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, H-1 NMR, C-13 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 center dot center dot center dot O hydrogen bond and centrosymmetric dimer form due to intermolecular O-H center dot center dot center dot N' and O-H center dot center dot center dot 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)degrees, respectively. The optimized molecular structure and vibrational frequencies have been calculated with OFT (B3LYP) method by using a 6-311G(d,p) basis set. The H-1 and C-13 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, H-1 NMR and C-13 NMR spectra properties. (C) 2013 Elsevier B.V. All rights reserved.