Journal of the Serbian Chemical Society p. 993 - 1001 (2012)
Update date:2022-08-28
Topics:
Drmanic, Sasa Z.
Marinkovic, Aleksandar D.
Nikolic, Jasmina B.
Jovanovic, Bratislav Z.
Hammett correlations between the 13C-NMR chemical shifts of the azomethine carbon atom and the corresponding substituent constants were established for thirteen Schiff bases. The successful correlation of the chemical shifts with the electrophilic substituent constants σ+ indicate a significant resonance interaction of the substituents on the aniline ring with the azomethine carbon atom in the examined series of imines. The demand for electrons in the investigated compounds was compared to that of the N-benzylideneanilines and N-(substituted phenyl)pyridinealdimines. The manner of transmission of the substituent effects is discussed and they were separated into resonance and inductive effects. The inductive effects prevail over the resonance effects.
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