Synthesis, structural characterization and computational studies of (E)-4-bromo-2-((3-chlorophenylimino)methyl)-6-ethoxyphenol

Abstract

The present work reports on synthesis, single crystal X-ray diffraction, FT-IR, Uv–Vis., 1H and 13C NMR and theoretical calculations of the (E)-4-bromo-2-((3-chlorophenylimino)methyl)-6-ethoxyphenol compound. This study mainly focused on prototropic tautomerism and intramolecular proton transfer of (E)-4-bromo-2-((3-chlorophenylimino)methyl)-6-ethoxyphenol in solvent media and in solid state. X-ray and FT-IR studies clearly reveals that the title compound exist in the enol form in solid state. Due to the dependence of prototropic tautomerism on solvent types, UV–Vis. spectra of the title compound were recorded in benzene, in chloroform and in ethanol. With the aid of theoretical calculations, important bands in the electronic spectrum were defined by means of frontier molecular orbitals. Intramolecular proton transfer process on the O–H…N hydrogen bond and transition state structure during the transfer process were investigated by scan calculations in the vacuum and in the different solvents. 1H and 13C NMR spectra were recorded in CDCl3 and detailed interpretation have been made on the basis of the theoretical calculations. Also, the stabilization energies of the title compound were computed by using second-order perturbation theory in order to investigate the intra- and inter-molecular interactions, interaction among bonds, conjugative interactions. Nonlinear optical property calculations of the compound indicate that the material can be used as a NLO material.