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Related Concept Videos

Mass Spectrometry: Isotope Effect01:13

Mass Spectrometry: Isotope Effect

Most elements exist in nature as a mixture of isotopes. The isotopes differ in weight due to their respective number of neutrons. The molecular weight of a molecule is different depending on the specific isotope of its elements involved. As a result, the mass spectrum of the molecule exhibits peaks from the same fragment at multiple positions. The positions of these mass signals depend on the mass differences between isotopes. Furthermore, the intensity of these signals is dependent on the...
Mass Spectrometry: Alkyl Halide Fragmentation01:22

Mass Spectrometry: Alkyl Halide Fragmentation

Chlorine isotopes exist as 35Cl and 37Cl in a 3:1 ratio, while bromine isotopes exist as 79Br and 81Br in a 1:1 ratio. The mass spectrum of alkyl halides typically produces two distinct molecular ion peaks, the molecular ion peak, [M], and the molecular ion plus two, [M + 2] peak. The relative heights of these two peaks are proportional to the isotopic abundance ratios of the halide. For example, 2‐chloropropane and 1‐bromopropane display two peaks with relative peak heights in a 3:1 and 1:1...
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

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Baseline isotopic data of polyhalogenated compounds.

Walter Vetter1, Wolfgang Armbruster, Tatiana R Betson

  • 1University of Hohenheim, Institute of Food Chemistry, Garbenstr. 28, D-70593 Stuttgart, Germany. w-vetter@uni-hohenheim.de

Analytica Chimica Acta
|August 29, 2007
PubMed
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Stable isotope analysis using EA-IRMS revealed distinct isotopic signatures for polyhalogenated compounds. Differences in deuterium (2H) and carbon (13C) values helped trace the origins of pesticides like DDT and toxaphene.

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Area of Science:

  • Environmental Chemistry
  • Isotope Geochemistry
  • Organic Pollutant Analysis

Background:

  • Polyhalogenated compounds, including pesticides and their metabolites, are persistent environmental contaminants.
  • Understanding the sources and pathways of these compounds is crucial for environmental risk assessment.
  • Isotopic analysis offers a powerful tool for source apportionment and authentication of chemical products.

Purpose of the Study:

  • To determine the stable isotope ratios (delta2H and delta13C) of various polyhalogenated compounds.
  • To investigate the potential of isotopic analysis for differentiating between sources of these chemicals.
  • To explore the relationship between the degree of chlorination and isotopic composition in toxaphene-like compounds.

Main Methods:

  • Elemental Analysis-Isotope Ratio Mass Spectrometry (EA-IRMS) for delta2H and delta13C determination.
  • 2H Nuclear Magnetic Resonance (NMR) spectroscopy for quantifying 2H isotopomer abundances.
  • Controlled synthesis of chlorinated camphene derivatives to study isotopic changes during chlorination.

Main Results:

  • A wide range of delta2H (-235‰ to +75‰) and delta13C (-22‰ to -38‰) values were observed for compounds related to DDT, hexachlorocyclohexanes, toxaphene, bromophenols, and bromoanisoles.
  • No direct correlation was found between delta2H and delta13C values.
  • Isotopic analysis of 2,4-dibromophenol and 2,4-dibromoanisole indicated different origins for samples from various suppliers.
  • Synthesis experiments showed that increasing chlorination degree led to 2H enrichment in reaction products, and initial delta2H values of starting materials influenced the product's isotopic composition.

Conclusions:

  • Stable isotope analysis (delta2H and delta13C) is effective in characterizing polyhalogenated compounds and distinguishing their origins.
  • Isotopic variations in bromophenols and bromoanisoles suggest differential formation or degradation pathways.
  • The synthesis of toxaphene analogues demonstrates that isotopic composition is sensitive to both starting material and reaction conditions, providing insights into the formation of complex chlorinated mixtures.