Synthesis, structural, vibrational and quantum chemical investigations of N-(2-methylphenyl)-2,2-dichloroacetamide and N-(4-methylphenyl)-2,2-dichloroacetamide

Spectrochim Acta A Mol Biomol Spectrosc. 2009 Oct 15;74(3):607-16. doi: 10.1016/j.saa.2009.07.008. Epub 2009 Jul 15.

Abstract

N-(2-Methylphenyl)-2,2-dichloroacetamide (2MPA) and N-(4-methylphenyl)-2,2-dichloroacetamide (4MPA) of the configuration X(y)C(6)H(5-y)-NHCO-CHCl(2) (where, X=CH(3) and y=1) were synthesised and an extensive spectroscopic investigations have been carried out by recording the Fourier transform infrared (FTIR) and FT-Raman spectra and subjecting them to normal co-ordinate analysis, in an effort to provide mixing of the fundamental modes with the help of potential energy distribution (PED). The ab initio and DFT studies were carried out with 6-311++G(d,p) basis set to determine the structural, thermodynamical and vibrational characteristics of the compounds and also to understand the steric influence of methyl group on the characteristic frequencies of amide (-CONH-) group.

MeSH terms

  • Acetamides / chemical synthesis
  • Acetamides / chemistry*
  • Dicarboxylic Acids
  • Molecular Structure
  • Quantum Theory*
  • Spectroscopy, Fourier Transform Infrared
  • Spectrum Analysis, Raman

Substances

  • 2-methylenepentanedioic acid
  • Acetamides
  • Dicarboxylic Acids
  • N-(4-methylphenyl)-2,2-dichloroacetamide