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THE EFFECT OF ACIDS ON THE INFRARED SPECTRA OF SCHIFF BASES—II. IMINES CONTAINING THE C=C‐C=N AND C=C‐C=C‐C=N UNITS

Abstract— The Fourier‐transform infrared spectra of chloroform‐d solutions of conjugated imines CH3CH=CHCH=NCH(CH3)2 and CH3CH2CH=CHCH=CHCH=NCH(CH3)2 and the related protonated species with HCl, HBr, HI, trichloro, dichloro, monobromo and monochloroacetic acids or propionic acid are presented. The effects of conjugation and protonation are examined. The results show that conjugation slightly increases the basicity of the Schiff bases. HCl, HBr and HI protonate the Schiff bases completely. The carboxylic acids protonate partially depending on their pKa, values. When the Schiff base contains two (or more) C=C bonds conjugated with C=N, the main C=C stretching band undergoes a strong intensification showing that sizeable dipole moment variations occur along the conjugated chain.