Experimental and theoretical investigations of 4-chloro-N-(2-methoxyphenyl)benzamidoxime

Abstract

4-Chloro-N-(2-methoxyphenyl) benzamidoxime (CMB) has been synthesized and characterized by X-ray diffraction, (1)H NMR, (13)C NMR, FT-IR and FT-Raman spectra. The X-ray study showed that CMB has a Z configuration, due to the strong intramolecular N-H···O hydrogen bond and centrosymmetric dimer form due to intermolecular O-H···N' and O-H···O' hydrogen bonds. The 2-methoxyphenyl and 4-chlorophenyl rings are twisted from the mean plane of the hydroxyamidine group by 33.09 (1) and 44.89 (1)°, respectively. The optimized molecular structure and vibrational frequencies have been calculated with DFT (B3LYP) method by using a 6-311G(d,p) basis set. The (1)H and (13)C NMR chemical shifts were calculated by the gauge-including atomic orbital (GIAO) method with the B3LYP/6-311G (d,p) level. A comparison between experimental and calculated theoretical results indicate that the density functional B3LYP method provided satisfactory results for predicting IR, Raman, (1)H NMR and (13)C NMR spectra properties.