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Koeppen R, Becker R, Emmerling F, et al. Enantioselective preparative HPLC separation of the HBCD-Stereoisomers from the technical product and their absolute structure elucidation using X-ray crystallography. Chirality. 2007;19(3):214-22doi: 10.1002/chir.20366.
Koeppen, R., Becker, R., Emmerling, F., Jung, C., & Nehls, I. (2007). Enantioselective preparative HPLC separation of the HBCD-Stereoisomers from the technical product and their absolute structure elucidation using X-ray crystallography. Chirality, 19(3), 214-22. https://doi.org/10.1002/chir.20366
Koeppen, Robert, et al. "Enantioselective preparative HPLC separation of the HBCD-Stereoisomers from the technical product and their absolute structure elucidation using X-ray crystallography." Chirality vol. 19,3 (2007): 214-22. doi: https://doi.org/10.1002/chir.20366
Koeppen R, Becker R, Emmerling F, Jung C, Nehls I. Enantioselective preparative HPLC separation of the HBCD-Stereoisomers from the technical product and their absolute structure elucidation using X-ray crystallography. Chirality. 2007 Mar;19(3):214-22. doi: 10.1002/chir.20366. PMID: 17226748.
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Chirality. 2007 Mar;19(3):214-22. doi: 10.1002/chir.20366.

Enantioselective preparative HPLC separation of the HBCD-Stereoisomers from the technical product and their absolute structure elucidation using X-ray crystallography.

Chirality

Robert Koeppen, Roland Becker, Franziska Emmerling, Christian Jung, Irene Nehls

Affiliations

  1. Department of Analytical Chemistry, Reference Materials, Federal Institute for Materials Research and Testing (BAM), Berlin, Germany.

PMID: 17226748 DOI: 10.1002/chir.20366

Abstract

1,2,5,6,9,10-Hexabromocyclododecane (HBCD) is a widely used flame retardant, which tends to persist in the environment and accumulates in biota. The six stereoisomers (three racemates named alpha-, beta-, and gamma-HBCD) of the technical mixture were isolated with high-performance liquid chromatography (HPLC). Direct separations were performed on a chiral stationary phase containing permethylated beta-cyclodextrin (NUCLEODEX beta-PM column) and the pure enantiomers of alpha-, beta-, and gamma-HBCD were physically characterized for the first time. The absolute configurations of all six isomers were determined by anomalous dispersion using single crystal X-ray crystallography. Optical rotations alphaD in tetrahydrofuran were +4.2/-4.0 (alpha-HBCD), +26.1/-27.5 (beta-HBCD), and +68.0/-66.3 (gamma-HBCD). The sense of rotation could be correlated with the absolute configurations of alpha-, beta-, and gamma-HBCD enantiomers and their order of elution on a chiral permethylated beta-cyclodextrin-bonded stationary phase. The diastereomersalpha-, beta-, and gamma-HBCD displayed distinctly different melting points as well as (1)H-, (13)C NMR, and IR spectra.

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