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Hydrogen bonding involving α,β-unsaturated carboxylic esters and substituted phenols: an infrared spectroscopic study

Authors
Journal
Journal of Molecular Structure
0022-2860
Publisher
Elsevier
Publication Date
Volume
263
Identifiers
DOI: 10.1016/0022-2860(91)80058-c
Disciplines
  • Physics

Abstract

Abstract The hydrogen-bonded complexes between phenol derivatives and methyl acrylate, methyl trans- crotonate and methyl trans-cinnamate were studied in carbon tetrachloride solution by infrared spectroscopy. Temperature variation studies were used to evaluate both formation constants and the enthalpies of complex formation. It is shown that the relative values of enthalpies associated with the hydrogen bonding process in the various systems studied depend on the substituent constants of both the ester and phenol substituents. In addition, it is also shown that the observed shifts in the carbonyl stretching frequency upon complexation can be correlated with Δ H, thus providing a useful indirect way of measuring the strength of the hydrogen bond.

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