title: Dependence of GC-RRTs on the solvent-accessible surface area of dioxins and related compounds.
abstract: The correlation between gas chromatograph relative retention times (GC-RRTs) of dioxins and related compounds, polychlorinated biphenyls (PCBs), polychlorinated dibenzo-p-dioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), and polychlorinated naphthalenes (PCNs), and their solvent-accessible surface area (SAS) was analyzed for congeners and isomers. GC-RRTs were linearly dependent on SAS for congeners while there was little dependence for isomers. However, by using classification parameters, Nad-Cl, Nad-H, N1,9Cl, and NalphaCl, based on the substitution positions and patterns of chlorine and/or hydrogen atoms bound to the molecular skeleton, a linear relationship was found among isomers. Furthermore, the GC-RRTs of CDD, CDF, and CN isomers, which are planar, decreased despite increasing SAS, and this tendency was enhanced with the above classification. The retention behavior was explained in terms of the effective enhancement of molecular hydrophobicity caused by an increase in the number of adjacent chlorine pairs.
authors.affiliation: Institute for Environmental Sciences, University of Shizuoka, Yada, Japan. makinom@sea.u-shizuoka-ken.ac.jp
authors.forename: M
authors.initials: M
authors.lastname: Makino
mesh_terms: D001572:Benzofurans / Q000032:analysis / Q000737:chemistry*; D002849:Chromatography, Gas; D000072338:Dibenzofurans, Polychlorinated; D004784:Environmental Monitoring; D004785:Environmental Pollutants / Q000032:analysis*; D007536:Isomerism; D009281:Naphthalenes / Q000032:analysis / Q000737:chemistry*; D011078:Polychlorinated Biphenyls / Q000032:analysis / Q000737:chemistry*; D000072317:Polychlorinated Dibenzodioxins / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry*; D012016:Reference Values; D012989:Soil Pollutants / Q000032:analysis*; D012995:Solubility; D012997:Solvents / Q000737:chemistry
chemical_list: D001572:Benzofurans; D000072338:Dibenzofurans, Polychlorinated; D004785:Environmental Pollutants; D009281:Naphthalenes; D000072317:Polychlorinated Dibenzodioxins; D012989:Soil Pollutants; D012997:Solvents; D011078:Polychlorinated Biphenyls