A spectrophotometric study of impact of solvent, substituent and cross-conjugation in some 4-aminoantipyrine based Schiff bases

Abstract The influences of substituent and solvent polarity on the electronic transition of seven different 4-aminoantipyrine based Schiff bases have been investigated in 14 solvents of different polarity. Reichardt'sET(30) scale has been used to propose a quantitative approach towards the relative stability of the electronic ground and excited state species. The Schiff bases can sense the polarity changes of the solvents and accordingly there appear three categories of solvents: non-polar, dipolar aprotic and polar protic. The first two categories of solvents induce negative solvatochromism and the third one induces positive solvatochromism in the molecules. Cross conjugation and geometrical configuration have been proposed to play an important role in the extent of electronic transition of the Schiff bases in various solvent media. Out of various substituent effects, field effect and resonance significantly influence the electronic environment of the compounds, as evidenced from the regression models involving change in UV–Vis absorption wavelengths 1HNMR chemical shifts and IR frequencies.