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A New Concept Linking Observable Stable Isotope Fractionation to Transformation Pathways of Organic Pollutants
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    A New Concept Linking Observable Stable Isotope Fractionation to Transformation Pathways of Organic Pollutants
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    Swiss Federal Institute for Environmental Science and Technology (EAWAG) and Swiss Federal Institute of Technology Zurich (ETHZ), Ueberlandstrasse 133, CH-8600 Duebendorf, Switzerland, and Centre of Hydrogeology, University of Neuchâtel, Rue Emile Argand 11, CH-2007 Neuchâtel, Switzerland
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    Environmental Science & Technology

    Cite this: Environ. Sci. Technol. 2005, 39, 18, 6896–6916
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    https://doi.org/10.1021/es0504587
    Published August 4, 2005
    Copyright © 2005 American Chemical Society

    Abstract

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    Measuring stable isotope fractionation of carbon, hydrogen, and other elements by Compound Specific Isotope Analysis (CSIA) is a new, innovative approach to assess organic pollutant degradation in the environment. Central to this concept is the Rayleigh equation which relates degradation-induced decreases in concentrations directly to concomitant changes in bulk (= average over the whole compound) isotope ratios. The extent of in situ transformation may therefore be inferred from measured isotope ratios in field samples, provided that an appropriate enrichment factor (εbulk) is known. This εbulk value, however, is usually only valid for a specific compound and for specific degradation conditions. Therefore, a direct comparison of εbulk values for different compounds and for different types of reactions has in general not been feasible. In addition, it is often uncertain how robust and reproducible εbulk values are and how confidently they can be used to quantify contaminant degradation in the field. To improve this situation and to achieve a more in-depth understanding, this critical review aims to relate fundamental insight about kinetic isotope effects (KIE) found in the physico(bio)chemical literature to apparent kinetic isotope effects (AKIE) derived from εbulk values reported in environmentally oriented studies. Starting from basic rate laws, a quite general derivation of the Rayleigh equation is given, resulting in a novel set of simple equations that take into account the effects of (1) nonreacting positions and (2) intramolecular competition and that lead to position-specific AKIE values rather than bulk enrichment factors. Reevaluation of existing εbulk literature values result in consistent ranges of AKIE values that generally are in good agreement with previously published data in the (bio)chemical literature and are typical of certain degradation reactions (subscripts C and H indicate values for carbon and hydrogen):  AKIEC = 1.01−1.03 and AKIEH = 2−23 for oxidation of C−H bonds; AKIEC = 1.03−1.07 for SN2-reactions; AKIEC = 1.02−1.03 for reductive cleavage of C−Cl bonds; AKIEC = 1.00−1.01 for CC bond epoxidation; AKIEC = 1.02−1.03 for CC bond oxidation by permanganate. Hence, the evaluation scheme presented bridges a gap between basic and environmental (bio)chemistry and provides insight into factors that control the magnitude of bulk isotope fractionation factors. It also serves as a basis to identify degradation pathways using isotope data. It is shown how such an analysis may be even possible in complex field situations and/or in cases where AKIE values are smaller than intrinsic KIE values, provided that isotope fractionation is measured for two elements simultaneously (“two-dimensional isotope analysis”). Finally, the procedure is used (1) to point out the possibility of estimating approximate εbulk values for new compounds and (2) to discuss the moderate, but non-negligible variability that may quite generally be associated with εbulk values. Future research is suggested to better understand and take into account the various factors that may cause such variability.

    Copyright © 2005 American Chemical Society

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     Corresponding author phone:  ++1 416 978 0825; fax:  ++1 416 978 3938; e-mail:  [email protected]. Present address:  Stable Isotope Laboratory, Department of Geology, University of Toronto, 22 Russell Street, Toronto, Ontario M5S 3B1, Canada.

     EAWAG and ETHZ.

     Present address:  Centre de Recherche Public Henri Tudor, Centre de Ressources des Technologies de l'Environnement (CRTE), Technoport Schlassgoart, 66, rue de Luxembourg, B.P. 144, L-4002 Esch-sur-Alzette, Luxembourg.

    §

     University of Neuchâtel.

    Supporting Information Available

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    Experimental determination of isotope ratios; background information related to the rules of thumb; kinetic isotope effects reported in the literature (continued); mathematical derivation of the novel evaluation procedure; mathematical derivation of the approximate eqs 16 and 22 and illustration of associated errors; influence of a nonstatistical isotope distribution inside organic compounds; and reevaluation of original data on aerobic MTBE degradation of Hunkeler et al. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: Environ. Sci. Technol. 2005, 39, 18, 6896–6916
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