Abstract
The molecular structure and spectroscopic properties of 9-fluorenone hydrazone have been studied experimentally and theoretically. H-1, C-13 and DEPT-135 NMR spectra of 9-fluorenone hydrazone are reported in four different solvents: CD3CN, CDCl3, DMSO-d(6) and methanol-d(4). The crystal and molecular structure has been determined by single crystal X-ray. It shows that the molecule is crystalline as a monoclinic with space group of P2(1). Other structural and electronic properties have been determined using ESI+-MS, FT-ER and UV-Vis techniques. Theoretical calculations have been performed to obtain the main structural and electronic properties of the compound, and compared with experimental values. The computational study has been carried out using density functional theory (DFT) method at B3LYP/6-311-HFG(d,p) level of theory. The theoretical vibrational frequencies obtained by DFT calculations are in good agreement with the experimental values. Time dependent-DFT (TD-DFT) calculations have been carried out in both gas phase and in different solvent systems using polarizable continuum model (PCM) to calculate the electronic absorption spectra. GIAO method has been used to calculate the NMR spectra in different solvents. The correlation coefficients between the calculated and experimental chemical shifts are mostly in the range of 0.91-0.98 for H-1 NMR, whereas the correlation coefficients for C-13 NMR in all solvents are equal to 0.99.