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

• The crystal structure analysis of 4-chloro-N-(2-methoxyphenyl)benzamidoxime by using X-ray crystallography.
• In the crystal structure, the CMB configuration is Z since OH group is in the same direction NH group.
• The calculated NMR chemical shifts and vibrational frequencies are in good accordance with experimental values.

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 NH⋯O hydrogen bond and centrosymmetric dimer form due to intermolecular OH⋯N′ and OH⋯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 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.

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