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Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids

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Abstract

The partition coefficients, P IL/w, of several compounds, some of them of biological and pharmacological interest, between water and room-temperature ionic liquids based on the imidazolium, pyridinium, and phosphonium cations, namely 1-octyl-3-methylimidazolium hexafluorophosphate, N-octylpyridinium tetrafluorophosphate, trihexyl(tetradecyl)phosphonium chloride, trihexyl(tetradecyl)phosphonium bromide, trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide, and trihexyl(tetradecyl)phosphonium dicyanamide, were accurately measured. In this way, we extended our database of partition coefficients in room-temperature ionic liquids previously reported. We employed the solvation parameter model with different probe molecules (the training set) to elucidate the chemical interactions involved in the partition process and discussed the most relevant differences among the three types of ionic liquids. The multiparametric equations obtained with the aforementioned model were used to predict the partition coefficients for compounds (the test set) not present in the training set, most being of biological and pharmacological interest. An excellent agreement between calculated and experimental log P IL/w values was obtained. Thus, the obtained equations can be used to predict, a priori, the extraction efficiency for any compound using these ionic liquids as extraction solvents in liquid-liquid extractions.

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Acknowledgments

Financial support from the Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) and Agencia Nacional de Promoción Científica y Técnica (ANPCYT) is gratefully acknowledged. M. Reta is a scientific member of CONICET and a Professor of Analytical Chemistry at the Universidad Nacional de La Plata (Argentina). J.M. Padró is a research fellow of CONICET, and R. Pellegrino Vidal is a research fellow of Comisión de Investigaciones Científicas de la Provincia de Buenos Aires (CIC-PBA), Argentina. The authors want to thank all of these scientific organizations.

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Authors and Affiliations

  1. Laboratorio de Investigación y Desarrollo de Métodos Analíticos (LIDMA), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 49 y 115, 1900, La Plata, Argentina

    Juan M. Padró, Rocío B. Pellegrino Vidal & Mario Reta

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  1. Juan M. Padró
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  2. Rocío B. Pellegrino Vidal
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  3. Mario Reta
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Correspondence to Mario Reta.

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Padró, J.M., Pellegrino Vidal, R.B. & Reta, M. Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids. Anal Bioanal Chem 406, 8021–8031 (2014). https://doi.org/10.1007/s00216-014-8264-z

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  • DOI: https://doi.org/10.1007/s00216-014-8264-z

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