Mass-spectrometric behavior of polynuclear derivatives of benzo[f]quinoline
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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.
KeywordsMethyl Mass Spectrum Organic Chemistry Chemical Bond Quinoline
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