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1794127 
Journal Article 
Spectroscopic Studies and Keto-Enol Tautomeric Effect of Newer Schiff Bases of ortho-Hydroxy-benzaldehyde/naphthaldehyde with 1,2-Phenyienediamine and 4-Aminophenyl Ether 
Shah, A; Shah, AA 
2013 
Yes 
Asian Journal of Chemistry
ISSN: 0970-7077
EISSN: 0975-427X 
Chemical Publishing Co. 
25 
8 
4215-4218 
English 
WOS:000317246400020 
Hydroxyl Schiff bases derived from 1,2-phenylenediamine and 4-aminophenyl ether with o-hydroxy benzaldehyde or o-hydroxyl naphthaldehyde were used to investigate enol-imine and keto-amine tautomeric analysis. UV-visible spectra of the compounds have been investigated tautomeric equilibrium (enol-imine O-H···N, keto- amine O···H-N forms) in different polar and non-polar solvents systems. From FTIR spectra of these model compounds, were possible to assign the IR absorption for the C=O and C=N groups in both ketoamine and enol imine forms, respectively. The keto-enol forms was observed in basic solution of polar and nonpolar solvents such as ethanol, chloroform, DMF, benzene, cyclohexane, n-hexane and in acidic solutions of CHCl3, benzene and n-hexane not in ethanol and DMF. FTIR results were showed that all Schiff bases studied, favoured the enol-imine form over the keto form in a weakly polar solvent. 
Schiff base; Tautomerism; Keto-enamine; Enol-imine; Solvent effect