CRYSTAL STRUCTURES AND ANTIMICROBIAL ACTIVITIES OF N'-[2,5-DIHYDROXYBENZYLIDENE]-3,4,5-TRIMETHOXYBENZOHYDRAZIDE, N'-[2,4-DICHLOROBENZYLIDENE]-3,4,5-TRIMETHOXYBENZOHYDRAZIDE, AND 2,4-DICHLORO-N'-(2-HYDROXY-3-METHOXY-5-NITROBENZYLIDENE)BENZOHYDRAZIDE ETHANOL SOLVATE

• Published in: Journal of the Chilean Chemical Society Vol. 58; no. 3; pp. 1858 - 1861
• Main Author: HAN, YOU-YUE
• Format: Journal Article
• Language: English
• Published: Sociedad Chilena de Química 01.09.2013
• Subjects: CHEMISTRY, MULTIDISCIPLINARY; crystal structure; benzohydrazone; Synthesis; antimicrobial activity; hydrogen bonds
• ISSN: 0717-9707; 0717-9707
• DOI: 10.4067/S0717-97072013000300014

Three benzohydrazone compounds, N'-[2,5-dihydroxybenzylidene]-3,4,5-trimethoxybenzohydrazide (1), N'-[2,4-dichlorobenzylidene]-3,4,5-trimethoxybenzohydrazide (2), and 2,4-dichloro-N'-(2-hydroxy-3-methoxy-5-nitrobenzylidene)benzohydrazide ethanol solvate (3), have been synthesized and structurally characterized by elemental analysis and X-ray single crystal structure determination. Compound (1) crystallizes in the orthorhombic space group Pbca, with unit cell dimensions a = 15.193(2), b = 11.086(2), c = 20.203(3) Å, V = 3402.8(8) Å3, Z = 8. Compound (2) crystallizes in the monoclinic space group P2(1)/c, with unit cell dimensions a = 17.127(3), b = 13.326(3), c = 7.984(2) Å, β = 99.689(2)°, V = 1796.2(6) Å3, Z = 4. Compound (3) crystallizes in the monoclinic space group P2(1)/n, with unit cell dimensions a = 12.919(3), b = 10.068(2), c = 15.205(4) Å, β = 98.288(2)°, V = 1957.0(7) Å3, Z = 4. X-ray crystallography reveals that each compound has an E configuration with respect to the C=N double bond and C-N single bond. The molecular structures of the compounds are stabilized by hydrogen bonds and weak πˑˑˑ π stacking interactions. The antimicrobial activities against Bacillus subtilis, Escherichia coli, Staphyloccocus aureus, and Bacillus magaterium were studied. The electron-withdrawing groups, such as Cl and NO2 are preferred groups for the antimicrobial material. Among the compounds, (3) showed the most effective activity against Escherichia coli, which is even stronger than the controlled drug Tetracycline.