Skip to main content

Zusammenfassung

Alkane

Alkene

Alkine

Alicyclische Kohlenwasserstoffe

Aromatische Kohlenwasserstoffe

Heteroaromatische Verbindungen

Halogenverbindungen

Alkohole und Phenole

Hydroperoxide

Ether

Aliphatische Epoxide

Aliphatische Peroxide

Amine

Nitroverbindungen

Diazoverbindungen und Azobenzole

Azide

Nitrile und Isonitrile

Cyanate, Isocyanate, Thiocyanate und Isothiocyanate

Thiole

Sulfide und Disulfide

Sulfoxide und Sulfone

Sulfonsäuren, Sulfonsäureester und Sulfonamide

Thiocarbonsäure-S-ester

Aldehyde

Ketone

Carbonsäuren

Carbonsäureanhydride

Ester und Lactone

Amide und Lactame

Imide

Trialkylsilylether

Phosphorverbindungen

Massenspektren üblicher Lösungsmittel und Matrixkomponenten

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 44.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Literatur

  • [1] J.T. Bursey, M.M. Bursey, D.G. Kingston, Intramolecular hydrogen transfer in mass spectra. 1. Rearrangements in aliphatic hydrocarbons and aromatic compounds, Chem. Rev. 1973, 73, 191.

    Article  CAS  Google Scholar 

  • [2] K. Levsen, H. Heimbach, G.J. Shaw, G.W.A. Milne, Isomerization of hydrocarbon ions. VIII. The electron impact induced decomposition of n-dodecane, Org. Mass Spectrom. 1977, 12, 663.

    Article  CAS  Google Scholar 

  • [3] A. Lavanchy, R. Houriet, T. Gäumann, The mass spectrometric fragmentation of n-alkanes, Org. Mass Spectrom. 1979, 14, 79.

    Article  CAS  Google Scholar 

  • [4] W.M.A. Niessen, R.A. Correa C., Interpretation of MS-MS Mass Spectra of Drugs and Pesticides, Wiley, Hoboken, 2017.

    Google Scholar 

  • [5] A.G. Loudon, A. Maccoll, The mass spectrometry of the double bond. In: The Chemistry of Alkenes, Vol. 2; J. Zabicky, Ed.; Interscience: London, 1970; p. 327.

    Google Scholar 

  • [6] J.T. Bursey, M.M. Bursey, D.G. Kingston, Intramolecular hydrogen transfer in mass spectra. 1. Rearrangements in aliphatic hydrocarbons and aromatic compounds, Chem. Rev. 1973, 73, 191.

    Article  CAS  Google Scholar 

  • [7] N.J. Jensen, M.L. Gross, Localization of double bonds. Mass Spectrom. Rev. 1987, 6, 497.

    Google Scholar 

  • [8] C. Dass, Ion–molecule reactions of [ketene]+· as a diagnostic probe for distinguishing isomeric alkenes, alkynes, and dienes: A study of the C4H8 and C5H8 isomeric hydrocarbons, Org. Mass Spectrom. 1993, 28, 940.

    Article  CAS  Google Scholar 

  • [9] C. Lifshitz, A. Mandelbaum, Mass spectrometry of acetylenes. In: The Chemistry of the Carbon-Carbon Triple Bond, Part 1; S. Patai, Ed.; Wiley: Chichester, 1978; p. 157.

    Google Scholar 

  • [10] J.T. Bursey, M.M. Bursey, D.G. Kingston, Intramolecular hydrogen transfer in mass spectra. 1. Rearrangements in aliphatic hydrocarbons and aromatic compounds, Chem. Rev. 1973, 73, 191.

    Article  CAS  Google Scholar 

  • [11] H. Schwarz, The chemistry of ionized cyclopropanes in the gas phase. In: The Chemistry of the Cyclopropyl Group, Part 1; Z. Rappoport, Ed.; Wiley: Chichester, 1987; p. 173.

    Google Scholar 

  • [12] J.R. Collins, G.A. Gallup, Energy surfaces in the cyclopropane radical ion and the photoelectron spectrum of cyclopropane, J. Am. Chem. Soc. 1982, 104, 1530.

    Article  CAS  Google Scholar 

  • [13] G.D. Willet, T. Baer, Thermochemistry and dissociation dynamics of state-selected C4H4X ions. 3. C4H5N+, J. Am. Chem. Soc. 1980, 102, 6774.

    Google Scholar 

  • [14] E.F.H. Brittain, C.H.J. Wells, H.M. Paisley, Mass spectra of cyclobutanes and cyclohexanes of molecular formula C10H16, J. Chem. Soc. B 1968, 304.

    Google Scholar 

  • [15] J.T. Bursey, M.M. Bursey, D.G. Kingston, Intramolecular hydrogen transfer in mass spectra. 1. Rearrangements in aliphatic hydrocarbons and aromatic compounds, Chem. Rev. 1973, 73, 191.

    Article  CAS  Google Scholar 

  • [16] W. Schönfeld, Fragmentierungsdiagramme zur Aufklärung der Abbaureaktionen organischer Verbindungen I. Aromatische Kohlenwasserstoffe, Org. Mass Spectrom. 1975, 10, 321.

    Article  Google Scholar 

  • [17] C. Lifshitz, Tropylium ion formation from toluene: Solution of an old problem in organic mass spectrometry, Acc. Chem. Res. 1994, 27, 138.

    Google Scholar 

  • [18] M.V. Buchanan, B. Olerich, Differentiation of polycyclic aromatic hydrocarbons using electron-capture negative chemical ionization, Org. Mass Spectrom. 1984, 19, 486.

    Article  CAS  Google Scholar 

  • [19] W.M.A. Niessen, R.A. Correa C., Interpretation of MS-MS Mass Spectra of Drugs and Pesticides, Wiley, Hoboken, 2017.

    Google Scholar 

  • [20] Q.N. Porter, Mass Spectrometry of Heterocyclic Compounds, 2nd ed.; Wiley: New York, 1985.

    Google Scholar 

  • [21] D.G.I. Kingston, B.W. Hobrock, M.M. Bursey, J.T. Bursey, Intramolecular hydrogen transfer in mass spectra. III. Rearrangements involving the loss of small neutral molecules, Chem. Rev. 1975, 75, 693.

    Article  CAS  Google Scholar 

  • [22] R. Spilker, H.-F. Grützmacher, Isomerization and fragmentation of methylfuran ions and pyran ions in the gas phase, Org. Mass Spectrom. 1986, 21, 459.

    Article  CAS  Google Scholar 

  • [23] W. Riepe, M. Zander, Mass-spectrometric fragmentation behavior of thiophene benzologs, Org. Mass Spectrom. 1979, 14, 455.

    Google Scholar 

  • [24] H. Budzikiewicz, C. Djerassi, A.H. Jackson, G.W. Kenner, D.J. Newman, J.M. Wilson, Mass spectra of monocyclic derivatives of pyrrole, J. Chem. Soc. 1964, 1949.

    Google Scholar 

  • [25] W.M.A. Niessen, R.A. Correa C., Interpretation of MS-MS Mass Spectra of Drugs and Pesticides, Wiley, Hoboken, 2017.

    Google Scholar 

  • [26] A.G. Loudon, Mass spectrometry and the carbon-halogen bond. In: The Chemistry of the Carbon-Halogen Bond, Part 1; S. Patai, Ed.; Wiley: London, 1973; p. 223.

    Google Scholar 

  • [27] D.G.I. Kingston, B.W. Hobrock, M.M. Bursey, J.T. Bursey, Intramolecular hydrogen transfer in mass spectra. III. Rearrangements involving the loss of small neutral molecules, Chem. Rev. 1975, 75, 693.

    Article  CAS  Google Scholar 

  • [28] J.M. Miller, T.R.B. Jones, The mass spectra of azides and halides. In: Suppl. D: The Chemistry of Halides, Pseudo-Halides, and Azides, Part 1; S. Patai, Z. Rappoport, Eds.; Wiley: Chichester, 1983; p. 75.

    Google Scholar 

  • [29] W.M.A. Niessen, R.A. Correa C., Interpretation of MS-MS Mass Spectra of Drugs and Pesticides, Wiley, Hoboken, 2017.

    Google Scholar 

  • [30] K. Levsen, H.-M. Schiebel, J.K. Terlouw, K.J. Jobst, M. Elend, A. Preiss, H.Thiele, A Ingendoh, Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions, J. Mass Spectrom. 2007, 42, 1024.

    Article  CAS  PubMed  Google Scholar 

  • [31] D.G.I. Kingston, J.T. Bursey, M.M. Bursey, Intramolecular hydrogen transfer in mass spectra. II. The McLafferty rearrangement and related reactions, Chem. Rev. 1974, 74, 215.

    Article  CAS  Google Scholar 

  • [32] D.G.I. Kingston, B.W. Hobrock, M.M.Bursey, J.T. Bursey, Intramolecular hydrogen transfer in mass spectra. III. Rearrangements involving the loss of small neutral molecules, Chem. Rev. 1975, 75, 693.

    Article  CAS  Google Scholar 

  • [33] R.G. Cooks, The mass spectra of hydroxyl compounds. In: The Chemistry of the Hydroxyl Group, Part 2; S. Patai, Ed.; Interscience: London, 1971; p. 1045.

    Google Scholar 

  • [34] H. Schwarz, H.-M. Schiebel, Mass spectrometry of organic peroxides. In: The Chemistry of Peroxides; S. Patai, Ed.; Wiley: Chichester, 1983; p. 105.

    Google Scholar 

  • [35] C.C. van de Sande, The mass spectra of ethers and sulphides. In: The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogues, Suppl. E, Part 1; S. Patai, Ed.; Wiley: Chichester, 1980; p. 299.

    Google Scholar 

  • [36] S.L. Bernasek, R.G. Cooks, The β-cleavage reaction in ethers, Org. Mass Spectrom. 1970, 3, 127.

    Article  CAS  Google Scholar 

  • [37] J.P. Morizur, C. Djerassi, Mass spectrometric fragmentation of unsaturated ethers, Org. Mass Spectrom. 1971, 5, 895.

    Article  CAS  Google Scholar 

  • [38] G. Sozzi, H.E. Audier, P. Morgues, A. Millet, Alkyl phenyl ether radical cations in the gas phase: A reaction model, Org. Mass Spectrom. 1987, 22, 746.

    Article  CAS  Google Scholar 

  • [39] Q.N. Porter, Mass Spectrometry of Heterocyclic Compounds, 2nd ed.; Wiley: New York, 1985.

    Google Scholar 

  • [40] W.M.A. Niessen, R.A. Correa C., Interpretation of MS-MS Mass Spectra of Drugs and Pesticides, Wiley, Hoboken, 2017.

    Google Scholar 

  • [41] K. Levsen, H.-M. Schiebel, J.K. Terlouw, K.J. Jobst, M. Elend, A. Preiss, H.Thiele, A Ingendoh, Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions, J. Mass Spectrom. 2007, 42, 1024.

    Article  CAS  PubMed  Google Scholar 

  • [42] H. Schwarz, K. Levsen, The chemistry of ionized amino, nitroso and nitro compounds in the gas phase. In: Suppl. F, The Chemistry of the Amino, Nitroso and Nitro Compounds and Their Derivatives, Part 1; S. Patai, Ed.; Wiley: Chichester, 1982; p. 85.

    Google Scholar 

  • [43] D.G.I. Kingston, B.W. Hobrock, M.M. Bursey, J.T. Bursey, Intramolecular hydrogen transfer in mass spectra. III. Rearrangements involving the loss of small neutral molecules, Chem. Rev. 1975, 75, 693.

    Article  CAS  Google Scholar 

  • [44] R.D. Bowen, The chemistry of CnH2n+2N+ ions, Mass Spectrom. Rev. 1991, 10, 225.

    Article  CAS  Google Scholar 

  • [45] K.-P. Zeller, Mass spectra of cyano, isocyano and diazo compounds. In: Suppl. C, The Chemistry of Triple-Bonded Functional Groups, Part 1; S. Patai, Z. Rappoport, Eds.; Wiley: Chichester, 1983; p. 57.

    Google Scholar 

  • [46] C.W. Thomas, L.L. Levsen, Electron-impact spectra of 2-diazoacetophenones, Org. Mass Spectrom. 1978, 13, 39.

    Article  CAS  Google Scholar 

  • [47] J.M. Miller, T.R.B. Jones, The mass spectra of azides and halides. In: Suppl. D, The Chemistry of Halides, Pseudo-Halides and Azides, Part 1; S. Patai, Z. Rappoport, Eds.; Wiley: Chichester, 1983; p. 75.

    Google Scholar 

  • [48] R.A. Abramovitch, E.P. Kyba, E.F. Scriven, Mass spectrometry of aryl azides, J. Org. Chem. 1971, 36, 3796.

    Article  CAS  Google Scholar 

  • [49] K.A. Jensen, G. Schroll, Mass spectra of cyanates, isocyanates, and related compounds. In: The Chemistry of Cyanates and Their Thio Derivatives, Part 1; S. Patai, Ed.; Wiley: Chichester, 1977, p. 273.

    Google Scholar 

  • [50] W.M.A. Niessen, R.A. Correa C., Interpretation of MS-MS Mass Spectra of Drugs and Pesticides, Wiley, Hoboken, 2017.

    Google Scholar 

  • [51] M. Holcapek, R. Jirásko, M. Lisa, Basic rules for the interpretation of atmospheric pressure ionisation mass spectra of small molecules, J. Chromatogr. A, 2010, 1217, 3908.

    Article  PubMed  CAS  Google Scholar 

  • [11] K. Levsen, H.-M. Schiebel, J.K. Terlouw, K.J. Jobst, M. Elend, A. Preiss, H.Thiele, A Ingendoh, Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions, J. Mass Spectrom. 2007, 42, 1024.

    Article  CAS  PubMed  Google Scholar 

  • [52] C.C. van de Sande, The mass spectra of ethers and sulphides. In: Suppl. E, The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogues, Part 1; S. Patai, Ed.; Wiley: Chichester, 1980; p. 299.

    Google Scholar 

  • [53] C. Lifshitz, Z.V. Zaretskii, The mass spectra of thiols. In: The Chemistry of the Thiol Group, Part 1; S. Patai, Ed.; Wiley: London, 1974; p. 325.

    Google Scholar 

  • [54] Q.N. Porter, Mass Spectrometry of Heterocyclic Compounds, 2nd ed.; Wiley: New York, 1985.

    Google Scholar 

  • [55] K. Pihlaja, Mass spectra of sulfoxides and sulfones. In: The Chemistry of Sulphones and Sulphoxides; S. Patai, Z. Rappoport, C.G. Stirling, Eds.; Wiley: Chichester, 1988; p. 125.

    Google Scholar 

  • [56] R.A. Khmel’nitskii, Y.A. Efremov, Rearrangements in sulphoxides and sulphones induced by electron impact, Russ. Chem. Rev. 1977, 46, 46.

    Article  Google Scholar 

  • [57] S. Fornarini, Mass spectrometry of sulfonic acids and their derivatives; In: The Chemistry of Sulphonic Acids, Esters, and their Derivatives; S. Patai, Z. Rappoport, Eds.; Wiley: Chichester, 1991; p. 73.

    Google Scholar 

  • [58] K.B. Tomer, C. Djerassi, Mass spectrometry in structural and stereochemical problems—CCXXV: Sulfur migration in the [M–C2H4]+· ion of S-ethyl thiobenzoate, Org. Mass Spectrom. 1973, 7, 771.

    Article  CAS  Google Scholar 

  • [59] W.M.A. Niessen, R.A. Correa C., Interpretation of MS-MS Mass Spectra of Drugs and Pesticides, Wiley, Hoboken, 2017.

    Google Scholar 

  • [60] A. Weissberg, S. Dagan, Interpretation of ESI(+)-MS-MS spectra – Towards the identification of “unknowns”, Int. J. Mass Spectrom. 2011, 299, 158.

    Article  CAS  Google Scholar 

  • [61] M. Holcapek, R. Jirásko, M. Lisa, Basic rules for the interpretation of atmospheric pressure ionisation mass spectra of small molecules, J. Chromatogr. A, 2010, 1217, 3908.

    Article  PubMed  CAS  Google Scholar 

  • [62] K. Levsen, H.-M. Schiebel, J.K. Terlouw, K.J. Jobst, M. Elend, A. Preiss, H.Thiele, A Ingendoh, Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions, J. Mass Spectrom. 2007, 42, 1024.

    Article  CAS  PubMed  Google Scholar 

  • [63] P. Wright, A. Alex, D. Gibson, R.l Jones, P. Macrae, Characterisation of sulphoxides by atmospheric pressure ionisation mass spectrometry, Rapid Commun. Mass Spectrom. 2005, 19, 2005.

    Article  PubMed  CAS  Google Scholar 

  • [64] J.H. Bowie, Mass spectrometry of carbonyl compounds. In: The Chemistry of the Carbonyl Group, Vol. 2; J. Zabicky, Ed.; Interscience: London, 1970; p. 277.

    Google Scholar 

  • [65] S.W. Tam, Mass spectra of acid derivatives. In: Suppl. B, The Chemistry of Acid Derivatives, Part 1; S. Patai, Ed.; Wiley: Chichester, 1979; p. 121.

    Google Scholar 

  • [66] D.G.I. Kingston, J.T. Bursey, M.M. Bursey, Intramolecular hydrogen transfer in mass spectra. II. The McLafferty rearrangement and related reactions, Chem. Rev. 1974, 74, 215.

    Article  CAS  Google Scholar 

  • [67] D.G.I. Kingston, B.W. Hobrock, M.M.Bursey, J.T. Bursey, Intramolecular hydrogen transfer in mass spectra. III. Rearrangements involving the loss of small neutral molecules, Chem. Rev. 1975, 75, 693.

    Article  CAS  Google Scholar 

  • [68] A.G. Harrison, High-resolution mass spectra of aliphatic aldehydes, Org. Mass Spectrom. 1970, 3, 549.

    Article  CAS  Google Scholar 

  • [69] W.M.A. Niessen, R.A. Correa C., Interpretation of MS-MS Mass Spectra of Drugs and Pesticides, Wiley, Hoboken, 2017.

    Google Scholar 

  • [70] K. Levsen, H.-M. Schiebel, J.K. Terlouw, K.J. Jobst, M. Elend, A. Preiss, H.Thiele, A Ingendoh, Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions, J. Mass Spectrom. 2007, 42, 1024.

    Article  CAS  PubMed  Google Scholar 

  • [71] D.G.I. Kingston, B.W. Hobrock, M.M. Bursey, J.T. Bursey, Intramolecular hydrogen transfer in mass spectra. III. Rearrangements involving the loss of small neutral molecules, Chem. Rev. 1975, 75, 693.

    Article  CAS  Google Scholar 

  • [72] H. Schwarz, Positive and negative ion chemistry of silicon-containing molecules in the gas phase. In: The Chemistry of Organic Silicon Compounds, Part 1; S. Patai, Z. Rappoport, Eds.; Wiley: Chichester, 1989; p. 445.

    Google Scholar 

  • [73] D.G.I. Kingston, J.T. Bursey, M.M. Bursey, Intramolecular hydrogen transfer in mass spectra. II. The McLafferty rearrangement and related reactions, Chem. Rev. 1974, 74, 215.

    Article  CAS  Google Scholar 

  • [74] R. Orlando, Analysis of peptides contaminated with alkali-metal salts by fast atom bombardment mass spectrometry using crown ethers, Anal. Chem. 1992, 64, 332.

    Article  CAS  Google Scholar 

  • [75] P.K. Singh, L. Field, B.J. Sweetman, Organic disulfides and related substances, J. Org. Chem. 1988, 53, 2608.

    Article  CAS  Google Scholar 

  • [76] Z.-H. Huang, B.-J. Shyong, D.A. Gage, K.R. Noon, J. Allison, N-Alkylnicotinium halides: A class of cationic matrix additives for enhancing the sensitivity in negative ion fast-atom bombardment mass spectrometry of polyanionic analytes, J. Am. Soc. Mass Spectrom. 1994, 5, 935.

    Article  PubMed  CAS  Google Scholar 

  • [77] A.E. Ashcroft, Ionization Methods in Organic Mass Spectrometry, The Royal Society of Chemistry: Cambridge, 1997.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ernö Pretsch .

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer-Verlag GmbH Deutschland, ein Teil von Springer Nature

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Pretsch, E., Bühlmann, P., Badertscher, M. (2020). Massenspektrometrie. In: Spektroskopische Daten zur Strukturaufklärung organischer Verbindungen. Springer Spektrum, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-60950-7_8

Download citation

Publish with us

Policies and ethics