Abstract
General scheme of fragmentation of monofunctional organic compounds RX (R, alkyl and X, functional group) has been elucidated basing on analysis of mass spectra under conditions of electron impact. The mass spectra have been considered as superposition of a few peaks of characteristic ions containing group X or its fragments and the peaks of hydrocarbon ions (hydrocarbon subspectra). The hydrocarbon subspectrum analysis has allowed interpretation of the fragmentation processes forming the RX compounds mass spectra and estimation of contribution of each process into the total ion current. The possibility of simulating the spectra of non-studied compounds RX via the transformation of available mass spectra of RX compounds with the same alkyl fragment is discussed.
Similar content being viewed by others
References
Lebedev, A.T., Mass-spektrometriya v organicheskoi khimii (Mass Spectrometry in Organic Chemistry), Moscow: BINOM, 2003.
Silverstein, R.M., Webster, F.X., and Kiemle, D., Spectrometric Identification of Organic Compounds, New York: Wiley, 2005.
Vul’fson, N.S., Zaikin, V.G., and Mikaya, A.I., Mass-spektrometriya organicheskikh soedinenii (Mass Spectrometry of Organic Compounds), Moscow: Khimiya, 1986.
Chapman, J.R., Practical Organic Mass Spectrometry, New York: Wiley Interscience, 1985.
Polyakova, A.A., Molekulyarnyi mass-spektral’nyi analiz organicheskikh soedinenii (Molecular Mass Spectral Analysis of Organic Compounds), Moscow: Khimiya, 1983.
Zaikin, V.G. and Mikaya, A.A., Khimicheskie metody v mass-spektrometrii organicheskikh soedinenii (Chemical Methods of Mass Spectrometry in Organic Compounds), Moscow: Nauka, 1987.
Zaikin, V.G., Varlamov, A.A., Mikaya, A.A., and Prostakov, N.S., Osnovy mass-spektrometrii organicheskikh soedinenii (Bases Mass Spectrometry of Organic Compounds), Moscow: MAIK, 2001.
Zenkevich, I.G. and Ioffe, B.V., Interpretatsiya mass-spektrov organicheskikh soedinenii (The Interpretation of the Mass Spectra of Organic Compounds), Leningrad: Khimiya, 1986.
Johnstone, R., Mass Spectrometry for Organic Chemists, London: Cambridge University Press, 1972.
Bieman, K., Mass Spectrometry. Organic Chemical Applications, New York: McGraw Hill, 1962.
Benz, W., Massenspectrometrie Organishen Verbindungen, Leipzig: Akademische Verlagsgesellschaft, 1969.
Takhistov, V.V., Prakticheskaya mass-spektrometriya organicheskikh soedinenii (Practical Mass Spectrometry of Organic Compounds), Leningrad: Leningrad. Gos. Univ., 1977.
Takhistov, V.V., Organicheskaya mass-spektrometriya (Organic Mass Spectrometry), Leningrad: Nauka, 1990.
Takhistov, V.V. and Ponomarev, D.A., Organicheskaya mass-spektrometriya (Organic Mass Spectrometry), St. Petersburg: VVM, 2005.
Lebedev, A.T., Morozik, Yu.I., Myasoedov, B.F., Rybal’chenko, I.V., and Fomenko, P.V., Mass-Spektrometriya, 2007, vol. 4, no. 4, p. 255.
Morozik, Yu.I. and Smirnov, A.O., Mass-Spektrometriya, 2008, vol. 5, no. 3, p. 211.
Morozik, Yu.I., Smirnov, O.A., and Galyaev, G.V., Russ. J. Gen. Chem., 2011, vol. 81, no. 10, p. 2088. DOI: 10.1134/s1070363211100082.
Morozik, Yu.I., Galyaev, G.V., and Smirnov, O.A., J. Anal. Chem., 2011, vol. 66, no. 13, p 53. DOI: 10.1134/s1061934811130089.
NIST Mass Spectral Search Program for the NIST/EPA/NIH Mass Spectral Library, Version 2.0, 2005.
Nekrasov, Yu.S., Sukharev, Yu.N., Tepfer, E.E., and Molgachev, N.S., Izv. Akad. Nauk, Ser. Khim., 1996, no. 11, p. 2683.
Green, M.M., Tetrahedron, 1980, vol. 36, p. 2687. DOI: 10.1016/0040-4020(80)80144-x.
Budzikevich, G.B., Jerassi, K., and Williams, D., Interpretatsiya mass-spektrov organicheskikh soedinenii (The Interpretation of the Mass Spectra of Organic Compounds), Moscow: Mir, 1966.
Pritzkow, W., Theoretische Gesichtspunkte in der organishen Chemie, Dresden; Leipzig: Verlag von Theodor Steinkopf, 1963.
Carey, F.A. and Sundberg, R.J., Advanced Organic Chemistry, Moscow: Khimiya, 1981.
Palm, V.A., The Fundamentals of Quantitative Theory of Organic Reactions, Leningrad: Khimia, 1981.
Takhistov, V.V., Rodin, A.A., and Maksimova, B.N., Russ. Chem. Rev., 1991, vol. 60, no. 10, p. 1101.
Lebedev, A.T., Lebedev, K.S., Myasoedov, B.F., Rybal’chenko, I.V., Sigeikin, G.I., and Suvorkin, V.N., Mass-Spektrometriya, 2006, vol. 3, no. 4, p. 277.
Kireev, A.F., Rybal’chenko, I.V., Savchuk, V.I., Suvorkin, V.N., Tipukhov, V.N., and Khamidi, B.A., Zh. Analit. Khim., 2000, vol. 57, p. 842.
Kireev, A.F., Rybal’chenko, I.V., Savchuk, V.I., Suvorkin, V.N., and Kholstov, V.I., Zh. Analit. Khim., 2000, vol. 55, p. 933.
Samokhin, A.S., Cand. Sci. (Chem.) Dissertation, Moscow, 2013.
Samokhin, A.S., Sotnezova, K.M., and Revel’skii, I.A., Abstracts of Papers, V Vseross. konf. s mezhdunar. uchastiem “Mass-spektrometrija i ee prikladnye problemy” (V All-Russia. Conf. with Int. Participation “Mass Spectrometry and Its Application Problems”), Moscow, 2013, p. 28.
Bentley, T.W., and Johnstone, R.A.W., Advances in Physical Organic Chemistry. Mechanism and Structure in Mass Spectrometry, New York: Academic Press, 1970.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © Yu.V. Tkachuk, Yu.I. Morozik, A.V. Dudkin, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 3, pp. 390–402.
Rights and permissions
About this article
Cite this article
Tkachuk, Y.V., Morozik, Y.I. & Dudkin, A.V. General scheme of fragmentation of monofunctional organic compounds under electron ionization. Russ J Gen Chem 85, 556–566 (2015). https://doi.org/10.1134/S1070363215030056
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363215030056