5-Hydroxy-8-nitro-1,4-naphthoquinone
نویسندگان
چکیده
The title compound, C(10)H(5)NO(5), features an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring with an S(6) ring motif. The nitro group makes a dihedral angle of 71.66 (5)° with the plane of the benzene ring to which it is bound. The two rings are almost coplanar, with a dihedral angle of 4.44 (5)°. Short inter-molecular distances between the centroids of the six-membered rings [3.7188 (6)-3.8299 (6) Å] indicate the existence of π-π inter-actions. The inter-esting features of the crystal structure are the short inter-molecular O⋯O and O⋯N inter-actions. The crystal packing is stabilized by intra-molecular O-H⋯O and inter-molecular C-H⋯O (×3) hydrogen bonds, and C-H⋯π inter-actions.
منابع مشابه
A new method for the synthesis of juglone
In the present study, an appropriate synthetic route was adopted to produce the target synthesis of Juglone. In the first of these objectives, 5-nitro-1,4-naphthoquinone had been synthesized by direct nitration of 1,4-naphthoquinone in the presence of water and sulfuric acid. Then the intermediate synthesis of 5-amino-1,4-naphthoquinone was obtained by the reduction of nitro. Finally, Juglone w...
متن کامل5-Chloro-8-hydroxy-6-methyl-1,4-naphthoquinone
The mol-ecule of the title compound, C(11)H(7)ClO(3), is planar, with a maximum deviation of 0.0383 (10) Å from the naphthoquinone plane. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds. Short intra-molecular Cl⋯O [2.8234 (8) Å] and O⋯O [2.5530 (11) Å], and inter-molecular Cl⋯Cl [3.2777 (3) Å] contact...
متن کاملFormation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone
From the treatment of 5-hydroxy-1,4-naphthoquinone (juglone) with acetic anhydride and H2SO4 followed subsequently by treatment with methanolic HCl, 5-hydroxy-3-methoxy-1,4-naphthoquinone (3-methoxy juglone) and 8-hydroxy-4-methoxy-1,2-naphthoquinone were obtained as products rather than the anticipated product 2,5-dihydroxy-1,4-naphthoquinone (2-hydroxy juglone). The reaction and the identific...
متن کاملIn vitro antimicrobial activity of a new series of 1,4-naphthoquinones.
The antibacterial activity of a series of 1,4-naphthoquinones was demonstrated. Disk diffusion tests were carried out against several Gram-positive and Gram-negative bacteria. The compound 5-amino-8-hydroxy-1,4-naphthoquinone was the most effective, presenting inhibition zones measuring 20 mm against staphylococci, streptococci and bacilli at 50 microg/ml. Methicillin-resistant Staphylococcus a...
متن کاملEffect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes.
The effect of hydroxy substitution on 1,4-naphthoquinone toxicity to cultured rat hepatocytes was studied. Toxicity of the quinones decreased in the series 5,8-dihydroxy-1,4-naphthoquinone greater than 5-hydroxy-1,4-naphthoquinone greater than 1,4-naphthoquinone greater than 2-hydroxy-1,4-naphthoquinone, and intracellular GSSG formation decreased in the order 5,8-dihydroxy-1,4-naphthoquinone gr...
متن کامل