On the thermally induced isomerisation of hexabromocyclododecane stereoisomers

Köppen, Robert; Becker, Roland; Jung, Christian; Nehls, Irene

doi:10.1016/j.chemosphere.2007.11.009

Cited by 88 publications

(49 citation statements)

References 16 publications

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“…The thermally induced interconversion of HBCD stereoisomers was first reported by Peled [8], confirmed later [9], and recently studied in detail [10,11]. It was shown experimentally that any given mixture of α-HBCD, β-HBCD, and γ-HBCD moves towards an equilibrium dominated by α-HBCD [8,9,10].…”

Section: The Isomerism Of Hbcd and The Interconversion Mechanismmentioning

confidence: 69%

“…The experimental set-up for the kinetic analysis of the isomerisation of HBCD is discussed in detail elsewhere [10]. In brief, pure (+)-γ-HBCD was exposed to 433 K for different periods between two and 60 minutes and the concentrations of all six stereoisomers ( Figure 1) were determined for each point in time by liquid chromatography with diode array detection and using a chiral column.…”

Section: Experimental Results Of the Interconversionmentioning

confidence: 99%

“…It was shown experimentally that any given mixture of α-HBCD, β-HBCD, and γ-HBCD moves towards an equilibrium dominated by α-HBCD [8,9,10]. Experiments with neat (+)-α-HBCD, (+)-β-HBCD, or (+)-γ-HBCD revealed that the reaction mixtures contain exclusively the six stereoisomers shown in Figure 1 [10] and that their isomerizations proceed as depicted in Figure 2. The mechanism of the transition between these structures is shown in Figure 3.…”

Section: The Isomerism Of Hbcd and The Interconversion Mechanismmentioning

confidence: 99%

“…The least squares fit of the experimental data corresponds to the following experimental (exp) rate matrix result: [10]. The corresponding time-dependent concentration plots are shown in Figure 5.…”

Section: Ir X ∈mentioning

confidence: 99%

“…The simulations are based on the Boltzmann distribution (canonical ensemble) of states which is the most likely distribution of states at constant temperature, constant number of particles, and constant volume. In order to compare simulations with experiments carried out with (+)-γ-HBCD [10] and since the interconversion only takes place in the liquid phase, the melting point of (+)-γ-HBCD at 433 K is the temperature of interest. However, the simulations were performed for the vacuum as a simplified approximation and the mutual interactions of the HBCD molecules in the liquid state were neglected.…”

Section: The Isomerism Of Hbcd and The Interconversion Mechanismmentioning

confidence: 99%

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Classical hybrid Monte-Carlo simulation of the interconversion of hexabromocyclododecane stereoisomers

Weber

Becker

Koeppen

et al. 2008

Molecular Simulation

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Section: The Isomerism Of Hbcd and The Interconversion Mechanismmentioning

confidence: 69%

Section: Experimental Results Of the Interconversionmentioning

confidence: 99%

Section: The Isomerism Of Hbcd and The Interconversion Mechanismmentioning

confidence: 99%

Section: Ir X ∈mentioning

confidence: 99%

Section: The Isomerism Of Hbcd and The Interconversion Mechanismmentioning

confidence: 99%

See 3 more Smart Citations

Classical hybrid Monte-Carlo simulation of the interconversion of hexabromocyclododecane stereoisomers

Weber

Becker

Koeppen

et al. 2008

Molecular Simulation

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Chiral Environmental Contaminants

Wong

Elmayergi

2009

Encyclopedia of Analytical Chemistry

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This article highlights techniques by which the enantiomers of chiral environmental pollutants can be separated and quantified. A large number of organic chemicals are chiral and exist as pairs of mirror images called enantiomers . These chemicals include legacy persistent organic pollutants (POPs) (e.g. polychlorinated biphenyls (PCBs)) and pesticides (e.g. dichlorodiphenyltrichloroethane (DDT)), as well as current‐use pesticides (e.g. pyrethroids), flame retardants (e.g. hexabromocyclododecane), and pharmaceuticals (e.g. ibuprofen). Understanding the environmental behavior of chiral xenobiotic compounds is important because enantiomers of a chiral compound may have different biological and toxicological effects, which must be delineated for accurate risk assessment of hazards, if any, posed by such chemicals. In addition, chiral chemicals are markers of biochemical activity in the environment, as enantiomer compositions are unaffected by physical and chemical processes but can change from differential enantiomer interactions with other chiral molecules (e.g. enzymes). For these reasons, the chirality of environmental pollutant occurrence, fate, and effects has been studied since the 1990s, when analytical capacity to measure chiral chemicals became widely available. We discuss major techniques for separating pollutant enantiomers including gas chromatography (GC), high‐performance liquid chromatography (HPLC), and capillary electrophoresis (CE). Enantioselective analytical separations are often coupled to mass spectrometry (MS) and tandem mass spectrometry (MS/MS) for quantification under environmentally relevant conditions (i.e. low concentrations to parts per trillion and below, in highly complex matrices such as wastewater and biological tissues). Issues involving sample preparation, data handling, and quality assurance/quality control are also described. Finally, we also illustrate applications of enantiomer‐specific measurements to gain insights into pollutants affecting environmental processes that could otherwise not be obtained, such as assessing pollutant biodegradation and delineating pollutant sources.

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Chirality as an Environmental Forensics Tool

Wong

Warner

2009

Persistent Organic Pollutants

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On the thermally induced isomerisation of hexabromocyclododecane stereoisomers

Cited by 88 publications

References 16 publications

Classical hybrid Monte-Carlo simulation of the interconversion of hexabromocyclododecane stereoisomers

Classical hybrid Monte-Carlo simulation of the interconversion of hexabromocyclododecane stereoisomers

Chiral Environmental Contaminants

Chirality as an Environmental Forensics Tool

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