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Chemistry of Heterocyclic Compounds

, Volume 15, Issue 4, pp 424–429 | Cite as

Mass-spectrometric behavior of polynuclear derivatives of benzo[f]quinoline

  • N. S. Kozlov
  • G. S. Shmanai
  • V. P. Suboch
  • V. I. Vil'chinskaya
Article
  • 28 Downloads

Abstract

It was established on the basis of a study of the mass spectra of benzo[f]quinoline derivatives that contain a methyl group or an aromatic or heterocyclic ring in the 1 position and various quinolyl groups (2-, 4-, and 6-quinolyl) in the 3 position that the geometry of the molecule has a decisive effect on the strength of the chemical bond between the substituents and the benzoquinoline ring. The degree of coplanarity of the heterocyclic rings determines the strength of interannular conjugation and consequently the strength of the bond between the rings. For the investigated polyheterocyclic systems the coplanarity increases in the order 2-quinolyl < 6-quinolyl < 4-quinolyl. This fact in turn has a strong effect on the pathway of mass-spectrometric fragmentation for each series of derivatives, and this makes it possible to reliably distinguish the 2-, 4-, and 6-quinolyl derivatives from their mass spectra.

Keywords

Methyl Mass Spectrum Organic Chemistry Chemical Bond Quinoline 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • N. S. Kozlov
    • 1
    • 2
  • G. S. Shmanai
    • 1
    • 2
  • V. P. Suboch
    • 1
    • 2
  • V. I. Vil'chinskaya
    • 1
    • 2
  1. 1.Institute of Physical Organic ChemistryAcademy of Sciences of the Belorussian SSRMinsk
  2. 2.Institute of PhysicsAcademy of Sciences of the Belorussian SSRMinsk

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