Synthesis and spectroscopic studies of schiff bases from Variously substituted benzaldhydes and 2-aminomethyl pyridine

Abstract

Variously substituted hydroxybenzaldimines have been synthesized from the condensation of salicylaldehyde, o-vanillin, p-vanillin or vanillin with 2-aminomethyl pyridine. The compounds were characterized using elemental analyses, FT-IR, UV-vis. The spectroscopic methods showed the Schiff bases exist as a mixture of tautomer. The electronic effects of the variously substituted hydroxybenzaldehydes were examined in methanol and dimethylformamide (DMF). It was observed that the electronic effects of the substituents and solvents influenced the intramolecular hydrogen bonding via the conjugation of the heterocyclic ring or by modifying the capacity of the nitrogen atom from entering into hydrogen bonding.

 Keywords: Substituted Hydroxybenzaldimines, Tautomerism