Absolute configuration of 2,2′,3,3′,6-pentachlorinatedbiphenyl (PCB 84) atropisomers

Xueshu Li, Sean R. Parkin, Hans Joachim Lehmler

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


Nineteen polychlorinated biphenyl (PCB) congeners, such as 2,2′,3,3′,6-pentachlorobiphenyl (PCB 84), display axial chirality because they form stable rotational isomers, or atropisomers, that are non-superimposable mirror images of each other. Although chiral PCBs undergo atropselective biotransformation and atropselectively alter biological processes, the absolute structure of only a few PCB atropisomers has been determined experimentally. To help close this knowledge gap, pure PCB 84 atropisomers were obtained by semi-preparative liquid chromatography with two serially connected Nucleodex β-PM columns. The absolute configuration of both atropisomers was determined by X-ray single-crystal diffraction. The PCB 84 atropisomer eluting first and second on the Nucleodex β-PM column correspond to (aR)-(−)-PCB 84 and (aS)-(+)-PCB 84, respectively. Enantioselective gas chromatographic analysis with the β-cyclodextrin-based CP-Chirasil-Dex CB gas chromatography column showed the same elution order as the Nucleodex β-PM column. Based on earlier reports, the atropisomers eluting first and second on the BGB-172 gas chromatography column are (aR)-(−)-PCB 84 and (aS)-(+)-PCB 84, respectively. An inversion of the elution order is observed on the Cyclosil-B gas chromatography and Cellulose-3 liquid chromatography columns. These results advance the interpretation of environmental and human biomonitoring as well as toxicological studies.

Original languageEnglish
Pages (from-to)16402-16410
Number of pages9
JournalEnvironmental Science and Pollution Research
Issue number17
StatePublished - Jun 1 2018

Bibliographical note

Publisher Copyright:
© 2017, Springer-Verlag Berlin Heidelberg.


  • Absolute configuration
  • Chirality
  • Enantiomer
  • Environmental contaminant
  • Polychlorinated biphenyl
  • Rotational isomer

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution
  • Health, Toxicology and Mutagenesis


Dive into the research topics of 'Absolute configuration of 2,2′,3,3′,6-pentachlorinatedbiphenyl (PCB 84) atropisomers'. Together they form a unique fingerprint.

Cite this