Skip to main content
SpringerLink
Log in

Principles of Controlling the Correctness of Gas-Chromatographic Retention Indices of Previously Uncharacterized Analytes (Based on an Example of 2-Aryl-1,3-Dioxolanes and 2-Aryl-1,3-Dioxanes)

  • ARTICLES
  • Published:
Journal of Analytical Chemistry Aims and scope Submit manuscript

Abstract

The series of the interaction products of substituted benzaldehydes XC6H4CHO with several aliphatic diols (ethanediol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, and racemic 2,3-butanediol) were characterized for the first time by analytical parameters required for their chromatography–mass spectrometric identification: electron ionization mass spectra and gas-chromatographic retention indices (RIs) on a standard nonpolar polydimethylsiloxane stationary phase. It was found that it is expedient to combine this characterization of new compounds with controlling the correctness of the RIs by checking their correlations with data for one or several series of simpler and, therefore, characterized in more detail structural analogs. The proposed algorithm made it possible not only to confirm the correctness of all of the newly determined retention indices but also to reveal an erroneous reference value of the retention index of 4-ethoxyphenol. An appropriate selection of structural analogs provides an opportunity to use this method for controlling the retention indices of compounds in whose molecules steric interactions of structural fragments are manifested.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

Notes

  1. We would like to specially note that references to a database [1] in the text should not be considered as critical remarks. This database is among the most reliable ones, and one of the authors (I. Zenkevich) took part in the development of its chromatographic fragment in 1999–2018.

  2. The European version of this word is artefact, while the spelling artifact is used in the United States (and hence in the monograph by Middleditch [17].

REFERENCES

  1. The NIST 17 Mass Spectral Library (NIST17/2017/EPA/NIH). Software/Data Version (NIST17); NIST Standard Reference Database no.69, June 2017, Gaithersburg, MD: Natl. Inst. Standards Technol., 2017. http://webbook.nist.gov. Accessed Aprel 2020.

  2. Zenkevich, I.G. and Lukina, V.M., Analitika Kontrol’, 2019, vol. 23, no. 3, p. 410. https://doi.org/10.15826/analitika.2019.23.3.009

    Article  Google Scholar 

  3. Eliseenkov, E.V. and Zenkevich, I.G., Mass-Spektrom., 2020, vol. 20, no. 1, p. 40.

    Google Scholar 

  4. Zenkevich, I.G., J. Anal. Chem., 2020, vol. 75, no. 10, p. 1322.

    Article  CAS  Google Scholar 

  5. Zenkevich, I.G. and Fakhretdinova, L.N., Analitika Kontrol’, 2015, vol. 19, no. 2, p. 175. https://doi.org/10.15826/analitika.2015.19.2.013

    Article  Google Scholar 

  6. Zenkevich, I.G. and Fakhretdinova, L.N., J. Anal. Chem., 2016, vol. 71, no. 12, p. 1204. https://doi.org/10.7868/S004445021612015X

    Article  CAS  Google Scholar 

  7. Zenkevich, I.G., Babushok, V.I., Linstrom, P.J., White, E., and Stein, S.E., J. Chromatogr. A, 2009, vol. 1216, p. 6651. https://doi.org/10.1016/j.chroma.2009.07.065

    Article  CAS  PubMed  Google Scholar 

  8. Golovnya, R.V., Zhuravleva, I.L., Yakush, E.V., and Shenderjuk, V.V., J. Chromatogr. A, 1991, vol. 552, p. 1. https://doi.org/10.1016/S0021-9673(01)95709-7

    Article  CAS  Google Scholar 

  9. Misharina, T.A., Aerov, A.F., and Golovnya, R.V., J. Anal. Chem., 1990, vol. 45, no. 3, p. 382.

    Google Scholar 

  10. Misharina, T.A. and Golovnya, R.V., J. Anal. Chem., 1994, vol. 49, no. 4, p. 395.

    CAS  Google Scholar 

  11. Zenkevich, I.G., Kharicheva, E.M., and Kostikov, R.R., Russ. J. Org. Chem., 1999, vol. 35, no. 11, p. 1574.

    Google Scholar 

  12. Vazquez, A.M., Demmel, G.I., Criado, S.G., Aimar, M.L., Cantero, J., Rossi, L.I., and Velasco, M.I., Bol. Latinoam. Caribe Plant. Med. Aromat., 2011, vol. 10, no. 4, p. 351.

    CAS  Google Scholar 

  13. Tudor, E., J. Chromatogr. A, 1997, vol. 779, p. 287. https://doi.org/10.1016/S0021-9673(97)00453-6

    Article  CAS  Google Scholar 

  14. Tudor, E., Moldovan, D., and Zarna, N., Rev. Roum. Chem., 1999, vol. 44, no. 7, p. 665.

    CAS  Google Scholar 

  15. Liu, W., Wang, Y., Sun, M., Zhang, D., Zheng, M., and Yang, W., Chem. Commun., 2013, vol. 49, no. 54, p. 6042.

    Article  CAS  Google Scholar 

  16. Jafari, F. and Khodabakhshi, S., Org. Chem. Int., 2012, 475301. https://doi.org/10.1155/2012/475301

  17. Middleditch, B.S., Analytical Artifacts: GC, MS, HPLC, TLC, and PC, J. Chromatogr. Library, vol. 44, Amsterdam: Elsevier, 1989.

  18. Hamming, M.G. and Foster, N.G., Interpretation of Mass Spectra of Organic Compounds, New York: Academic, 1979.

    Google Scholar 

  19. Wulfson, N.S., Zaikin, V.G., and Mikaia, A.I., Mass-spektrometriya organicheskikh soedinenii (Mass Spectrometry of Organic Compounds), Moscow: Khimiya, 1986.

  20. Handbuch der Gaschromatographie, Leibnitz, E. and Struppe, H.G., Eds., Leipzig: Akademische Verlagsgesellschaft Geest & Portig K.-G., 1984, 3 ed.

    Google Scholar 

  21. Zenkevich, I.G., Todua, N.G., and Mikaia, A.I., Curr. Chromatogr., 2019, vol. 6, p. 3. https://doi.org/10.2174/2213240606666190709100858

    Article  CAS  Google Scholar 

  22. Zenkevich, I.G., J. Anal. Chem., 1999, vol. 54, no. 12, p. 1127.

    CAS  Google Scholar 

  23. Zenkevich, I.G., HRC & CC, J. High Resolut. Chromatogr. Chromatogr. Commun., 1998, vol. 21, no. 10, p. 565.

    Article  CAS  Google Scholar 

  24. Castello, G., J. Chromatogr. A, 1999, vol. 842, p. 51. https://doi.org/10.1016/S0021-9673(98)00989-3

    Article  CAS  Google Scholar 

  25. Schwartz, T.R., Petty, J.D., and Kaiser, E.M., Anal. Chem., 1983, vol. 55, p. 1839.

    Article  CAS  Google Scholar 

  26. Zenkevich, I.G., Russ. J. Org. Chem., 1992, vol. 29, no. 9, p. 1827.

    Google Scholar 

  27. Stein, S.E., Babushok, V.I., Brown, R.L., and Linstrom, P.J., J. Chem. Inf. Model., 2007, vol. 47, p. 975 .https://doi.org/10.1021/ci600548y

    Article  CAS  PubMed  Google Scholar 

Download references

ACKNOWLEDGMENTS

The experimental data discussed in this work were obtained using the equipment of the Chemistry Resource Center at the Institute of Chemistry, St. Petersburg State University. We are grateful to the staff members of the center for their assistance.

Funding

This work was supported in part by the Russian Foundation for Basic Research (grant no. 18-03-00151/a).

Author information

Authors and Affiliations

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

    I. G. Zenkevich & E. V. Eliseenkov

Authors
  1. I. G. Zenkevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Eliseenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. G. Zenkevich.

Additional information

Translated by V. Makhlyarchuk

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zenkevich, I.G., Eliseenkov, E.V. Principles of Controlling the Correctness of Gas-Chromatographic Retention Indices of Previously Uncharacterized Analytes (Based on an Example of 2-Aryl-1,3-Dioxolanes and 2-Aryl-1,3-Dioxanes). J Anal Chem 75, 1608–1625 (2020). https://doi.org/10.1134/S1061934820120151

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1061934820120151

Keywords:

Search

Navigation