Citation: WEN Hui-Liang, KANG Jing-Jing, DAI Bing, DENG Rui-Hong, HU Hai-Wei. Syntheses, Crystal Structures and Antibacterial Activities of 5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic Acid and Its Copper(Ⅱ) Compound[J]. Chinese Journal of Structural Chemistry, ;2015, 34(1): 33-40. doi: 10.14102/j.cnki.0254-5861.2011-0447 shu

Syntheses, Crystal Structures and Antibacterial Activities of 5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic Acid and Its Copper(Ⅱ) Compound

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a. State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China;
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b. China Petroleum Technology & Development Corporation, Beijing 100028, China;
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c. Department of Chemistry, Nanchang University, Nanchang 330031, China

Received Date: 9 July 2014
Available Online: 9 September 2014
Fund Project: Supported by the National Natural Science Foundation of China (No. 20662007) (No. 20662007) the Bureau of Education of Jiangxi Province (No. GJJ09064) (No. GJJ09064)

The title compounds 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid (C₁₁H₉ClN₂O₂, HL) (1) and [Cu(L)₂(H₂O)] (2) were prepared and structurally characterized by elemental analysis, IR and single-crystal X-ray diffraction. Compound 1 (C₁₁H₉ClN₂O₂) crystallizes in the monoclinic system, space group P2₁/n with a=7.249(3), b=20.515(10), c=7.249(3), β=96.30°, V=1071.6(9)Å³, Z=4, M_r=236.65, D_c=1.467 g/cm³, F(000)=488, GOOF=1.029, μ=0.341 mm^-1, the final R=0.0736 and wR=0.1966 for 1500 observed reflections with I>2σ(I). Compound 2 (C₂₂H₁₈Cl₂CuN₄O₅) crystallizes in the monoclinic system, space group P2₁/c with a=7.2931(6), b=24.548(2), c=13.2726(11), β=99.4040(10)°, V=2344.2(3)Å³, Z=4, M_r=552.84, D_c=1.566 g/cm³, F(000)=1124, GOOF=1.050, μ=1.201 mm^-1, the final R=0.0376 and wR=0.1000 for 3626 observed reflections with I>2σ(I). 1 and 2 are connected through hydrogen bonding interactions to generate 2D and 3D supramolecular structures, respectively. Moreover, the preliminary antibacterial activities of 1 and 2 against the gram positive bacteria (S. aureus, C. albicans and B. subtilis) and gram negative bacteria (E. coli and P. aeruginosa) have been tested by using the microdilution method, and the results indicate that 2 is more active than 1 against the tested bacteria.
- pyrazole carboxylic acid,
- copper compound,
- helix chain,
- crystal structure,
- antibacterial activity
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