Determination of structural, spectrometric and nonlinear optical features of 2-(4-hydroxyphenylazo)benzoic acid by experimental techniques and quantum chemical calculations

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 105; pp. 80 - 87
• Main Authors: Cinar, Mehmet, Yildiz, Nihat, Karabacak, Mehmet, Kurt, Mustafa
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 15.03.2013
• Subjects: 2-(4-Hydroxyphenylazo)benzoic acid; Azo Compounds - chemistry; Magnetic Resonance Spectroscopy; Models, Molecular; Quantum chemical calculations; Quantum Theory; Spectroscopic characterization; Spectroscopy, Fourier Transform Infrared; Spectrum Analysis, Raman; Quantum chemical calculations; 2-(4-Hydroxyphenylazo)benzoic acid; Spectroscopic characterization
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2012.12.009

[Display omitted] ► Ground state molecular structure of HABA molecule was optimized. ► Vibrational spectra were examined via FT-IR and FT-Raman techniques and DFT method. ► Electronic transitions were investigated in different solvents. ► Chemical shift were determined depending on predicted and recorded NMR spectra. ► NLO properties were studied theoretically. The optimized geometrical structure, vibrational and electronic transitions, chemical shifts and nonlinear optical properties of 2-(4-hydroxyphenylazo)benzoic acid (HABA) compound were presented in this study. The ground state geometrical structure and vibrational wavenumbers were carried out by using density functional (DFT/B3LYP) method with 6-311++G(d,p) basis set. The vibrational spectra of title compound were recorded in solid state with FT-IR and FT-Raman spectrometry in the range of 4000–400cm−1 and 4000–10cm−1; respectively. The fundamental assignments were done on the basis of the recorded spectra and total energy distribution (TED) of the vibrational modes. The 1H and 13C NMR spectra were recorded in deuterated DMSO solution, and gauge–invariant atomic orbitals (GIAOs) method was used to predict the isotropic chemical shifts. The UV–Vis absorption spectra of the compound were observed in the range of 200–800nm in ethanol, methanol and water solvents. To investigate the nonlinear optical properties, the polarizability, anisotropy of polarizability and molecular first hyperpolarizability were computed. A detailed description of spectroscopic behaviors of compound was given based on the comparison of experimental measurements and theoretical computations.