SYNTHESIS, CRYSTAL STRUCTURES AND ANTIBACTERIAL ACTIVITIES OF BENZOHYDRAZONE DERIVATIVES FROM 4-DIETHYLAMINOSALICYLALDEHYDE

SYNTHESIS, CRYSTAL STRUCTURES AND ANTIBACTERIAL ACTIVITIES OF BENZOHYDRAZONE DERIVATIVES FROM 4-DIETHYLAMINOSALICYLALDEHYDE

A series of three new benzohydrazone compounds, C18H21N3O3 (1), C19H23N3O3 (2), and C18H20ClN3O2 (3), derived from the condensation of 4-diethylaminosalicylaldehyde with 2-hydroxybenzohydrazide, 4-methoxybenzohydrazide, and 4-chlorobenzohydrazide, respectively, in methanol, were prepared. The compou...

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Autores principales: WANG,ZHIGANG, ZHI,FENG, WANG,RONG, XUE,LIAN, ZHANG,YI, WANG,QIANG, YANG,YI-LIN
Lenguaje:English
Publicado: Sociedad Chilena de Química 2013
Materias:
benzohydrazone
crystal structure
X-ray diffraction
antibacterial activity
hydrogen bonds
Acceso en línea:http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200027
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Sumario:A series of three new benzohydrazone compounds, C18H21N3O3 (1), C19H23N3O3 (2), and C18H20ClN3O2 (3), derived from the condensation of 4-diethylaminosalicylaldehyde with 2-hydroxybenzohydrazide, 4-methoxybenzohydrazide, and 4-chlorobenzohydrazide, respectively, in methanol, were prepared. The compounds were characterized by elemental analysis, IR spectra, ¹H NMR spectra, and single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group P2(1) with unit cell dimensions a = 6.2656(6) Å, b = 21.873(2) Å, c = 6.6362(7) Å, β = 114.025(2)°, V = 830.70(15) ų, Z = 2, R1 = 0.0323 and wR2 = 0.0784. Compound 2 crystallizes in the monoclinic space group P2(1)/c with unit cell dimensions a = 13.8966(17) Å, b = 13.1402(15) Å, c = 9.8043(12) Å, β = 90.768(2)°, V = 1790.1(4) ų, Z = 4, R1 = 0.0670 and wR2 = 0.1671. Compound 3 crystallizes in the triclinic space group P-1 with unit cell dimensions a = 9.884(2) Å, b = 11.781(3) Å, c = 15.990(4) Å, α = 95.916(5)°, β = 99.520(5)°, γ = 104.147(4)°,V = 1760.5(7) ų, Z = 4, R1 = 0.0698 and wR2 = 0.1250. Crystal structures of the compounds are stabilized by hydrogen bonds and π · π stacking interactions. The preliminary antibacterial tests against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, and Candida albicans were assayed.

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