The molecular structure and vibrational spectra of N-(2,2-diphenylacetyl)-N'-(naphthalen-1yl)-thiourea by Hartree-Fock and density functional methods

Spectrochim Acta A Mol Biomol Spectrosc. 2009 Apr;72(3):561-71. doi: 10.1016/j.saa.2008.10.049. Epub 2008 Nov 11.

Abstract

N-(2,2-Diphenylacetyl)-N'-(naphthalen-1yl)-thiourea (PANT) has been synthesized and characterized by elemental analysis, IR spectroscopy and (1)H NMR spectroscopy. The crystal and molecular structure of the title compound has been determined from single crystal X-ray diffraction data. It crystallizes in the triclinic space group P-1, Z=2 with a=10.284(2)A, b=10.790(2)A, c=11.305(2)A, alpha=64.92(3) degrees , beta=89.88(3) degrees , gamma=62.99(3) degrees , V=983.7(3)A(3) and D(calc)=1.339Mg/m(3). The molecular structure, vibrational frequencies and infrared intensities of PANT were calculated by the Hartree-Fock and density functional theory methods (BLYP and B3LYP) using the 6-31G* basis set. The calculated geometric parameters were compared to the corresponding X-ray structure of the title compound. We obtained 22 stable conformers for the title compound; however Conformer 1 is approximately 9.53kcal/mol more stable than Conformer 22. The comparison of the theoretical and experimental geometry of the title compound shows that the X-ray parameters fairly well reproduce the geometry of Conformer 17. The harmonic vibrations computed for this compound by the B3LYP/6-31G* method are in good agreement with the observed IR spectral data. Theoretical vibrational spectra of the title compound were interpreted by means of PEDs using the VEDA 4 program. A general better performance of the investigated methods was calculated by PAVF 1.0 program.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallization
  • Hydrogen Bonding
  • Least-Squares Analysis
  • Magnetic Resonance Spectroscopy / methods
  • Models, Molecular
  • Molecular Structure
  • Naphthalenes / chemistry
  • Spectrophotometry, Infrared / methods
  • Spectroscopy, Fourier Transform Infrared
  • Spectrum Analysis / methods*
  • Temperature
  • Thiourea / chemical synthesis
  • Thiourea / chemistry*
  • Vibration*
  • X-Ray Diffraction

Substances

  • N-(2,2-diphenylacetyl)-N'-(naphthalen-1yl)-thiourea
  • Naphthalenes
  • Thiourea