Chemistry of Heterocyclic Compounds

, Volume 20, Issue 6, pp 637–642 | Cite as

Mass spectrometry of 8-hydroxyquinoline derivatives

  • A. I. Ermakov
  • V. G. Voronin
  • A. A. Sorokin
  • N. I. Épshtein
  • I. D. Muravskaya
  • V. V. Chistyakov
  • A. P. Zuev
Article
  • 83 Downloads

Abstract

In contrast to the fragmentation of the corresponding alkyl aryl ethers, characteristic [M-H]+ and [M-H, -CO]+ fragments were observed in the fragmentation of 5-nitro(halo)-substituted 8-alkoxyquinolines. It was found by means of deuterium labeling that a hydrogen atom is split out primarily from the alkoxy group. It was demonstrated that an [M-H, -CO]+ fragment was formed from the [M-H]+ ion, which has a three-ring structure and a quaternary nitrogen atom. The formation of an [M-CO]+ fragment is characteristic for the fragmentation of 5(7)-nitro(halo)-substituted 8-hydroxyquinolines. The interrelationship between the intensities of the [M-H]+, [M-H, -CO]+, and [M-CO]+ ion peaks and the protonation constants (pKa) of the investigated compounds is discussed.

Keywords

Hydrogen Nitrogen Ether Mass Spectrometry Organic Chemistry 

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Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • A. I. Ermakov
    • 1
  • V. G. Voronin
    • 1
  • A. A. Sorokin
    • 1
  • N. I. Épshtein
    • 1
  • I. D. Muravskaya
    • 1
  • V. V. Chistyakov
    • 1
  • A. P. Zuev
    • 1
  1. 1.Branch of the S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical ChemistryKupavna

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