Molecular structure, vibrational and electronic properties of 4-Phenyl-3H-1,3-thiazol-2-ol using density functional theory and comparison of drug efficacy of keto and enol forms by QSAR analysis

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2014-11, Vol.132, p.568-581
• Main Authors: Sachan, Alok K., Pathak, Shilendra K., Chand, Satish, Srivastava, Ruchi, Prasad, Onkar, Belaidi, Salah, Sinha, Leena
• Format: Article
• Language: English
• Subjects: FT-IR; FT-Raman and UV–Vis spectra; NBO analysis; QSAR; Vibrational analysis
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2014.05.011

[Display omitted] •FT-Raman, FT-IR and UV-Vis analysis of 4-Phenyl-3H-1,3-thiazol-2-ol has been done.•DOS and PDOS plots drawn to show the make–up of the molecular orbitals.•QSAR analysis of both the keto and enol form establishes the efficacy of enol form. 4-Phenyl-3H-1,3-thiazol-2-ol can exist in two tautomeric forms – keto and enol. Comprehensive investigation of molecular geometry and electronic structure in ground as well as in the first excited state of 4-Phenyl-3H-1,3-thiazol-2-ol (enol) has been carried out. To determine lowest-energy molecular conformation of the title molecule, the selected torsion angles were varied in steps of 10° and molecular energy profile was calculated from −180° to +180°. Experimental FT-IR and FT-Raman spectra of title compound were compared with the spectral data obtained by DFT/B3LYP method. Dipole moment, polarizability, first static hyperpolarizability and molecular electrostatic potential surface map have been calculated to get a better insight of the properties of title molecule. Natural bond orbital (NBO) analysis has been done to study the stability of the molecule arising from charge delocalization. UV–Vis spectrum of the title compound was also recorded and electronic properties such as frontier orbitals and band gap energies were calculated by TD-DFT approach. To compare the drug efficacy of enolic and keto forms, QSAR properties of both forms have also been computed and discussed.