Synthesis, Crystal Structures, and Antibacterial Activity of Two Hydrazone Derivatives 3-Methoxy-N′-(3,5-Dibromo-2-Hydroxybenzylidene)Benzohydrazide Methanol Solvate and 3-Methoxy-N′-(2,4-Diclorobenzylidene)Benzohydrazide

Abstract

Two new hydrazone compounds with the formulae C₁₅H₁₂Br₂N₂O₃·CH₃OH (1) and C₁₅H₁₂Cl₂N₂O₂ (2), were prepared and characterized by elemental analysis, IR spectra and single-crystal X-ray determination. Compound (1) crystallizes in the triclinic space group P-1 with unit cell dimensions a = 7.654(1) Å, b = 13.801(2) Å, c = 16.904(2) Å, α = 90.772(2)^o, β = 101.721(2)^o, γ = 95.891(2)^o, V = 1738.1(4) Ǻ³, Z = 4, R ₁ = 0.0495 and wR ₂ = 0.1161. Compound (2) crystallizes in the triclinic space group P-1 with unit cell dimensions a = 8.296(1) Å, b = 12.987(2) Å, c = 14.121(2) Å, α = 88.922(2)^o, β = 87.960(2)^o, γ = 84.130(2)^o, V = 1512.3(4) Ǻ³, Z = 4, R ₁ = 0.0526 and wR ₂ = 0.1220. The single crystal structure analysis indicates that compound (1) consists of two nearly coplanar hydrazone molecules and two methanol molecules which link to the hydrazone molecules through O–H···O hydrogen bonds, while compound (2) consists of two independent distorted hydrazone molecules. In the crystal structure of (1), adjacent two hydrazone molecules are linked with methanol molecules through intermolecular hydrogen bonds of O–H···O and N–H···O, forming a dimer. In the crystal structure of (2), molecules are linked through intermolecular N–H···O hydrogen bonds, forming chains running along the a axis.

Index Abstract

Two new hydrazone derivatives were prepared and characterized by elemental analysis, IR spectra and single-crystal X-ray determination. Both structures are stabilized by intermolecular O–H···O and/or N–H···O hydrogen bonds and weak π···π interactions. The biological tests indicate that both compounds are excellent antibacterial materials.