Characterization of H-bonding networks in chiral alcohols using Infrared, Raman and Vibrational Circular Dichroism spectroscopies, and density functional calculations: (S)-(−)-perillyl alcohol

For the first time, a study of the H-bonding network in which the chiral alcohol (4-isopropenylcyclohex-1-en-1-yl)methanol [(S)-(−)-perillyl alcohol] is involved (in neat liquid and in CCl4 solution) is carried out. For this task, Infrared (IR), Raman and Vibrational Circular Dichroism (VCD) spectroscopies are applied together with theoretical calculations based on Density Functional Theory. Most of the experimental features are reproduced taking into account five different rotamers of the monomer, a dimer, and a cyclic trimer. For this species, IR and Raman techniques are useful to study H-bonding networks only in the 4000–3200 cm−1 region. In contrast, VCD spectroscopy is useful in the 4000–900 cm−1 region.

Monomer, dimer, and trimer structures of S-(−)-perillyl alcohol and detail of the IR-VCD spectra.Figure optionsDownload as PowerPoint slide