Abstract
Electron ionization mass spectra and gas chromatographic retention indices of a series of newly synthesized N-monosubstituted (alkyl, aryl, allyl) hydrazones of glyoxylic acid ethyl ester RNHN=CHCO2C2H5 were considered. It was shown the hydrazones were partially converted into isomeric (ethoxycarbonyl)methyl diimides during their GC separation (mostly in the heated injector port of the gas chromatograph). The retention indices of these diimides are lower than those of initial hydrazones by 268 ± 26 i.u. The most remarkable feature of these isomers appeared to be the high identity of their mass spectra because of similar rearrangements in molecular ions.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Zaikin, V. and Halket, J.M., A Handbook of Derivatives for Mass Spectrometry, Chichester: IM Publications, 2009.
Zenkevich, I.G., Carbonyls: derivatization for GC analysis, in Encyclopedia of Chromatography, Cazes, J., Ed., New York: Taylor and Francis, 2010, vol. 1.
Li, J., Feng, Y.L., Xie, C.J., Huang, J., Yu, J.Z., Feng, J.L., Sheng, G.Y., Fu, J.M., and Wua, M.H., Anal. Chim. Acta, 2009, vol. 635, no. 1, p. 83.
Lattova, E. and Perreault, H., Mass Spectrom. Rev., 2013, vol. 32, no. 5, p. 366.
Podgornaya, M.I., Nekhoroshev, S.A., Zenkevich, I.G., Isidorov, V.A., and Ioffe, B.V., Atlas mass-spektrov organicheskikh soedinenii (Mass Spectra of Organic Compounds: Atlas), vol. 1: Mass-spektry proizvodnykh gidrazina (Mass Spectra of Hydrazine Derivatives), Novosibirsk: Nauka, 1977.
Zenkevich, I.G., Isidorov, V.A., and Ioffe, B.V., Zh. Org. Khim., 1978, vol. 14, no. 7, p. 1362.
Zenkevich, I.G., Isidorov, V.A., and Ioffe, B.V., Zh. Org. Khim., 1980, vol. 16, no. 12, p. 2460.
Kelemen, J., Moss, S., Santer, H., and Winkler, T., Dyes Pigm., 1982, vol. 3, no. 1, p. 27.
Rotaru, K.I., Master’s Graduation Paper, St.-Petersburg: St.-Petersburg State Univ., 2015.
Lange, S.M., Tkachouk, E., Benitez, D., Lanfranchi, D.A., Elhabiri, M., Goddard, W.A., and Aprahamian, I., J. Am. Chem. Soc., 2011, vol. 133, no. 25, p. 9812.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © K.I. Rotaru, I.G. Zenkevich, R.R. Kostikov, 2015, published in Mass-spektrometriya, 2015, Vol. 12, No. 4, pp. 268–271.
Rights and permissions
About this article
Cite this article
Rotaru, K.I., Zenkevich, I.G. & Kostikov, R.R. GC/MS characterization of monosubstituted hydrazones of glyoxylic acid ethyl ester. J Anal Chem 71, 1377–1380 (2016). https://doi.org/10.1134/S1061934816140136
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1061934816140136