Mohammed Hadi Al–Douh(1*), Shafida Abd Hamid(2), Hasnah Osman(3)

(1) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang, Malaysia
(2) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang, Malaysia
(3) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang, Malaysia
(*) Corresponding Author


The reaction of Benzyl o-vanillin 1 and o-phenylene diamine 2 in dichloromethane produced new benzimidazole, 3. The complete assignments of 3 were made using 1D and 2D NMR including COSY, HMQC and HMBC NMR in CDCl3 and acetone-d6. The coupling constants J are reported in Hertz, and the differences in the peak splittings using both solvents are discussed.


1H NMR; 13C NMR; 2D NMR; Benzimidazole

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[34] Crystal data of 3: C21H18N2O2, Mr = 330.37, monoclinic, P21/c, a = 9.54170 (1), b = 18.4590 (3), c = 11.0653 (2) Å, b = 123.814 (1)o, V = 1619.27 (4) Å3, Z = 4, m = 0.088 mm–1, dx = 1.355 g cm–3, F(000) = 696, GOF = 1.062. A total of 54869 reflections were collected and 8446 are unique (Rint = 0.0539), R = 0.0501, wR = 0.1282 for 227 parameters and 8446 reflections (I > 2s (I)). Residual electron density extremes were 0.613 and –0.326 e Å–3. The intensity data was collected at 297 K on SMART APEX2 CCD area–detector diffractometer with graphite–monochromated MoKa radiation (0.71073 Å), q range 2.21 to 37.50o [38]. All absorption corrections were performed by using SADABS the multiscan program [38]. The structure was solved and refined by SHELXTL against F2[39]. The H atoms were refined as riding and the Uiso values were freely refined, they were placed in calculated positions, with C–H = 0.93–0.97 Å and N–H = 0.89 Å. The software was used SHELXTL [39] and PLATON [40]. These data can be obtained free of charge from International Union of Crystallography IUCr cv2101 or The Cambridge Crystallographic Data Centre CCDC 620951. Reference: (doi:10.1107/S160053680603251X).

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DOI: https://doi.org/10.22146/ijc.21697

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