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Molecular dynamics of (E)-6-acetyl-3-(2-hydroxy-5-methylphenyl)-5-styryl cyclohex-2-en-1-one and (E)-6-ethylcarboxylate-3-(2-hydroxy-5-methylphenyl)-5-styryl cyclohex-2-en-1-one in a solution studied by NMR spectroscopy


Correspondence to: I. G. Mamedov, Baku State University, Chemical Faculty, NMR Laboratory, Z. Khalilov 23, Baku, Azerbaijan. E-mail:


Molecular dynamics of cyclohexenone derivatives of (2E,4E)-1-(2-hydroxy-5-methylphenyl)-5-phenyl-2,4-pentadiene-1-one (chalcone) has been investigated in solutions using NMR. The results confirm the formation of O-H⋯O intramolecular hydrogen bond and the presence of keto–enol tautomeric transitions in the (E)-6-acetyl-3-(2-hydroxy-5-methylphenyl)-5-styryl cyclohex-2-en-1-one. The free energy of activation for the keto–enol tautomeric transitions has been calculated. The keto–enol tautomerism in the investigated compound has been also confirmed by chemical method. Copyright © 2013 John Wiley & Sons, Ltd.