title: Interactions of hydroxy-s-triazines with sodium dodecyl sulfate-micelles investigated by micellar capillary electrophoresis.
abstract: The electrophoretic behavior of fourteen 4,6-diamino-s-triazines was investigated in the presence of an anionic surfactant (sodium dodecyl sulfate, SDS) using micellar capillary electrophoresis (MCE). The measurements were performed at the pH of zero charge of the hydroxytriazines and the existence of strong ionic and H-bond interactions of hydroxy-s-triazine species with the anionic micelles could be shown. Their migration behavior was compared to the n-octanol-water partition coefficients (log Kow) measured with reverse-phase HPLC and calculated with different fragment contribution methods. A partition model was proposed to understand the interactions of the three major hydroxy-s-triazine species: cationic, anionic and neutral (presenting enol and keto forms) with the charged SDS micelles taken as model for charged natural polyelectrolytes like humic substances. These results strongly indicate that hydroxy-striazines are polarized in the presence of the charged micelles and that they are essentially present in their keto form in the micellar phase (and enol form in the water phase), confirming previous studies suggesting the presence of zwitterionic resonance structures at a neutral pH around their isoelectric point.
authors.affiliation: GSF-National Research Center for Environment and Health, Institute of Ecological Chemistry, Neuherberg, Germany.
authors.forename: D
authors.initials: D
authors.lastname: Freitag
authors.forename: P
authors.initials: P
authors.lastname: Schmitt-Kopplin
authors.forename: R
authors.initials: R
authors.lastname: Simon
authors.forename: A
authors.initials: A
authors.lastname: Kaune
authors.forename: A
authors.initials: A
authors.lastname: Kettrup
mesh_terms: D000465:Algorithms; D002851:Chromatography, High Pressure Liquid; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D019075:Electrophoresis, Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D008823:Micelles; D008958:Models, Molecular; D012967:Sodium Dodecyl Sulfate / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*
chemical_list: D008823:Micelles; D014227:Triazines; D012967:Sodium Dodecyl Sulfate