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Massenspektrometrie

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Book cover Spektroskopische Daten zur Strukturaufklärung organischer Verbindungen

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Zusammenfassung

Fragmentierung: Größere Alkylfragmente (Cn>4) werden im wesentlichen durch direkte Fragmentierung gebildet. Die Fragmente können dehydrieren und zeigen umfangreiche Umlagerungen von H-Atomen und des Gerüsts. Dabei können sich Atomgruppen aus dem Inneren der Fragmente abspalten, und die Enden können rekombinieren. Kleinere Alkylfragmente (C2 bis C4) werden meist durch Zerfall höherer Fragmente gebildet.

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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—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. A.G. Loudon, A. Maccoll, The mass spectrometry of the double bond. In: The Chemistry of Alkenes, Vol. 2; J. Zabicky, Hrsg.; Interscience: London, 1970; S. 327.

    Google Scholar 

  5. 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 

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

    Article  CAS  Google Scholar 

  7. 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 

  8. C. Lifshitz, A. Mandelbaum, Mass spectrometry of acetylenes. In: The Chemistry of the Carbon-Carbon Triple Bond; S. Patai, Hrsg.; Wiley: Chichester, 1978; S. 157.

    Chapter  Google Scholar 

  9. 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 

  10. H. Schwarz, The chemistry of ionized cyclopropanes in the gas phase. In: The Chemistry of the Cyclopropyl Group, Part 1; Z. Rappoport, Hrsg.; Wiley: Chichester, 1987; S. 173.

    Google Scholar 

  11. J.R. Collins, G.A. Gallup, Energy surfaces in the cyclopropane radical ion and the photo-electron spectrum of cyclopropane, J. Am. Chem. Soc. 1982, 104, 1530.

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  13. 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 

  14. 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 

  15. W. Schönfeld, Fragmentierungsdiagramme zur Aufklärung der Abbaureaktionen organischer Verbindungen. 1. Aromatische Kohlenwasserstoffe, Org. Mass. Spectrom. 1975, 10, 321.

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  17. 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 

  18. Q.N. Porter, Mass Spectrometry of Heterocyclic Compounds, 2. Aufl.; Wiley: New York, 1985.

    Google Scholar 

  19. 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 

  20. 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 

  21. W. Riepe, M. Zander, Mass-spectrometric fragmentation behavior of thiophene benzologs. Org. Mass. Spectrom. 1979, 14, 455.

    Article  CAS  Google Scholar 

  22. H. Budzikiewicz, D. Djerassi, A.H. Jackson, G.W. Kenner, D. J. Newmann, J. M. Wilson, Mass spectra of monocyclic derivatives of pyrrole, J. Chem. Soc. 1964, 1949.

    Google Scholar 

  23. A.G. Loudon, Mass spectrometry and the carbon-halogen bond. In: The Chemistry of the Carbon-Halogen Bond, Part 1; S. Patai, Hrsg.; Wiley: London, 1973; S. 223.

    Chapter  Google Scholar 

  24. 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 

  25. 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, Hrsg.; Wiley: Chichester, 1983; S. 75.

    Chapter  Google Scholar 

  26. 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 

  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. R.G. Cooks, The mass spectra of hydroxyl compounds. In: The Chemistry of the Hydroxyl Group, Part 2; S. Patai, Hrsg.; Interscience: London, 1971; S. 1045.

    Chapter  Google Scholar 

  29. H. Schwarz, H.-M. Schiebel, Mass spectrometry of organic peroxides. In: The Chemistry of Peroxides; S. Patai, Hrsg.; Wiley: Chichester 1983; S. 105.

    Google Scholar 

  30. 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, Hrsg.; Wiley: Chichester, 1980; S. 299.

    Google Scholar 

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

    Article  CAS  Google Scholar 

  32. J.P. Morizur, C. Djerassi, Mass spectrometric fragmentation of unsaturated ethers, Org. Mass Spectrom. 1971, 5, 895.

    Article  CAS  Google Scholar 

  33. 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 

  34. Q.N. Porter, Mass Spectrometry of Heterocyclic Compounds, 2. Aufl.; Wiley: New York, 1985.

    Google Scholar 

  35. 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, Hrsg.; Wiley: Chichester, 1982; S. 85.

    Chapter  Google Scholar 

  36. 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 

  37. R.D. Bowen, The chemistry of CnH2n+2N+ ions. Mass Spectrom. Rev. 1991, 10, 225.

    Article  CAS  Google Scholar 

  38. 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, Hrsg.; Wiley: New York, 1983; S. 57.

    Chapter  Google Scholar 

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

    Article  CAS  Google Scholar 

  40. 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, Hrsg.; Wiley: Chichester, 1983; S. 75.

    Chapter  Google Scholar 

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

    Article  CAS  Google Scholar 

  42. 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, Hrsg.; Wiley: Chichester, 1977; S. 273.

    Chapter  Google Scholar 

  43. 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, Hrsg.; Wiley: Chichester, 1980; S. 299.

    Google Scholar 

  44. C. Lifshitz, Z.E. Zaretskii, The mass spectra of thiols. In: The Chemistry of the Thiol Group, Part 1; S. Patai, Hrsg.; Wiley: London, 1974; S. 325.

    Google Scholar 

  45. Q.N. Porter, Mass Spectrometry of Heterocyclic Compounds, 2. Aufl.; Wiley: New York, 1985.

    Google Scholar 

  46. K. Pihlaja, Mass spectra of sulfoxides and sulfones. In: The Chemistry of Sulphones and Sulphoxides; S. Patai, Z. Rappoport, Ch. Stirling, Hrsg.; Wiley: Chichester, 1988; S. 125.

    Chapter  Google Scholar 

  47. 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 

  48. S. Fornarini, Mass spectrometry of sulfonic acids and their derivatives. In: The Chemistry of Sulphonic Acids, Esters and their Derivatives; S. Patai, Z. Rappoport, Hrsg.; Wiley: Chichester, 1991.

    Google Scholar 

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

    Article  CAS  Google Scholar 

  50. J.H. Bowie, Mass spectrometry of carbonyl compounds. In: The Chemistry of the Carbonyl Group, Bd. 2; J. Zabicky, Hrsg.; Interscience: London, 1970; S. 277.

    Google Scholar 

  51. S.W. Tarn, Mass spectra of acid derivatives. In: The Chemistry of Aid Derivatives, Part 1; S. Patai, Hrsg.; Wiley: Chichester, 1979.

    Google Scholar 

  52. 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 

  53. 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 

  54. A.G. Harrison, High-resolution mass spectra of aliphatic aldehydes, Org. Mass Spectrom. 1970, 3, 549.

    Article  CAS  Google Scholar 

  55. 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 

  56. H. Schwarz, Positive and negative ion chemistry of silicon-containing molecules in the gas phase. In: The Chemistry of Organic Silicon Compounds; S. Patai, Z. Rappoport, Hrsg.; Wiley: Chichester, 1989; S. 445.

    Chapter  Google Scholar 

  57. 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 

  58. 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 

  59. P.K. Singh, L. Field, B.J. Sweetman, Organic disulfides and related substances. 49. Preparation of Cyclic thiosulfates and reactions with thiols, J. Org. Chem. 1988, 53, 2608.

    Article  CAS  Google Scholar 

  60. 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, 928.

    Article  Google Scholar 

  61. A.E. Ashcroft, Ionization in Organic Mass Spectrometry, RSC Analytical Spectroscopy Monographs, The Royal Society of Chemistry: Cambridge, 1997.

    Google Scholar 

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Authors and Affiliations

  1. Laboratorium für Organische Chemie, ETH Zürich, CH-8092, Zürich, Schweiz

    Professor Ernö Pretsch & Dr. Martin Badertscher

  2. Department of Chemistry, University of Minnesota, 207 Pleasant St., SE, Minneapolis, MN, 55455, USA

    Professor Philippe Bühlmann

  3. Aengerich 8, CH-3303, Muenchringen, Schweiz

    Dr. Christian Affolter

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  2. Professor Philippe Bühlmann
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  4. Dr. Martin Badertscher
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© 2001 Springer-Verlag Berlin Heidelberg

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Pretsch, E., Bühlmann, P., Affolter, C., Badertscher, M. (2001). Massenspektrometrie. In: Spektroskopische Daten zur Strukturaufklärung organischer Verbindungen. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-09972-8_7

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  • DOI: https://doi.org/10.1007/978-3-662-09972-8_7

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-41877-1

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