Infrared studies on hydrogen bonding interaction between acrylic esters with 1-dodeconal and phenol in carbon tetrachloride

The influence of the hydroxyl group in 1-dodeconal and phenol on the carbonyl vibration of representative compounds belonging to methyl methacrylate, ethyl methacrylate and butyl methacrylate in carbon tetrachloride has been studied by Fourier transform infrared spectroscopic method. The integrated intensities and change in dipole moments for O-H and C=O bonds were calculated. The formation constants of the 1 : 1 complexes have been calculated using Nash's method. The values of the formation constant and Gibbs energy vary with the ester chain length, which suggests that the strengths of the intermolecular hydrogen bonds (O-H center dot center dot center dot O=C) are dependent on the alkyl group of the acrylic ester and the results show that the proton accepting ability of acrylic esters is in the order methyl methacrylate < ethyl methacrylate < butyl methacrylate. The strength of the intermolecular C=O: HO bonds is also shown to be dependent on the basicity of the C=O group of acrylic esters and the acidity of the proton donor.