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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
Author(s) -
Mamedov I. G.,
Bayramov M. R.,
Mamedova Y. V.,
Maharramov A. M.
Publication year - 2013
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.3982
Subject(s) - tautomer , chemistry , enol , intramolecular force , cyclohexenone , chalcone , stereochemistry , hydrogen bond , medicinal chemistry , keto–enol tautomerism , proton nmr , computational chemistry , molecule , organic chemistry , catalysis
Molecular dynamics of cyclohexenone derivatives of (2 E ,4 E )‐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.