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Determination of the gas chromatographic elution sequences of the (+)- and (-)-enantiomers of stable atropistomeric PCBs on Chirasil-Dex
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
1996 (English)In: HRC Journal of High Resolution Chromatography, ISSN 0935-6304, E-ISSN 1521-4168, Vol. 19, no 7, 373-376 p.Article in journal (Refereed) Published
Abstract [en]

Pure enantiomers of chiral (atropisomeric) polychlorinated biphenyls (PCBs) obtained by high-performance liquid chromatography were used to establish the gas chromatographic elution sequences of the (+)- and (−)-enantiomers of six PCB atropisomers on Chirasil-Dex. The elution order was found to be (−/+) for PCBs 84, 132, 136, and 176 and (+/−) for PCBs 135 and 174. The retention characteristics of all 19 tri- and tetra-ortho atropisomeric PCBs were also investigated. Nine of the atropisomers could be separated using this chiral selector. PCBs 95, 132, and 149 were completely resovled and PCBs 84, 91, 135, 136, 174, and 176 were partially separated (R = 0.7–0.9). All of the separated congeners are 2,3,6-substituted in at least one ring, and conversely – none of the congeners that lacks 2,3,6-substitution could be separated. Thus, chiral recognition and enantiomer separation seems to be strongly governed by 2,3,6-substitution.

Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlagsgesellschaft, 1996. Vol. 19, no 7, 373-376 p.
Keyword [en]
enantioselective gas chromatography, stable atropisomeric polychlorinated biphenyls (PCBs), elution sequences, cyclodextrin derivatives, Chirasil-Dex
National Category
Analytical Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-5443DOI: 10.1002/jhrc.1240190703ISI: A1996VE01000002OAI: oai:DiVA.org:umu-5443DiVA: diva2:144958
Available from: 2002-01-25 Created: 2002-01-25 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Enantiospecific Analysis and Environmental Behavior of Chiral Persistent Organic Pollutants (POPs)
Open this publication in new window or tab >>Enantiospecific Analysis and Environmental Behavior of Chiral Persistent Organic Pollutants (POPs)
2002 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Many persistent organic pollutants (POPs) are chiral. These pollutants are generally released into the environment as racemates, but frequently undergo alterations in enantiomeric composition as soon as they are subjected to life chemistry processes. Enantiospecific analysis of chiral POPs is important since enantiomers of chiral compounds often exhibit differences in biological activity, and most biochemical processes in nature are stereospecific. For abiotic processes, such as air-water gas exchange, deposition and long-range air transport, enantiomeric patterns of POPs may be used as chemical markers.

The aim of the work described in this thesis was to improve our knowledge about the presence and fate of enantiomers of chiral POPs inthe environment to provide a sound basis for accurate risk assessment. The compounds included were organochlorine (OC) pesticides (α-HCH, chlordanes and o,p’-DDT), atropisomeric PCBs and some of their respective metabolites (heptachlor-exo-epoxide, oxychlordane and MeSO2-PCBs).

Analytical methods for chiral PCBs were developed, and the elution sequences of (+) and (−)-enantiomers were determined. Enantiomeric fraction (EF) was proposed as a better reflector of chiral composition than the conventional enantiomeric ratio (ER).

Enantioselective bioprocessing in various compartments was studied, with the main emphasis on factors controlling chiral composition in biota Correlations were detected between changes in EFs and differences in trophic levels. The changes were, however, not consistent for all compounds. Instead, the enantiomeric composition was found to be species-specific in the polar bear food chain and in aquatic species from the Baltic Sea. The EFs of some POPs in Baltic seals were related tonutritional status and biotransformation capacity.

Enantiomeric and isomeric patterns were used to investigate abiotic processes in the southern Baltic Sea environment and EFs were used tostudy soil as a source of atmospheric heptachlor-exo-epoxide.

Publisher
90 p.
Identifiers
urn:nbn:se:umu:diva-9 (URN)91-7305-162-4 (ISBN)
Public defence
(English)
Available from: 2002-01-25 Created: 2002-01-25 Last updated: 2012-06-28Bibliographically approved

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