FTIR study of hydrogen bonding between substituted benzyl alcohols and acrylic esters

Hydrogen bonding between substituted benzyl alcohols (benzyl alcohol, o-aminobenzyl alcohol, o-chlorobenzyl alcohol and o-nitrobenzyl alcohol) and acrylic esters (methyl methacrylate, ethyl methacrylate) is studied in carbon tetrachloride by using the FTIR spectroscopic method. Utilizing the Nash method, the formation constant (K) of the 1: 1 complexes is calculated. Using the K value, the Gibbs free energy change (Delta G(0)) is also calculated. The calculated formation constant and Gibbs free energy change values vary with the substituent of benzyl alcohol and ester chain length, which suggests that the proton donating ability of substituted benzyl alcohols is in the order: o-aminobenzyl alcohol < benzyl alcohol < o-chlorobenzyl alcohol < o-nitrobenzyl alcohol, and proton accepting ability of acrylic esters is in the order: methyl methacrylate < ethyl methacrylate. (C) 2012 Production and hosting by Elsevier B.V. on behalf of King Saud University.