title: Sorption of ciprofloxacin and oxytetracycline zwitterions to soils and soil minerals: influence of compound structure.
abstract: Oxytetracycline (OTC) zwitterions sorbed to a greater extent than ciprofloxacin (CIP) zwitterions onto goethite and soils with moderate-to-low effective cation exchange capacities (ECEC < 10 cmol(c)/kg) because adjacent pairs of hydroxyl groups on the OTC molecule (absent in CIP) facilitated greater surface complexation to soil metal oxides and aluminosilicate edge sites. CIP sorbed to a higher extentthan OTC onto aluminosilicates and onto soils with "high" ECEC values (>10 cmol(c)/kg). The sorption of heterocyclic compounds structurally similar to CIP indicated that both positive charge localization on the cationic amine and the extent of charge delocalization to the heterocyclic ring influenced molecular orientation within the montmorillonite interlayers, van der Waals interactions, and the potential for sorption. The sorption of compounds structurally similar to OTC revealed that greater positive charge localization on the cationic amine facilitated sorption to montmorillonite, whereas ortho substituted anionic and cationic groups on a zwitterionic molecule resulted in unfavorable Coulombic interactions between the anionic moiety and the negatively charged surface and hindered sorption. Thus, greater CIP zwitterion sorption to aluminosilicates and "high" ECEC soils resulted from greater distance between the anionic and cationic groups, which maximized Coulombic attraction to the surface.
authors.affiliation: Department of Chemistry, Bowdoin College, Brunswick, Maine, USA.
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Carrasquillo
authors.forename: Gregory L
authors.initials: GL
authors.lastname: Bruland
authors.forename: Allison A
authors.initials: AA
authors.lastname: MacKay
authors.forename: Dharni
authors.initials: D
authors.lastname: Vasudevan
mesh_terms: D000327:Adsorption; D000538:Aluminum Silicates / Q000737:chemistry; D001546:Bentonite / Q000737:chemistry; D002939:Ciprofloxacin / Q000737:chemistry*; D000077215:Clay; D007700:Kinetics; D008903:Minerals / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry; D010118:Oxytetracycline / Q000737:chemistry*; D025341:Principal Component Analysis; D012987:Soil / Q000032:analysis*
chemical_list: D000538:Aluminum Silicates; D008903:Minerals; D010087:Oxides; D012987:Soil; D001546:Bentonite; D002939:Ciprofloxacin; D000077215:Clay; D010118:Oxytetracycline