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Heptachlorepoxides: theoretical versus experimental study of the embedded samples in the matrixes of organic crystals

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Abstract

The analysis of heptachlorepoxides in gas- and condense phase of embedded in the organic matrixes analyte samples is highlighted. The electrospray ionization, matrix-assisted laser desorption/ionization (MALDI) mass spectrometry (MS), nuclear magnetic resonance, Raman and CD spectroscopy as well as quantum chemical methods are used. The competitive formation of the variety of epoxides, strongly depending of the reaction conditions. Thus, the products of interaction of matrix-analyte matrixes under the UV–MALDI–MS experiment are comprehensively examinated. Nonetheless, that for heptachlor (HA) is known an epoxide, existing in two isomeric forms, i.e. A and B (exo- and endo-one), the study on the mechanism of the epoxidation of HA, showed formation of new epoxides C–F and an intermediate (I), characterizing with high stability, decreasing in the raw F > A > C > B > I > D > E. The epoxide D appeared enantiomer of the insecticide oxychlodran. The reported results on the pesticides, their metabolites and decomposition reactivity products contributed significantly to the field of analytical chemistry, providing possibility for elaboration of highly selective protocols for assessment of environmental contaminant issues.

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Acknowledgments

The authors thank the Deutscher Akademischer Austausch Dienst (DAAD), the Deutsche Forschungsgemeinschaft (DFG), the central instrumental laboratories for structural analysis at Dortmund University (Germany) and the analytical and computational laboratory clusters at the Institute of Environmental Research (INFU) at the same University.

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  1. Institut für Umweltforschung, Fakultät für Chemie, Lehrstuhl für Analytische Chemie, Universität Dortmund, Otto-Hahn-Strasse 6, 44227, Dortmund, North Rheine-Westphalia, Germany

    Bojidarka Ivanova & Michael Spiteller

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  1. Bojidarka Ivanova
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  2. Michael Spiteller
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Correspondence to Bojidarka Ivanova.

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10847_2012_213_MOESM1_ESM.doc

Supplementary data CCDC < 775457, 881820 & 881821 > contained the supplementary crystallographic data for (1)–(3). These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk; Electronic absorption (resp. transmission) and infrared spectra of (1) – (3) (Figs. S1 and S2). (DOC 143 kb)

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Ivanova, B., Spiteller, M. Heptachlorepoxides: theoretical versus experimental study of the embedded samples in the matrixes of organic crystals. J Incl Phenom Macrocycl Chem 76, 415–426 (2013). https://doi.org/10.1007/s10847-012-0213-x

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