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

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...

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Autor principal:	HAN,YOU-YUE
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2013
Materias:	Synthesis crystal structure benzohydrazone hydrogen bonds antimicrobial activity
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000300014
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spelling	oai:scielo:S0717-970720130003000142014-09-09CRYSTAL 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 SOLVATEHAN,YOU-YUE Synthesis crystal structure benzohydrazone hydrogen bonds antimicrobial activity 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.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.58 n.3 20132013-09-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000300014en10.4067/S0717-97072013000300014
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Synthesis crystal structure benzohydrazone hydrogen bonds antimicrobial activity
spellingShingle	Synthesis crystal structure benzohydrazone hydrogen bonds antimicrobial activity HAN,YOU-YUE 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
description	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.
author	HAN,YOU-YUE
author_facet	HAN,YOU-YUE
author_sort	HAN,YOU-YUE
title	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
title_short	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
title_full	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
title_fullStr	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
title_full_unstemmed	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
title_sort	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
publisher	Sociedad Chilena de Química
publishDate	2013
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000300014
work_keys_str_mv	AT hanyouyue crystalstructuresandantimicrobialactivitiesofn25dihydroxybenzylidene345trimethoxybenzohydraziden24dichlorobenzylidene345trimethoxybenzohydrazideand24dichloron2hydroxy3methoxy5nitrobenzylidenebenzohydrazideethanolsolvate
_version_	1718445493209530368

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

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