NBO, conformational, NLO, HOMO–LUMO, NMR and electronic spectral study on 1-phenyl-1-propanol by quantum computational methods

•The compound 1-phenyl-1-propanol investigated by FT-IR, FT-Raman and NMR and UV–Vis spectroscopic tool.•The chemical shift is found in favor of its change of chemical property.•The charge transfer in the molecule by HOMO–LUMO studied in relation with NBO analysis.•The study of NLO property in relation with polarizability and hyperpolarizability is done.•Chemical reactivity region have been found along with the Fukui function.

In this study, FT-IR, FT-Raman, NMR and UV spectra of 1-phenyl-1-propanol, an intermediate of anti-depressant drug fluoxetine, has been investigated. The theoretical vibrational frequencies and optimized geometric parameters have been calculated by using HF and density functional theory with the hybrid methods B3LYP, B3PW91 and 6-311+G(d,p)/6-311++G(d,p) basis sets. The theoretical vibrational frequencies have been found in good agreement with the corresponding experimental data. 1H and 13C NMR spectra were recorded and chemical shifts of the molecule were compared to TMS by using the Gauge-Independent Atomic Orbital (GIAO) method. A study on the electronic and optical properties, absorption wavelengths, excitation energy, dipole moment and frontier molecular orbital energies are performed using HF and DFT methods. The thermodynamic properties (heat capacity, entropy and enthalpy) at different temperatures are also calculated. NBO analysis is carried out to picture the charge transfer between the localized bonds and lone pairs. The local reactivity of the molecule has been studied using the Fukui function. NLO properties related to polarizability and hyperpolarizability are also discussed.

Graphical abstract1-Phneyl-1-propanol is used as intermediate for composition of fluoxetine anti-depressant drug. It is a major depression drug for pediatric depression. Though the molecule has symmetry, it has different trans–cis structure with tiny different energies. The theoretical vibrational frequencies have been found in good agreement with the corresponding experimental data. 1H and 13C NMR spectra were recorded and chemical shifts of the molecule were compared to TMS by using the Gauge-Independent Atomic Orbital (GIAO) method. A study on the electronic and optical properties, absorption wavelengths, excitation energy, dipole moment and frontier molecular orbital energies are performed using HF and DFT methods.Figure optionsDownload full-size imageDownload as PowerPoint slide