Hydrogen bonding interaction between ethyl methacrylate and alcohols in non-polar solvents: An FTIR study

The association between ethyl methacrylate and n-butanol, s-butanol and t-butanol in non-polar solvents viz. n-heptane, CCl4, and benzene has been investigated by means of FTIR spectroscopy. The most likely association complex between alcohol and acrylic ester is 1: 1 stoichiometric complex through the free hydroxyl group of alcohol and the carbonyl group of ester. The formation constant of the 1: 1 complexes has been calculated using the Nash method. It is shown that the strength of the hydrogen bond (C=O:HO) in the various systems studied depends on the acidity of the R-OH proton and the steric factor of the alkyl group of the alkyl alcohol and also on the solvents used. The solvent effect on the formation of hydrogen bond equilibria is discussed in terms of specific interaction between the solute and solvent.