Conformation stability, halogen and solvent effects on C = O stretching of 4-chloro-3-halogenobenzaldehydes


Tursun M., Parlak C.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, cilt.141, ss.58-63, 2015 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 141
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.saa.2015.01.023
  • Dergi Adı: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
  • Sayfa Sayıları: ss.58-63

Özet

The effects of halogen and solvent on the conformation and carbonyl stretching of 4-chloro-3-halogenobenzaldehydes [C7H4ClXO; X = F (CFB), Cl (CCB) or Br (CBB)] were investigated using the density functional theory (DFT) method. The B3LYP functional was used by the 6-311+G(3df,p) basis set in combination with the polarizable continuum model (PCM). Computations were focused on the cis and trans isomers of the compounds in 18 different polar or non-polar organic solvents. The theoretical frequencies of the solvent-induced C=O stretching vibrations were correlated with the empirical solvent parameters such as the Kirkwood-Bauer-Magat (KBM) equation, the solvent acceptor number (AN), Swain parameters and the linear solvation energy relationships (LSER). The present work explores the effect of both the halogen and medium on the conformational preference and C=O vibrational frequency. The findings of this work can be useful to those systems involving changes in the conformations analogous to the compounds studied. (C) 2015 Elsevier B.V. All rights reserved.