bioaccumulation, sorption in soils, and nonspecific-toxicity reveals that ionic species
can actually be quite hydrophobic contrary to commonly held beliefs. Existing
models for the quantitative prediction of organic ions´ sorption in soils and biota
are quite restricted in their application range compared to neutral chemicals which is
due to the higher complexity of the various ionic sorption processes. In order to
further advance our understanding more high-quality sorption data are needed with a
focus on multivalent and zwitterionic ions in all partition systems as well as cations
in biological matrices.
Acknowledgements We thank Satoshi Endo and Beate Escher and an anonymous reviewer for
helpful comments.
Conflict of Interest On behalf of all authors, the corresponding author states that there is no
conflict of interest.
References
Abraham MH (2011) The permeation of neutral molecules, ions, and ionic species through
membranes: brain permeation as an example. J Pharm Sci 100(5):1690–1701. https://doi.org/
10.1002/jps.22404
Abraham MH, Acree JWE (2010a) The transfer of neutral molecules, ions and ionic species from
water to ethylene glycol and to propylene carbonate; descriptors for pyridinium cations. New J
Chem 34(10):2298–2305. https://doi.org/10.1039/C0NJ00222D
Abraham MH, Acree JWE (2010b) The transfer of neutral molecules, ions and ionic species from
water to wet octanol. Phys Chem Chem Phys 12(40):13182–13188. https://doi.org/10.1039/
C0CP00695E
Abraham MH, Acree WE (2010c) Equations for the transfer of neutral molecules and ionic species
from water to organic phases. J Org Chem 75(4):1006–1015. https://doi.org/10.1021/jo902388n
Abraham MH, Acree WE (2010d) Solute descriptors for phenoxide anions and their use to establish
correlations of rates of reaction of anions with iodomethane. J Org Chem 75(9):3021–3026.
https://doi.org/10.1021/jo100292j
Abraham MH, Acree WE Jr (2015) Analysis of the solubility of betaine: calculation of descriptors
and physicochemical properties. Fluid Phase Equilib 387:1–4. https://doi.org/10.1016/j.fluid.
2014.11.019
Abraham MH, Acree WE Jr (2016) Descriptors for ions and ion-pairs for use in linear free energy
relationships. J Chromatogr A 1430:2–14. https://doi.org/10.1016/j.chroma.2015.07.023
Armitage JM, Erickson RJ, Luckenbach T et al (2017) Assessing the bioaccumulation potential of
ionizable organic compounds: current knowledge and research priorities. Environ Toxicol
Chem 36(4):882–897. https://doi.org/10.1002/etc.3680
Austin RP, Davis AM, Manners CN (1995) Partitioning of ionizing molecules between aqueous
buffers and phospholipid vesicles. J Pharm Sci 84(10):1180–1183. https://doi.org/10.1002/jps.
2600841008
Avdeef A (2012) Absorption and drug development, 2nd edn. Wiley, Hoboken
Avdeef A, Box KJ, Comer JEA, Hibbert C, Tam KY (1998) pH-metric logP 10. Determination of
liposomal membrane-water partition coefficients of lonizable drugs. Pharm Res 15(2):209–215.
https://doi.org/10.1023/a:1011954332221
Bäuerlein PS, Mansell JE, ter Laak TL, de Voogt P (2011) Sorption behavior of charged and neutral
polar organic compounds on solid phase extraction materials: which functional group governs
sorption? Environ Sci Technol 46(2):954–961. https://doi.org/10.1021/es203404x
Environmental Sorption Behavior of Ionic and Ionizable Organic Chemicals
57
can actually be quite hydrophobic contrary to commonly held beliefs. Existing
models for the quantitative prediction of organic ions´ sorption in soils and biota
are quite restricted in their application range compared to neutral chemicals which is
due to the higher complexity of the various ionic sorption processes. In order to
further advance our understanding more high-quality sorption data are needed with a
focus on multivalent and zwitterionic ions in all partition systems as well as cations
in biological matrices.
Acknowledgements We thank Satoshi Endo and Beate Escher and an anonymous reviewer for
helpful comments.
Conflict of Interest On behalf of all authors, the corresponding author states that there is no
conflict of interest.
References
Abraham MH (2011) The permeation of neutral molecules, ions, and ionic species through
membranes: brain permeation as an example. J Pharm Sci 100(5):1690–1701. https://doi.org/
10.1002/jps.22404
Abraham MH, Acree JWE (2010a) The transfer of neutral molecules, ions and ionic species from
water to ethylene glycol and to propylene carbonate; descriptors for pyridinium cations. New J
Chem 34(10):2298–2305. https://doi.org/10.1039/C0NJ00222D
Abraham MH, Acree JWE (2010b) The transfer of neutral molecules, ions and ionic species from
water to wet octanol. Phys Chem Chem Phys 12(40):13182–13188. https://doi.org/10.1039/
C0CP00695E
Abraham MH, Acree WE (2010c) Equations for the transfer of neutral molecules and ionic species
from water to organic phases. J Org Chem 75(4):1006–1015. https://doi.org/10.1021/jo902388n
Abraham MH, Acree WE (2010d) Solute descriptors for phenoxide anions and their use to establish
correlations of rates of reaction of anions with iodomethane. J Org Chem 75(9):3021–3026.
https://doi.org/10.1021/jo100292j
Abraham MH, Acree WE Jr (2015) Analysis of the solubility of betaine: calculation of descriptors
and physicochemical properties. Fluid Phase Equilib 387:1–4. https://doi.org/10.1016/j.fluid.
2014.11.019
Abraham MH, Acree WE Jr (2016) Descriptors for ions and ion-pairs for use in linear free energy
relationships. J Chromatogr A 1430:2–14. https://doi.org/10.1016/j.chroma.2015.07.023
Armitage JM, Erickson RJ, Luckenbach T et al (2017) Assessing the bioaccumulation potential of
ionizable organic compounds: current knowledge and research priorities. Environ Toxicol
Chem 36(4):882–897. https://doi.org/10.1002/etc.3680
Austin RP, Davis AM, Manners CN (1995) Partitioning of ionizing molecules between aqueous
buffers and phospholipid vesicles. J Pharm Sci 84(10):1180–1183. https://doi.org/10.1002/jps.
2600841008
Avdeef A (2012) Absorption and drug development, 2nd edn. Wiley, Hoboken
Avdeef A, Box KJ, Comer JEA, Hibbert C, Tam KY (1998) pH-metric logP 10. Determination of
liposomal membrane-water partition coefficients of lonizable drugs. Pharm Res 15(2):209–215.
https://doi.org/10.1023/a:1011954332221
Bäuerlein PS, Mansell JE, ter Laak TL, de Voogt P (2011) Sorption behavior of charged and neutral
polar organic compounds on solid phase extraction materials: which functional group governs
sorption? Environ Sci Technol 46(2):954–961. https://doi.org/10.1021/es203404x
Environmental Sorption Behavior of Ionic and Ionizable Organic Chemicals
57