Hydrolytic Stability of Unsubstituted Hydrazones of Aromatic Carbonyl Compounds in Reversed-Phase HPLC

A. Deruish; Деруиш А.; G. V. Karakashev; Каракашев Г. В.; A. I. Ukolov; Уколов А. И.; I. G. Zenkevich; Зенкевич И. Г.

doi:10.31857/S0044450223020032

Hydrolytic Stability of Unsubstituted Hydrazones of Aromatic Carbonyl Compounds in Reversed-Phase HPLC

Authors: Deruish A.¹, Karakashev G.V.², Ukolov A.I.², Zenkevich I.G.¹
Affiliations:
1. Institute of Chemistry, St. Petersburg State University
2. Research Institute of Hygiene, Occupational Pathology, and Human Ecology, Federal Medical and Biological Agency of Russia
Issue: Vol 78, No 2 (2023)
Pages: 166-175
Section: ОРИГИНАЛЬНЫЕ СТАТЬИ
URL: https://journals.rcsi.science/0044-4502/article/view/136016
DOI: https://doi.org/10.31857/S0044450223020032
EDN: https://elibrary.ru/CEGSOJ
ID: 136016

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

Unsubstituted hydrazones RR′C=NNH2 are unstable during gas chromatographic separation. Testing of their resistance to hydrolysis under reversed-phase HPLC showed that aromatic ketone hydrazones are stable. In contrast, aldehyde hydrazones are only stable in neutral methanol–water systems (in the absence of acidic modifiers). In acetonitrile–water systems containing 0.1% of formic acid, only aromatic ketone hydrazones are stable, while aldehyde derivatives are completely hydrolyzed. This difference in stability must be taken into account in determining other compounds of these classes. To detect the hydrolysis of analytes, we compared the retention indices of the initial carbonyl compounds and hydrazones at different volume ratios of organic modifiers and aqueous phases and different pH values of the eluent, the relative absorbance values of the characterized components A(254/220) = A(254)/A(220), and the chromatography–mass spectrometric data.

Keywords

unsubstituted hydrazones of aromatic carbonyl compounds, reversed-phase high-performance, liquid chromatography, analyte instability upon separation

References

Zenkevich I.G. Features and new examples of gas chromatographic separation of thermally unstable analytes. Ch. 3 / Recent Advances in Gas Chromatography. London: IntechOpen Ltd., 2020. P. 1. https://doi.org/10.5772/intechopen.94229
Middleditch B.S. Analytical Artifacts: GC, MS, HPLC, TLC, and PC. Amsterdam: J. Chromatogr. Library, 1989. V. 44. 1033 p.
Herr C.H., Whitmore F.C., Schiessler R.W. The Wolff–Kishner reaction at atmospheric pressure // J. Am. Chem. Soc. 1945. V. 67. № 12. P. 2061. https://doi.org/10.1021/ja01228a002
Soffer M.D., Soffer M.B., Sherk K.W. A low pressure method for Wolff–Kishner reduction // J. Am. Chem. Soc. 1945. V. 67. № 9. P. 1435. https://doi.org/10.1021/ja1225a004
Kuethe J.T., Childers K.G., Peng Z., Journet M., Humphrey G.R., Vickery T., Bachert D., Lam T.T. A practical kilogram-scale implementation of the Wolff–Kishner reduction // Org. Process Res. Development. 2009. V. 13. № 3. P. 576. https://doi.org/10.1021/op9000274
The NIST Mass Spectral Library (NIST/EPA/NIH EI MS Library, 2017 Release). Software/Data Version; NIST Standard Reference Database, Number 69, August 2017. National Institute of Standards and Technology, Gaithersburg, MD 20899: http://webbook.nist.gov (дата обращения: апрель 2022 г.).
Зенкевич И.Г., Подольский Н.Е. Выявление соединений, нестабильных в условиях газохроматографического разделения. Незамещенные гидразоны карбонильных соединений // Аналитика и контроль. 2017. Т. 21. № 2. С. 125. https://doi.org/10.15825/analitika.2017.21.2.002
Зенкевич И.Г., Лукина В.М. Особенности газохроматографического разделения таутомеров этилацетоацетата // Журн. физ. химии. 2020. Т. 94. № 6. С. 910. https://doi.org/10.1134/S0036024420060357
Kornilova T.A., Ukolov A.I., Kostikov R.R., Zenkevich I.G. A simple criterion for gas chromatography/mass spectrometric analysis of thermally unstable compounds, and reassessment of the by-products of alkyl diazoacetate synthesis // Rapid Commun. Mass Spectrom. 2013. V. 27. № 3. P. 461. https://doi.org/10.1002/rcm.6457
Kovats’ retention index system / Encyclopedia of Chromatography / Ed. Cazes J. 3rd Ed. Boca Raton: CRC Press (Taylor & Francis Group), 2010. P. 1304.
Peterson M.L., Hirsch J. A calculation for locating the carrier gas front of a gas-liquid chromatogram // J. Lipid Res. 1959. V. 1. P. 132.
Kovarikova P., Vavrova K., Tomalova K., Schongut M., Hruskova K., Haskova P., Klimes J. HPLC-DAD and MS/MS analysis of novel drug candidates from the group of aromatic hydrazones revealing the presence of geometric isomers // J. Pharm. Biomed. Anal. 2008. V. 48. № 2. P. 295. https://doi.org/10.1016/j.jpba.2007.12.017
Isenberg S.L., Carter M.D., Crow B.S., Graham L.A., Johnson D.J., Beninato N., Steele K., Thomas J.D., Johnson R.C. Quantification of hydrazine in human urine by HPLC-MS-MS // J. Anal. Toxicol. 2016. V. 40. № 4. P. 248. https://doi.org/10.1093/jat/bkw015
Song L., Gao D., Li S., Wang Y., Liu H., Jiang Y. Simultaneous quantitation of hydrazine and acetylhydrazine in human plasma by high performance liquid chromatography – tandem mass spectrometry after derivatization with p-tolualdehyde // J. Chromatogr. B. 2017. V. 1063. P. 189. https://doi.org/10.1016/j.jchromb.2017.08.-36
Brewer C.T., Yang L., Edwards A., Lu Y., Low J., Wu J., Lee R.E., Chen T. The isoniazid metabolites hydrazine and pyridoxal isonicotinoyl hydrazone modulate heme biosynthesis // Toxicol. Sci. 2019. V. 168. № 1. P. 209. https://doi.org/10.1093/toxsci/kfy294
Wahbeh J., Milkowski S. The use of hydrazones for biomedical applications // SLAS Technol. 2019. V. 24. № 2. P. 161. https://doi.org/10.1117/2472630318822713
Mateeva A., Peikova L., Kondeva-Burdina M., Georgieva M. Development of new HPLC method for identification of metabolic degradation of N-pyrrolylhydrazide hydrazones with determined MAO-B activity in cellular cultures // Pharmacia. 2021. V. 69. № 1. P. 15. https://doi.org/10.3897/pharmacia.69.e78417
Derivatization of analytes in chromatography: General aspects / Encyclopedia of Chromatography / Ed. Cazes J. 3rd Ed. New York: Taylor & Francis, 2010. V. 1. P. 562.
Carbonyls: Derivatization for GC analysis / Encyclopedia of Chromatography / Ed. Cazes J. 3rd Ed. New York: Taylor & Francis, 2010. V. 1. P. 310.
Grosjean E., Green P.G., Grosjean D. Liquid chromatography analysis of carbonyl (2,4-dinitrophenyl)hydrazones with detection by diode array ultraviolet spectroscopy and by atmospheric pressure negative chemical ionization mass spectrometry // Anal. Chem. 1999. V. 71. № 9. P. 1851. https://doi.org/10.1021/ac981022v
Rapid separation and identification of carbonyl compounds by HPLC / Agilent Application Note / Wilmington: Agilent Technologies, Inc., 2008. 4 p.
Ochs S.M., Fasciotti M., Netto A.D.P. Analysis of 31 hydrazones of carbonyl compounds by RRLC-UV and RRLC-MS(/MS): A comparison of methods // J. Spectrosc. 2015. Article ID 890836. https://doi.org/10.1155/2015/890836
Damanik M., Murkovic M. Formation of potentially toxic carbonyl compounds during oxidation of triolein in the presence of alimentary antioxidants // Monatsh Chem. 2017. V. 148. № 12. P. 2031. https://doi.org/10.1007/s00706-017-2036-3
Frey J., Schneider F., Schink B., Hunn T. Synthesis of short-chain hydroxyaldehydes and their 2,4-dinitrophenylhydrazones derivatives, and separation of their isomers by high-performance liquid chromatography // J. Chromatogr. A. 2018. V. 1531. P. 143. https://doi.org/10.1016/chroma.2017.11.046
Kalia J., Reines R.T. Hydrolytic stability of hydrazones and oximes // Angew. Chem. Int. Ed. 2008. V. 47. № 39. P. 7523. https://doi.org/10.002/anie.200802651
Зенкевич И.Г., Косман В.М. Относительное поглощение при разных длинах волн - дополнительный УФ-спектральный параметр для идентификации органических соединений в обращенно-фазовой ВЭЖХ // Журн. аналит. химии. 1996. Т. 51. № 8. С. 870.
Зенкевич И.Г., Косман В.М. Новые возможности идентификации органических соединений по УФ-спектрам с использованием относительных оптических плотностей // Журн. прикл. химии. 1997. Т. 70. № 11. С. 1861
Зенкевич И.Г., Деруиш А. Аналитические аспекты зависимости индексов удерживания органических соединений в обращенно-фазовой ВЭЖХ от содержания метанола в составе элюента // Аналитика и контроль. 2022. Т. 26. № 1. С. 41. https://doi.org/10.15826/analitika.2022.26.1.004
Practical Gas Chromatography / Eds. Engewald W., Dettmer-Wilde K. Berlin: Springer-Verlag, 2014. 902 p.
Иоффе Б.В., Кузнецов М.А., Потехин А.А. Химия органических производных гидразина. Л.: Химия, 1979, 224 с.