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Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination

p-Toluic hydrazide was used for synthetizing a new Schiff base N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide (I). The prepared compound was characterized by elemental analysis, infrared and 1H and 13C NMR spectroscopy techniques, and the structure of compound (I) was determined by single-crystal X-ray diffraction study. The compound (C15H14N2O3) crystallises in the monoclinic space group P21/n with the following unit cell parameters: a = 11.7820 (6) Å, b = 8.5278 (4) Å, c = 13.6054 (7) Å, β = 109.346 (5)°, V = 1289.81 (12) Å3, Z = 4, R1 = 0.071 and wR2 = 0.197. The X-ray structure shows that the compound (I) adopts an E configuration with respect to the double bond C7=N1. The carbonyl oxygen atom O3 and the nitrogen atom N1 of the hydrazide moiety are in a syn conformation with respect to C8—N2 bond. The crystal packing of compound (I) is stabilized by intramolecular O(phenol)–H•••N(carbohydrazide) which results in an S(6) ring motif and intermolecular O(phenol)–H•••O(carbohydrazide) hydrogen bonds which form chains. The carbonohydrazide moiety C=N–N–C(O)–N–N=C fragment is almost coplanar with the two benzene rings with dihedral angles of their mean planes of 10.35° [C1—C6] and 7.99° [C9—C14], respectively. The dihedral angle between the mean planes of the phenyl rings is 2.46°.

Schiff Base, 2,3-dihroxybenzaldehyde, p-toluic Hydrazide, Single Crystal Structure

APA Style

Alioune Fall, Mohamedou El Boukhary, Thierno Mousa Seck, Farba Bouyagui Tamboura, Ibrahima Elhadj Thiam, et al. (2023). Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination. Modern Chemistry, 11(2), 43-48.

ACS Style

Alioune Fall; Mohamedou El Boukhary; Thierno Mousa Seck; Farba Bouyagui Tamboura; Ibrahima Elhadj Thiam, et al. Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination. Mod. Chem. 2023, 11(2), 43-48. doi: 10.11648/

AMA Style

Alioune Fall, Mohamedou El Boukhary, Thierno Mousa Seck, Farba Bouyagui Tamboura, Ibrahima Elhadj Thiam, et al. Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination. Mod Chem. 2023;11(2):43-48. doi: 10.11648/

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