtures of water with organic solvents. Part V. Enthalpy of solution of 12-crown-4 and 18-crown-6 ethers in the mixtures of water with dimethylsulfoxide and N,N-dimethylformamide at 298.15 K. J Mol Liquids. 2003;107:169–83.

    Article  Google Scholar 

  19. 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 

  20. Krygowski TM, Wrona PK, Zielkowska U. Empirical parameters of Lewis acidity and basicity for aqueous binary solvent mixtures. Tetrahedron. 1985;41:4519–27.

    Article  CAS  Google Scholar 

  21. Jóźwiak M, Piekarski H. Thermochemical behaviour of crown ethers in aqueous organic solvents Part IV: propanol and acetonitrile with water mixtures. J Thermal Anal Calorim. 2002;69:291–300.

    Article  Google Scholar 

  22. Vinson CG, Martin JJ. Heat of vaporization and vapour pressure of 1, 4-dioxane. J Chem Eng Data. 1963;8:74–5.

    Article  CAS  Google Scholar 

  23. Briggner LE, Wadsö I. Some thermodynamic properties of crown ethers in aqueous solution. J Chem Thermodyn. 1990;22:143–8.

    Article  CAS  Google Scholar 

  24. Nichols G, Orf J, Reiter SM, Chickos J, Gokel GW. The vaporization enthalpies of some crown and polyethers by correlation gas chromatography. Thermochim Acta. 2000;346:15–28.

    Article  CAS  Google Scholar 

  25. Fawcett W, Krygowski TM. A complementary Lewis acid-base description of solvent effects II. Dipole-dipole interactions. Aust J Chem. 1975;28:2115–24.

    Article  CAS  Google Scholar 

  26. Kogel GW, Cram DJ, ChL Lotta, Harris HP, Cook FL. Preparation and purification of 18-crown-6[1,4,7,10,13,16-hexaoxacyclooctadecane]. J Org Chem. 1974;39:2445–6.

    Article  Google Scholar 

  27. Mosier-Boss PA, Popov AI. NMR and infrared studies of the complexation reaction of 18-crown-6 with some organic solvents. J Am Chem Soc. 1985;107:6168–74.

    Article  CAS  Google Scholar 

  28. Jóźwiak M. Thermochemical behaviour of crown ethers in the mixtures of water with organic solvents. Part IX. Effect of base-acid properties of (1 − x)AN + xH2O on the solution enthalpy of cyclic ethers in this mixed solvent at T = 298.15 K. J Chem Thermodynamics. 2009;41:522–4.

    Article  Google Scholar 

  29. Jóźwiak M. The effect of properties of water-organic solvent mixtures on the solvation enthalpy of of 12-crown-4, 15-crown-5, 18-crown-6 and benzo-15-crown-5 ethers at 298.15 K. Thermochim Acta. 2004;417:31–41.

    Article  Google Scholar 

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Acknowledgements

This study was supported by Łódź University Grant No. 505/676 (2006) that is gratefully acknowledged.

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Correspondence to Małgorzata Jóźwiak.

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The effect of carbonyl carbon atom replacement in acetone molecule (ACN) by sulfur atom (DMSO) Part III—Part I, ref. [1]; Part II [2].

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Jóźwiak, M. The effect of carbonyl carbon atom replacement in acetone molecule (ACN) by sulfur atom (DMSO). J Therm Anal Calorim 101, 1039–1045 (2010). https://doi.org/10.1007/s10973-009-0573-7

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  • DOI: https://doi.org/10.1007/s10973-009-0573-7

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