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Characterization of Substituted 1,3-Dioxolanes and 1,3-Dioxanes by Gas Chromatography–Mass Spectrometry

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Abstract

Until recently, one of the reasons for the unsatisfactory characterization of alicyclic ketals of aliphatic and alkylaromatic ketones was the absence of any mention of the presence of such compounds in natural samples. Another reason is in the low yields of such ketals on the interaction of ketones and diols under the conditions of conventional acid catalysis. To optimize the synthesis of trace amounts of such ketals, we used cobalt(II) bromide and dimethyl glyoxime as catalysts. The simplest chromatographic parameters, including the difference between the retention indices of the products and the starting compounds (difference in retention indices, DRI), are effective for identifying the target ketals in reaction mixtures. Such combined chromatography–mass spectrometric characteristics as homologous increments of retention indices (iRI) are informative not only for the group identification of analytes (assignment to the corresponding homologous series) and the assessment of their molecular weights (at low-intense signals of molecular ions). They are also useful for the determination of the total number of branches of the sp3-carbon skeleton of molecules (N) using the regression of N ≈ aiRI + b.

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Notes

  1. In the NIST database [1], medians of the mean values and their standard deviations and ranges, rather than mean values, are given to characterize the data samples.

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ACKNOWLEDGMENTS

The study is carried out using the equipment of the Resource Center in the field of “Chemistry” at the Institute of Chemistry, St. Petersburg State University. The authors are grateful to all colleagues working at the Center for assistance.

Funding

This work was supported by the Russian Foundation for Basic Research, grant no. 18-03-001512a for the Institute of Chemistry, St. Petersburg State University.

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Authors and Affiliations

  1. Institute of Chemistry, St. Petersburg State University, 198504, St. Petersburg, Russia

    E. V. Eliseenkov & I. G. Zenkevich

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  1. E. V. Eliseenkov
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  2. I. G. Zenkevich
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Correspondence to I. G. Zenkevich.

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Translated by O. Zhukova

ADDITIONAL INFORMATION

I.G. Zenkevich: ORCID ID 0000-0001-8975-2257.

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Eliseenkov, E.V., Zenkevich, I.G. Characterization of Substituted 1,3-Dioxolanes and 1,3-Dioxanes by Gas Chromatography–Mass Spectrometry. J Anal Chem 75, 1790–1807 (2020). https://doi.org/10.1134/S1061934820140087

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  • DOI: https://doi.org/10.1134/S1061934820140087

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