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Solvent effect on protonation constants of salicylic acid in mixed aqueous organic solutions of DMSO

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Abstract

The first protonation constant of salicylic acid in water–DMSO solutions containing 0–50% (v/v) DMSO has been determined by spectrophotometric and potentiometric methods at 25 °C and an ionic strength of 0.1 M sodium perchlorate. The results indicate that the pK a value of salicylic acid increases with increasing proportion of DMSO in the mixed solvent. The variation of pK a value over the media composition range was explained by a linear solvation energy relationship, and correlations between pK a values and the Kamlet–Taft parameters α (hydrogen bond donor acidity), π* (dipolarity/polarizability), and β (hydrogen bond acceptor basicity), and the dielectric constant were calculated by means of multiple linear regression. The equations obtained can be used to estimate the first protonation constant of salicylic acid in a water–DMSO solvent from the relationship between the pK a values and the Kamlet–Taft parameters of the solvent. Also, the pK a value in aqueous medium was calculated by use of the SPARC online calculator and was compared with the value determined experimentally.

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Acknowledgments

The authors gratefully acknowledge financial support form the Research Council of Islamic Azad University Jouybar branch.

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Authors and Affiliations

  1. Department of Chemical Engineering, Islamic Azad University, Jouybar Branch, Jouybar, Iran

    Ali Farajtabar

  2. Chemistry Department, Faculty of Sciences, Shahid Beheshti University, Evin, Tehran, Iran

    Farrokh Gharib

Authors
  1. Ali Farajtabar
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  2. Farrokh Gharib
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Correspondence to Ali Farajtabar.

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Farajtabar, A., Gharib, F. Solvent effect on protonation constants of salicylic acid in mixed aqueous organic solutions of DMSO. Monatsh Chem 141, 381–386 (2010). https://doi.org/10.1007/s00706-010-0277-5

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  • DOI: https://doi.org/10.1007/s00706-010-0277-5

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