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Deduction of Physicochemical Properties from Solubilities: 2,4-Dihydroxybenzophenone, Biotin, and Caprolactam as Examples

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Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, U.K.
Department of Chemistry, University of North Texas, 1155 Union Circle Drive #305070, Denton, Texas 76203-5017, United States
Cite this: J. Chem. Eng. Data 2015, 60, 5, 1440–1446
Publication Date (Web):April 15, 2015
https://doi.org/10.1021/je501140p
Copyright © 2015 American Chemical Society

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    Abstract

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    Solubilities of 2,4-dihydroxybenzophenone have been measured at 298 K in 19 organic solvents. Combination with a known value of the solubility in water enables corresponding partition coefficients from water to these solvents to be deduced. It is shown that solubilities, via the partition coefficients, can yield the Abraham descriptors for 2,4-dihydroxybenzophenone, and that these, in turn, can be used to estimate a very large number of further solubilities, partition coefficients, and values of biological and environmental properties. This method of extracting information from solubilities is further illustrated using literature data on solubilities of biotin and of caprolactam.

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    Cited By

    This article is cited by 25 publications.

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    4. Emily Wu, Sneha Sinha, Chelsea Yang, Miles Zhang, William E. Acree. Abraham Solvation Parameter Model: Calculation of L Solute Descriptors for Large C11 to C42 Methylated Alkanes from Measured Gas–Liquid Chromatographic Retention Data. Liquids 2022, 2 (3) , 85-105. https://doi.org/10.3390/liquids2030007
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    15. Erin Hart, Megan Jodray, Karen Rodriguez, Maribel Barrera, Ellen Qian, Olivia Zha, Xin Y. Tong, Delani Woods, Yuqing Liu, Grace Lee, William E. Acree, Michael H. Abraham. Abraham model correlations for describing the solubilising character of 3-Methoxy-1-butanol and 1- tert -Butoxy-2-propanol solvents. Physics and Chemistry of Liquids 2019, 57 (2) , 163-173. https://doi.org/10.1080/00319104.2018.1432051
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    17. . Personal Care Products of Environmental Concern. 2018, 103-117. https://doi.org/10.1002/9781119312321.ch5
    18. Igor A. Sedov, Timur M. Salikov, Anisha Wadawadigi, Olivia Zha, Ellen Qian, William E. Acree, Michael H. Abraham. Abraham model correlations for describing the thermodynamic properties of solute transfer into pentyl acetate based on headspace chromatographic and solubility measurements. The Journal of Chemical Thermodynamics 2018, 124 , 133-140. https://doi.org/10.1016/j.jct.2018.05.003
    19. Igor A. Sedov, Timur M. Salikov, Diliara R. Khaibrakhmanova, Anisha Wadawadigi, Olivia Zha, Ellen Qian, Erin Hart, Maribel Barrera, William E. Acree, Michael H. Abraham. Determination of Abraham Model Correlations for Solute Transfer into Propyl Acetate Based on Experimental Activity Coefficient and Solubility Data. Journal of Solution Chemistry 2018, 47 (4) , 634-653. https://doi.org/10.1007/s10953-018-0743-y
    20. William E. Acree, Kaci R. Bowen, Melissa Y. Horton, Michael H. Abraham. Computation of Abraham model solute descriptors for 3-methyl-4-nitrobenzoic acid from measured solubility data. Physics and Chemistry of Liquids 2017, 55 (4) , 482-491. https://doi.org/10.1080/00319104.2016.1227813
    21. Bihan Jiang, Melissa Y. Horton, William E. Acree, Michael H. Abraham. Ion-specific equation coefficient version of the Abraham model for ionic liquid solvents: determination of coefficients for tributylethylphosphonium, 1-butyl-1-methylmorpholinium, 1-allyl-3-methylimidazolium and octyltriethylammonium cations. Physics and Chemistry of Liquids 2017, 55 (3) , 358-385. https://doi.org/10.1080/00319104.2016.1218009
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    23. Erin Hart, Ashley M. Ramirez, Sarah Cheeran, Maribel Barrera, Melissa Y. Horton, Anisha Wadawadigi, William E. Acree, Michael H. Abraham. Determination of Abraham model solute descriptors for 2-methyl-3-nitrobenzoic acid from measured solubility data in alcohol, alkyl ether, alkyl acetate and 2-alkoxyalcohol mono-solvents. Physics and Chemistry of Liquids 2017, 192 , 1-9. https://doi.org/10.1080/00319104.2017.1283692
    24. William E. Acree, Melissa Y. Horton, Elizabeth Higgins, Michael H. Abraham. Commentary on “Measurement and Correlation of the Solubility of Telmisartan (Form A) in Nine Different Solvents from 277.85 to 338.35 K”. Journal of Solution Chemistry 2016, 45 (12) , 1902-1905. https://doi.org/10.1007/s10953-016-0548-9
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