Experimental and Theoretical Investigations of 4-Chloro Benzamidoxime

Abstract

4-Chloro-N-(2-methoxyphenyl) benzamidoxime (CMB) has been synthesized and characterized by X-ray diffraction, 1H NMR, 13C NMR, FT-IR and FT-Raman spectra. The X-ray study showed that CMB has a Z configuration, due to the strong intramolecular NHâ̄O hydrogen bond and centrosymmetric dimer form due to intermolecular OHâ̄N′ and OHâ̄O′ 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 1H and 13C 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, 1H NMR and 13C NMR spectra properties. © 2013 Elsevier B.V. All rights reserved.