Benzoylacetone Research Articles

Crystal structure and Hirshfeld surface analysis of bis-(benzoyl-acetonato)(ethanol)dioxidouranium(VI).

A new uranium metal-organic complex salt, [U(C10H9O2)2O2(C2H6O)], with benzoyl acetone, namely, bis-(benzoyl-acetonato)(ethanol)dioxidouranium(VI), was synthesized. The compound has monoclinic P21/n symmetry. The geometry of the seven-coordinate U atom is penta-gonal bipyramidal, with the uranyl oxygen atoms in apical positions. In the complex, the ligands bind to the metal through oxygen atoms. Additional weak O-H⋯O contacts between the cations and anions consolidate the three-dimensional arrangement of the structure. On the Hirshfeld surface, the largest contributions come from the short contacts such as van der Waals forces, including H⋯H, O⋯H and C⋯H. Inter-actions including C⋯C and O⋯C contacts were also observed; however, their contribution to the overall cohesion of the crystal structure is minor. A packing analysis was performed to check the strength of the crystal packing.

6-Polyfluoroalkyl-1-arylhexane-1,3,5-triones: Syntheses, ring-chain tautomerism and dehydrative cyclization to 6-polyfluoroalkyl-1-arylpyran-4H-ones

In this work, we present a synthetic protocol for the synthesis of non-symmetrical fluoroalkylated triketones. The synthesis is based on the reaction of benzoyl acetones with esters in the presence of excess lithium hydride. The tautomeric equilibrium of triketones in CDCl3 and DMSO‑d6 solutions was studied. The synthetic application of 1,3,5-triketones has been demonstrated. A method has been developed for the efficient synthesis of 2-aryl-6-(polyfluoroalkyl)-4H-pyran-4-ones by dehydrative cyclization.

Structure, Tautomeric, and intramolecular hydrogen bond of Difluorobenzoylacetone; IR, UV, NMR, and quantum calculation studies

The molecular structure, tautomerism, spectroscopy properties, and intramolecular hydrogen bonding of 4,4-difluoro-1-phenyl-1,3-butanedione, also known as difluorobenzoylacetone (DFBA), have all been analyzed using density functional theory (DFT) calculations and spectroscopic techniques (IR, UV, and NMR). The results were compared with previously reported values for trifluorobenzoylacetone (TFBA) and benzoylacetone (BA). The energy difference between the two stable cis-enol forms,calculated at the B3LYP/6–311++G** level, is 0.96 kcal/mol.Therefore, the coexistence of both forms in comparable ratios is possible, as revealed by comparing the calculated and experimental vibrational band frequencies and their intensities. Furthermore,various computational methods were employed to examine the intramolecular hydrogen bond (IHB) strength and molecular stability,including geometry, atoms in molecules (AIM), and natural bond orbitals (NBO) theories. The hydrogen bond strength of DFBA falls between that of BA and TFBA, beinggreater than TFBA but lower than BA. Transition state study show that tautomerism between both forms occurs via the proton transfer.

Preparation and patterning of HfO2 film via sol–gel method and resistive switching effect of Pt/HfO2/LaNiO3

Sol–gel method is a low-cost material preparation method; however, it is difficult to obtain a stable sol containing easily hydrolyzable metal ions via this method. In this study, a stable hafnium(IV) oxide (HfO2) sol was prepared by adding benzoyl acetone (BzAcH) modifier. Infrared absorption spectroscopy results showed that the BzAcH additive chelated with the Hf4+ ions in the sol, thus improving the hydrolysis resistance of the HfO2 sol, which in turn improved its stability. It was also found that the BzAcH-modified HfO2 gel film exhibited ultraviolet (UV) photosensitivity. After UV exposure, the film did not dissolve easily in organic solvents. Based on these properties, the micro processing of the HfO2 film was preliminarily explored, and HfO2 microstructures were successfully obtained. Additionally, the relative permittivity (εr) of HfO2 exhibited minimum (∼10.9) and maximum (∼20.6) values at heat-treatment (HT) temperatures of 350 and 450 °C, respectively. With the continuous increase in the HT temperature, εr first decreased and then increased slightly. Moreover, the current–voltage curves showed that the Pt/HfO2/LaNiO3 (LNO) structure exhibited a pronounced bipolar resistive switching (RS) effect, which was attributed to the fact that LNO could be used as an electrode and an oxygen vacancy (OV2+) storage layer for RS materials. Notably, the oxygen ions in HfO2 with a low degree of crystallinity are more likely to migrate within its body (which makes it easier to form OV2+s), therefore, the “Set” voltage of low-crystallinity HfO2 films is lower than that of high-crystallinity HfO2 films. The RS mechanism can be explained by the OV2+ conductive filament model. These results are of great practical significance for the low-cost preparation of HfO2 and the application of LNO as an oxide electrode.

Design, synthesis, antimicrobial evaluation, molecular docking studies, and in silico prediction of ADME properties for novel pyrazolo[1,5‐a]pyrimidine and its fused derivatives

AbstractDienamine 2 was synthesized by reacting 5‐aminopyrazole 1 with two moles of (DMF DMA). Enamine 2 underwent subsequent reactions with various reagents in different reaction media, leading to the formation of distinct compounds. In an acidic environment, enamine 2 reacted with acetyl acetone, benzoyl acetone, dimedone, and ethyl acetoacetate, resulting in the synthesis of compounds 9a, 9b, 13, and 17, respectively. Conversely, in a basic medium, dienamine 2 combined with malononitrile, ethyl cyanoacetate, and malononitrile dimer, yielding compounds 21a, 21b, and 25. Moreover, by reacting with ammonium acetate in acetic acid, dienamine 2 produced compounds 28. The synthesized compounds underwent in vitro testing against various bacterial and fungal strains, revealing significant antibacterial activity against hazardous bacterial strains. To identify potential bacterial targets, an in‐silico study was initiated. Molecular docking investigations indicated that compound 25 exhibited the highest binding affinity toward dihydrofolate reductase and penicillin‐binding proteins. Furthermore, compound 25 demonstrated robust physiochemical properties, bioavailability, and drug‐like characteristics. These results collectively suggest the potential of compound 25 as a promising antibacterial agent with favorable drug properties.

Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study

Three 1-(n-pyridinyl)butane-1,3-diones (nPM) (n = 2, 3, and 4) molecules were synthesized and their molecular structure, tautomerism, conformational stability, and intramolecular hydrogen bonding (IHB) of cis-enol forms, was investigated by a combination of computational and experimental methods. Density functional theory (DFT) calculations were used and the Atoms in Molecules (AIM) analysis indicated an intramolecular hydrogen bond strength as 17.9–20.3 kcal/mol using the B3LYP/6–311++G(d,p) level of theory. The calculated structures, NBO, and intramolecular hydrogen bond strengths for the stable cis-enol forms of nPM molecules were compared with each other and with those of acetylacetone (AA) and benzoylacetone (BA). The single crystal X-ray structure of 4PM confirmed that the tautomer with the OH group next to the pyridine ring best describes the structure in the solid-state. The vibrational bands of the title molecules were assigned to the corresponding normal modes, and the equilibrium between the two cis enol tautomers was estimated by means of IR, Raman and UV/Vis spectroscopy.

Synthesis and characterization of Azo derivatives containing pyrazole ring

This research included the preparation of new pyrazole derivatives from the condensation of the benzoyl acetone with carboxylic acid hydrazide in ethanol as a solvent. The reaction included two steps from the tetra surfaces nucleophilic addition and cyclisation process in second step. The pyrazole derivatives products were reacted with Diazonium salts.
 The prepared compounds were characterized by infrared, Nuclear Magnatic resonance spectroscopy and the completing of the reaction was checking by the TLC.

Synthesis and Characterization of Heterocyclic Bicyclic from the Condensation of the Pyrazole Derivatives with Aldehydes and Ketones

The research included the preparation of new pyrazole derivatives from the condensation of the benzoyl acetone with carboxylic acid hydrazide in ethanal as a solvent. This reaction included two steps from the tetra surfaces nucleophilic addition and cyclisation process in second step. The pyrazole derivatives products were reacted with different aldehydes or ketones to give heterocyclic bicyclic compounds.
 The prepared compounds were characterized by infrared, and Nuclear Magnatic resonance spectroscopy and the completing of the reaction was characterized by thein.

J-V characteristics of sol-gel-prepared Zn2+ doped LiNbO3

Herein, a stable LiNbO3 (LN) sol, with different Zn2+ contents, is prepared using ethanol niobium, lithium acetate and zinc acetate as starting materials, absolute ethanol as a solvent, and acrylic acid and benzoyl acetone (BzAcH) as additives. The influence of Zn2+ content on LN crystal structure, light transmittance and J-V curve characteristics is studied in detail. XRD results reveal that Zn2+ doping, with a molar content of less than 5%, does not influence the crystal structure of LN. SEM indicates that the grain size of LN films gradually increases with the increase of doping content. The surface quality of LN films becomes worse when the doping content of Zn2+ reaches 5%. Moreover, light transmittance tests show that the maximum light transmittance is attained at the doping amount of 3%. J-V curves demonstrate that Pt/LN/LNO(LaNiO3) structure shows excellent resistance switching (RS) effect due to the formation of Schottky barrier at the Pt/LN interface, which initially becomes prominent with the increase of Zn2+ content, followed by a gradual decrease. On the other hand, In/LN/LNO structure exhibits poor RS effect due to the unobvious Schottky barrier at In/LNO interface. Furthermore, J-V curves at different temperatures demonstrate that the RS effect of Pt/LN/LNO structure tends to deteriorate, while the refractive index of LN film increases with the decrease of temperature. Herein, the abovementioned RS phenomenon is analyzed and explained in terms of the relationship between interfacial barrier and doping amount of Zn2+, migration of oxygen vacancies, and the relationship between insulation property of LN films and temperature. The research results are of experimental and theoretical significance for practical applications of LN films.

Synthesis and Biological Activity of Functionally Substituted Pyrimidine and Pyran Derivatives on the Basis of Isatylidene Malononitriles

AbstractIn this study, it was shown that pyrimidine and imidazopyridine derivatives were obtained from the multicomponent reaction of isatylidene malononitriles with malononitrile and diamines at room temperature. Also, the interaction of 2‐(5‐bromo‐2‐oxoindoline‐3‐ylidene)with malononitrile and benzoyl acetone (or ethyl‐4‐chlorine‐acetoacetate) was carried out and the formation of the corresponding pyran derivatives was observed.The structure of the synthesized compounds was confirmed by 1H, 13CNMR spectroscopy and X‐ray analysis. The acetylcholinesterase (AChE) inhibitor compounds recorded as important therapeutic drugs for the therapy of Alzheimer's disease. Also, novel complexes effectively inhibited AChE enzyme, with Ki values in the range of 4.56 to 8.21 μM. For this enzyme, it was obtained with IC50 values in the range of 4.04 to 9.85 μM. For α‐glycosidase enzyme the most effective Ki values were for 4 a and 10 compounds with Ki values of 31.48 and 32.63 μM, respectively. The molecular docking study was employedto investigate of chemical activities and interaction of synthesized compounds with low Ki in the presence of AChE, butyrylcholinesterase, and α‐Glycosidase. The results revealed that some of the compounds, like compound 9 have a good binding affinity to AChE with a docking score of −6.243 (kcal/mol). This compound can affect the enzyme activity by attachment to essential residues of the catalytic domain of the enzyme. The ADME/T analysis was also performed and revealed that compounds have the potential to be utilized as medicine.

Structural Exploration and Protein Binding Efficiencies of Binuclear Dioxidomolybdenum(VI) Complexes Constructed from ONO Chelator and Linear N−N Ditopic Spacer

Binuclear dioxido Mo(VI) complexes(1 and 2) of general formula [(MoO2L1−2)2(bpe)] have been synthesized by varying a auxiliary bridging ligand on the primary ligand framework. The impact of spacer variation on metal-organic supramolecular architectures, DFT calculations and BSA binding efficiencies of the complexes has been studied. The intermolecular interactions in the crystal structures are also studied by Hirshfeld surface analysis. FRET, Time-resolved fluorescence measurement and molecular docking of the complexes were also carried out.

Up-scalable preparation of nano zirconium carbide powder in liquid polymeric precursor and its pyrolysis mechanism

Nano size ZrC powder was prepared by liquid polymeric precursor method. Zirconium n-butoxide (Zr(O n Bu) 4 ) and benzoylacetone (BA) were mixed directly with different molar ratios to synthesize transparent liquid zirconium carbide single-source precursors. The carbon content in the precursor could be changed by adding different amount of BA. X-ray pure ZrC was obtained when the molar ratio of BA/Zr(O n Bu) 4 was 4.6:1. The viscosity of the precursor was very low (<8 mPa s) without the addition of solvents. Zirconium carbide powders were fabricated by the pyrolysis at 800 °C in argon and subsequent heating at various temperatures in vacuum for carbothermal reduction reaction. The pyrolysis behavior, phase composition and transformation, and microstructure of the as-fabricated ZrC powders were analyzed. The gases of CH 4 , CO and CO 2 released due to decomposition and evaporation of the organic component and transformation from ZrO 2 to ZrC during pyrolysis resulted in total 60–70% mass loss. The average grain size of the synthesized X-ray pure ZrC powders was less than 30 nm. Meanwhile, the pyrolysis mechanism of nano zirconium carbide powder was deduced.

Synthesis of Bis (Benzoyl Acetone Ethylene Diimine) Schiff Base Complex of Nickel (II) Supported on Magnetite Silica Nanoparticles (Fe3O4@SiO2/Schiff-Base of Ni(II)) and Using It as an Efficient Catalyst for Green Synthesis of 1-Amidoalkyl-2-Naphthols

Synthesis of Bis (Benzoyl Acetone Ethylene Diimine) Schiff Base Complex of Nickel (II) Supported on Magnetite Silica Nanoparticles (Fe3O4@SiO2/Schiff-Base of Ni(II)) and Using It as an Efficient Catalyst for Green Synthesis of 1-Amidoalkyl-2-Naphthols

Synthesis, characterization, and spectroscopic properties of new azo dyes derived from Sulfamerazine based on β- diketones and azo-metal (II) complexes

In the present study, two new azo dyes from 4-amino-N-(4-methyl-2- pyrimidinyl(benzenesulfonamide) with acetylacetone( L1) and benzoyl acetone(L2) were synthesized. The characterization of dyes has been described by IR,C.H.N,1H-NMR, and TGA. The reaction of these new dyes with acetate salts of copper(II) and nickel(II) in molar ratios of 1:2 was carried out to produce azo metal(II) complexes. Theanalytical data show that the metal to ligand ratio [M:L] in all complexes is (1:2). The spectral and analytical data revealed that this ligand behaves as a bidentate chelating. The thermal behavior of these compounds was investigated based on thermogravimetric (TGA) analyse. Thermal decomposition of these compounds is multi-stage processes.

Effects of the number of benzene rings on the properties of single-source ZrC-based liquid precursors and nano zirconium carbide powders thereof

Effects of carbon source in single-source ZrC-based liquid precursors on the properties of the precursors and precursor-derived nano ZrC powders were investigated. The liquid precursors were prepared by directly blending and heating zirconium n-butoxide with either 2,4-pentanedione, benzoyl acetone or 1,3-diphenyl-1,3-propanedione additives which have the same chemical composition and structure except for the number of benzene rings (0, 1 and 2, respectively) in order to control the carbon content in the precursors. The ceramic yield of the precursor decreased as the number of benzene rings in the precursors increased. The stability of the precursors in air and the carbon content of the ceramic powder increased when using 1,3-diphenyl-1,3-propanedione additive. X-ray pure nano zirconium carbide powders with ultra-fine size (30 nm), isotropic shape and homogeneous particle size distribution were synthesized from the liquid precursors containing two benzene rings in the structure. Compared with ZrC powders derived from the precursors containing zero or one benzene ring, the powder from the precursor containing two benzene rings was finer and more homogeneous in size distribution.

Synthesis of di- and poly-substituted phenols via [4 + 2] type cyclo-condensation

A new [4 + 2] type cyclocondensation was developed to prepare 3,5- and poly-substituted phenols using aryl ketoesters and ynones as the starting materials; Various substrates, such as aryl-, heteroaryl ketoesters and aryl-, vinyl-, alkyl substituted ynones, were employed. In addition, extending the substrate scope to benzoyl acetone provided 3,4,5-trisubstituted phenols.

Facile synthesis and characterization of macromolecular Eu(III) complexes with β-diketone ligands and poly(4-vinyl pyridine-co-methyl methacrylate)

Poly(4-vinyl pyridine-co-methyl methacrylate), PVM, was synthesized by radical copolymerization of 4-vinyl pyridine with methyl methacrylate. Afterward, the macromolecular Eu(III) complexes of general formula [Eu(β-diketonate)3(PVM)(H2O)], where β-diketonate = benzoylacetonate (BA), 1; dibenzoylmethanate (DBM), 2; thenoyltrifluoroacetonate (TTA), 3, were prepared and fully characterized by means of element analysis, thermal analysis, SEM, 1H NMR, 13C NMR, FT-IR, and UV-vis spectra. The macromolecular complexes can dissolve in many ordinary organic solvents (e.g. dimethylformamide, dimethylsulfoxide, and tetrahydrofuran), as well as emit strong red luminescence under ultraviolet light excitation. The room-temperature 5D0 lifetime and fluorescence quantum yield of 3 are 391 μs and 37%, respectively, which are far more than those of 1 (194 μs, 16%), 2 (160 μs, 18%), and Eu(TTA)3(H2O)2 (224 μs, 22%). The CIE coordinates of 1–3 are calculated as (0.49, 0.33), (0.62, 0.33) and (0.65, 0.34), respectively, demonstrating the promising utilization future of these complexes, especially the latter two, as luminescent functional materials used in large-area optical display.

Nickel(II) Phosphane‐ and N‐heterocyclic Carbene Complexes with Tridentate, Dianionic [S,N,O]2– Ligands

Square‐planar dinuclear nickel(II) complexes containing [S,N,O]2– ligands formed by condensation of acetyl acetone or benzoyl acetone with cysteamine were prepared. These dimeric nickel(II) compounds undergo bridge‐cleavage reactions with the cage phosphine PTA (PTA = 1,3,5‐triaza‐7‐phosphaadamantane) or in situ generated N‐heterocyclic carbenes. The resulting diamagnetic, square planar NiII complexes were characterized by spectroscopic methods and X‐ray diffraction.

Emulsion Stability Tes and Effect of HNO3 Concentration in the Internal Phase on Cadmium Ion Extraction using Liquid Membrane Emulsion Technique

Study on the emulsion stability and cadmium ion extraction tests was performed using the liquid membrane emulsion technique. This study aimed to determine the emulsion stability between the membrane phase and the internal phase with the variation of the ratio (2:1, 1:1, 2:3, and 1:2), and to determine the maximum conditions of cadmium ion extraction in a solution including the various concentration of HNO3 solution 1, 1.5, 2, and 2.5 M. This study is a laboratory experimental method using benzoyl acetone compound as cation carrier, kerosene as membrane phase, HNO3 solution as the internal phase, span-20 and span-80 as surfactants, and cadmium solution as the sample solution. Cadmium ion concentration in the external phase was determined by UV-VIS spectrophotometer. The result showed that the emulsion stability test which produced the most stable emulsion was in the ratio of the membrane phase and the internal phase 1:1. In addition, the concentration of the HN03 solution resulted in a maximum extraction percentage of 1.5 M with an extraction percentage was 95.28%.

Effect of Copper(II) and Cadmium(II) Ions Against the Percent Mercury Ion Extraction Using Emulsion Liquid Membrane Technique

The effect of copper(II) and cadmium(II) ions on the percent of mercury ion extraction using an emulsion liquid membrane technique have been performed. This study used HNO3 as an internal phase, mixed span 80 and span 20 as a surfactant, benzoyl acetone as cation carrier, kerosene as membrane phase, and mercury solution as a sample solution. Variations of concentrations of copper(II) and cadmium(II) ions added were 10, 20, and 30 ppm with mercury concentrations of 30 ppm. The result of the research showed that the addition of copper(II) ion with concentrations of 10 to 30 ppm decreased the percentage of mercury ion extraction 30 ppm by 12.12% and the addition of cadmium(II) ion with the concentration of 10 to 30 ppm decreased the percentage of mercury ion extraction 30 ppm by 11.74%.