IR, Raman, SERS and DFT study of paroxetine

Structural investigations by different vibrational spectroscopic methods (FTIR, Raman and SERS), as well as density functional theory (DFT) calculations were performed on paroxetine (IUPAC name: (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine. After the identification of the lowest energy conformer of the investigated molecule, the FTIR, FT-Raman and SERS spectra were assigned on the basis of DFT calculations at B3LYP/6-31G(d) level of theory. The very good correlation found between experimental and theoretical data is a clear evidence for a reliable assignment of the vibrational bands. The molecular electrostatic potential was calculated and used for the prediction of preferred adsorption sites of the paroxetine molecule on the silver nanoparticles surface. Based on SERS spectra analysis it is shown that the molecule is adsorbed on the silver surface through the benzodioxol ring, in a tilted orientation.