Crystallographic, spectroscopic (FTIR and NMR) and quantum computational calculation studies on bis(2-methoxy-4-((E)-prop-1-enyl)phenyl)oxalate

Ersanli C. C., KANTAR G. K., Sasmaz S.

JOURNAL OF MOLECULAR STRUCTURE, vol.1143, pp.318-327, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1143
  • Publication Date: 2017
  • Doi Number: 10.1016/j.molstruc.2017.04.032
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.318-327
  • Keywords: Crystal structure, DFT, HF, Oxalate, Spectral analysis, MOLECULAR-STRUCTURE, MONOCYTOGENES, INHIBITION, CONTINUUM
  • Recep Tayyip Erdoğan University Affiliated: Yes


In this paper, we report first, a new synthesis of bis(2-methoxy-4-((E)-prop-1-enyl)phenyl)oxalate, namely, C22H22O6, (I). Then, we present detailed FTIR, H-1 NMR,C-13 NMR spectroscopies and single-crystal X-ray diffraction techniques, Hartree-Fock (HF) and Density Functional Theory (DFT) molecular orbital calculation study of the title compound. Compound (I) crystallizes in the monoclinic space group P2(1)/c, with Z = 2 in cells with a = 6.3440(5)angstrom, b = 10.1098(9)angstrom, c = 16.1899(15)angstrom, V = 1035.65(16)angstrom(3) and displays weak C-H center dot center dot center dot O intermolecular interaction which contributes to crystal packing. The molecular geometry was also calculated using the Gaussian03W software, and structure was optimized using the HF and DFT/B3LYP methods with the 6-31G(d,p) basis set at the ground state. The harmonic vibrational frequencies, H-1 and C-13 NMR chemical shifts of I were calculated using the same method with the 6-31G(d,p) basis set. The calculated results show that the predicted geometry can well reproduce structural parameters. The energetic behaviors of the title compound in solvent media were examined using the DFT/B3LYP method with the 6-31G(d,p) basis set applying the Polarizable Continuum Model (PCM). Besides, the frontier molecular orbitals (FMOs), Mulliken population method, natural population analysis (NPA), molecular electrostatic potential (MEP) map of the title compound were investigated by theoretical calculations. Based on vibrational analyses, the thermodynamic properties of I at different temperatures have been calculated, and corresponding relations between the properties and temperature have also been obtained. (C) 2017 Elsevier B.V. All rights reserved.