High resolution mass spectrometry. Part X. Loss of water from the molecular ions of aromatic amides

Lord, G. H.; Millard, B. J.; Memel, Joachim

doi:10.1039/p19730000572

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J. Chem. Soc., Perkin Trans. 1

1973

DOI: 10.1039/p19730000572

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High resolution mass spectrometry. Part X. Loss of water from the molecular ions of aromatic amides

G. H. Lord¹,

B. J. Millard²,

Joachim Memel³

Abstract: Thermal loss of water by aromatic amides in the mass spectrometer is well known ; it is now shown that when the amide group i s flanked by both a methyl and a nitro-group elimination of water occurs by an electron-impact process. In view of the results of deuterium-labelling studies a mechanism is proposed for this loss in the case of 1 -methyl-4-nitroimidazole-5-carboxamide. It is further shown that the resulting ion does not have the nitrile structure.

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Cited by 8 publications

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ChemInform Abstract: MASSENSPEKTROMETRIE MIT HOHER AUFLOESUNG 10. MITT. VERLUST VON WASSER AUS DEN MOLEKUELIONEN AROMATISCHER AMIDE

Lord¹,

Millard²,

Memel³

1973

Chemischer Informationsdienst

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ChemInform Abstract: MASSENSPEKTROMETRIE MIT HOHER AUFLOESUNG 10. MITT. VERLUST VON WASSER AUS DEN MOLEKUELIONEN AROMATISCHER AMIDE

Lord¹,

Millard²,

Memel³

1973

Chemischer Informationsdienst

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Fragmentation reactions of singly and doubly protonated thiourea‐ and sugar‐substituted cyclams and their transition‐metal complexes

et al. 2008

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Cyclam macrocycles tetrasubstituted with amino-, thiourea-, and sugar-terminated side chains are ionized by electrospray ionization mass spectrometry (ESI-MS) as singly or doubly protonated species or as transition-metal complexes. Their fragmentation behavior is examined in a Fourier-transform ion-cyclotron-resonance (FT-ICR) mass spectrometer by collision-induced dissociation (CID) experiments. Typically, fragmentation occurs within the side chains through a number of different 1,2-elimination reactions irrespective of the absence or presence of a transition metal ion such as Co(2+), Ni(2+), or Zn(2+). A remarkable exception is Cu(2+), which induces ring cleavage reactions. This is traced back to an electron transfer from the cyclam nitrogen atoms to the Cu(2+) ion. The electron transfer creates a cation-radical within the macrocycle, which induces typical fragmentation reactions such as alpha-cleavages that lead to fragmentation within the macrocycle. This interpretation is in line with fragmentation experiments on unsubstituted cyclam and its complexes.

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Nachbargruppeneffekte bei der Elektronenstoß‐Induzierten Fragmentierung von Acetylierten 2.2′‐Diamino‐Diphenylmethanen

Eckhardt

Fehlhaber

Volk

et al. 1974

Org. Mass Spectrom.

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The mono-and bis-acetylated 2,2'-diamino-diphenylmethanes (I to V) exhibit strong elimination of water from the molecular ions upon electron-impact. The corresponding fragmentation processes were investigated by means of deuterium labelling.Zusammenfassung-Die mono-und bis-acetylierten 2.2'-Diamino-diphenylmethane (I bis V) spalten beim ElektronenstoO-induzierten Zerfall in starkem MaDe aus den Molekiilionen Wasser ab. Die zugrundeliegenden Fragmentierungsprozesse wurden mit Hilfe deuterierter Verbindungen untersucht.

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High resolution mass spectrometry. Part X. Loss of water from the molecular ions of aromatic amides

Cited by 8 publications

References 0 publications

ChemInform Abstract: MASSENSPEKTROMETRIE MIT HOHER AUFLOESUNG 10. MITT. VERLUST VON WASSER AUS DEN MOLEKUELIONEN AROMATISCHER AMIDE

ChemInform Abstract: MASSENSPEKTROMETRIE MIT HOHER AUFLOESUNG 10. MITT. VERLUST VON WASSER AUS DEN MOLEKUELIONEN AROMATISCHER AMIDE

Fragmentation reactions of singly and doubly protonated thiourea‐ and sugar‐substituted cyclams and their transition‐metal complexes

Nachbargruppeneffekte bei der Elektronenstoß‐Induzierten Fragmentierung von Acetylierten 2.2′‐Diamino‐Diphenylmethanen

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