Synthesis, molecular structure, FT-IR and XRD investigations of 2-(4-chlorophenyl)-2-oxoethyl 2-chlorobenzoate: a comparative DFT study

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 24:124:595-602. doi: 10.1016/j.saa.2014.01.063. Epub 2014 Jan 23.

Abstract

2-(4-Chlorophenyl)-2-oxoethyl 2-chlorobenzoate has been synthesized, its structural and vibrational properties have been reported using FT-IR and single-crystal X-ray diffraction (XRD) studies. The conformational analysis, optimized geometric parameters, normal mode frequencies and corresponding vibrational assignments of the synthesized compound (C15H10Cl2O3) have been examined by means of Becke-3-Lee-Yang-Parr (B3LYP) density functional theory (DFT) method together with 6-31++G(d,p) basis set. Furthermore, reliable conformational investigation and vibrational assignments have been made by the potential energy surface (PES) and potential energy distribution (PED) analyses, respectively. Calculations are performed with two possible conformations. The title compound crystallizes in orthorhombic space group Pbca with the unit cell dimensions a=12.312(5) Å, b=8.103(3) Å, c=27.565(11) Å, V=2750.0(19) Å(3). B3LYP method provides satisfactory evidence for the prediction of vibrational wavenumbers and structural parameters.

Keywords: Crystal structures; DFT; Infrared spectra; Phenacyl bromide; XRD.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chlorobenzoates / chemical synthesis*
  • Chlorobenzoates / chemistry
  • Hydrogen Bonding
  • Models, Molecular*
  • Molecular Conformation
  • Quantum Theory*
  • Spectroscopy, Fourier Transform Infrared
  • Thermodynamics
  • X-Ray Diffraction*

Substances

  • Chlorobenzoates