title: Fragment-based approach to calculate hydrophobicity of anionic and nonionic surfactants derived from chromatographic retention on a C18stationary phase.
abstract: To predict the fate and potential effects of organic contaminants, information about their hydrophobicity is required. However, common parameters to describe the hydrophobicity of organic compounds (e.g., octanol-water partition constant [KOW]) proved to be inadequate for ionic and nonionic surfactants because of their surface-active properties. As an alternative approach to determine their hydrophobicity, the aim of the present study was therefore to measure the retention of a wide range of surfactants on a C18stationary phase. Capacity factors in pure water (k'0) increased linearly with increasing number of carbon atoms in the surfactant structure. Fragment contribution values were determined for each structural unit with multilinear regression, and the results were consistent with the expected influence of these fragments on the hydrophobicity of surfactants. Capacity factors of reference compounds and log KOWvalues from the literature were used to estimate log KOWvalues for surfactants (log KOWHPLC). These log KOWHPLC values were also compared to log KOWvalues calculated with 4 computational programs: KOWWIN, Marvin calculator, SPARC, and COSMOThermX. In conclusion, capacity factors from a C18stationary phase are found to better reflect hydrophobicity of surfactants than their KOWvalues. Environ Toxicol Chem 2017;36:329-336. © 2016 The Authors. Environmental Toxicology and Chemistry Published by Wiley Periodicals, Inc. on behalf of SETAC.
authors.affiliation: Institute for Risk Assessment Sciences, Utrecht University, Utrecht, The Netherlands.|Institute for Biodiversity and Ecosystem Dynamics, University of Amsterdam, Amsterdam, The Netherlands.
authors.forename: Jort
authors.initials: J
authors.lastname: Hammer
authors.affiliation: Institute for Risk Assessment Sciences, Utrecht University, Utrecht, The Netherlands.
authors.forename: Joris J-H
authors.initials: JJ
authors.lastname: Haftka
authors.affiliation: Institute for Risk Assessment Sciences, Utrecht University, Utrecht, The Netherlands.
authors.forename: Peter
authors.initials: P
authors.lastname: Scherpenisse
authors.affiliation: Institute for Risk Assessment Sciences, Utrecht University, Utrecht, The Netherlands.
authors.forename: Joop L M
authors.initials: JL
authors.lastname: Hermens
authors.affiliation: Institute for Biodiversity and Ecosystem Dynamics, University of Amsterdam, Amsterdam, The Netherlands.|KWR Watercycle Research Institute, Nieuwegein, The Netherlands.
authors.forename: Pim W P
authors.initials: PW
authors.lastname: de Voogt
mesh_terms: D000838:Anions; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D057927:Hydrophobic and Hydrophilic Interactions; D016014:Linear Models; D008956:Models, Chemical; D000442:Octanols / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D000838:Anions; D000442:Octanols; D013501:Surface-Active Agents; D014867:Water
keywords: Capacity factor; Chromatography; Octanol-water partition coefficient; Surface-active property