84-65-1Relevant articles and documents
Alcohol oxidation and aldol condensation during base-catalyzed reaction of primary alcohols with 1-chloroanthraquinone
Shabany,Abel,Evans,McRobbie,Gokel
, p. 6705 - 6708 (2000)
When chloroanthraquinone is treated with primary alcohols under basic conditions, the notoriously low yields observed for substitution result in part from oxidation of the alcohol followed by aldol condensation. (C) 2000 Elsevier Science Ltd.
Electron Paramagnetic Resonance, ENDOR and TRIPLE Resonance of some 9,10-Anthraquinol Radicals in Solution
Maekelae, Reijo,Vuolle, Mikko
, p. 3257 - 3260 (1990)
EPR, ENDOR and TRIPLE resonance spectra are recorded for 9,10-anthraquinol-1-sodium sulphonate, 9,10-anthraquinol-2-sodium sulphonate, 9,10-anthraquinol-1,5-disodium sulphonate and 9,10-anthraquinol-2,6-disodium sulphonate cation radicals.The splittings of the 9,10-anthraquinol cation radical have been assigned by deuteration.The spectra of the deuterated anthraquinol cation radicals and the assignment of hyperfine coupling constants are discussed.
Kinetics and mechanism of anthracene oxidation with tert-butyl hydroperoxide over metal-organic frameworks Cr-MIL-101 and Cr-MIL-100
Ivanchikova,Skobelev,Kholdeeva
, p. 175 - 181 (2015)
The oxidation of anthracene (AN) with tert-butyl hydroperoxide (TBHP) over metal-organic frameworks (MOFs) Cr-MIL-101 and Cr-MIL-100 produced anthraquinone (AQ) in a nearly quantitative (>99%) yield after 1 and 4 h, respectively, at 100 °C in chlorobenzene (ClPh). At initial stages of the reaction, some amounts (a was found to be similar for MIL-101 and MIL-100 (15 kcal/mol) while pre-exponential factors were different (7·106 and 3·106 L/(mol·min), respectively). The kinetic results indicated that the AN oxidation with TBHP over both MIL-101 and MIL-100 is not controlled by diffusion. No adsorption of AN on the MOFs from ClPh solution was found at the reaction temperature. A mechanism that involves a reversible interaction between TBHP and CrIII centers within the MOF framework producing an active oxidizing species (rate-limiting step), followed by oxygen atom transfer from the peroxo species to the aromatic substrate to give primary oxygenated product(s), further oxidation of which leads to AQ, has been suggested.
Oxidation with the H2O2-VO3--pyrazine-2-carboxylic acid reagent 2. Oxidation of alcohols and aromatic hydrocarbons
Shul'pin, G. B.,Druzhinina, A. N.,Nizova, G. V.
, p. 1326 - 1329 (1993)
Aromatic hydrocarbons are oxidized with hydrogen peroxide in the presence of catalytic amounts of VO3- and pyrazine-2-carboxylic acid into phenols (provided excess hydrocarbon is used) or into quinones (at high H2O2 concentrations). 2-Propanol, ethanol, cyclohexanol, and benzyl alcohol are transformed into the corresponding aldehydes and ketones under the same conditions (without a solvent or in MeCN). - Key words: oxidation, hydrogen peroxide, vanadium complexes; aromatic hydrocarbons; alcohols.
Pulse Radiolyses of Anthraquinone and Anthraquinone-Triethylamine in Acetonitrile and Toluene at Room Temperature
Nakayama, Toshihiro,Ushida, Kiminori,Hamanoue, Kumao,Washio, Masakazu,Tagawa, Seiichi,Tabata, Yoneho
, p. 95 - 104 (1990)
Nanosecond pulse radiolysis of anthraquinone (AQ) in several solvents has been performed at room temperature, and the following results are obtained: (1) In acetonitrile (CH3CN), the formation of triplet AQ and a free-radical anion (AQ.-) of AQ is observed.The former is produced by energy transfer from an excited neutral of CH3CN which may be produced via the geminate recombination of a radical cation and a radical anion of CH3CN in a spur, while the latter is produced by electron transfer from anionic species such as a solvated electron, a monomeric and/or dimeric radical anion of CH3CN.In CH3CN-triethylamine (TEA), both free AQ.- and triplet AQ mentioned above are also produced; however, the latter reacts with TEA, giving rise to the formation of free AQ.- (from the second triplet state of AQ) and an exciplex of the lowest triplet state of AQ with ground-state TEA.This exciplex decomposes to free AQ.- and the radical cation of TEA. (2) In toluene, only triplet AQ is produced by energy transfer from triplet toluene to AQ, and, in the presence of TEA, the formation of the triplet exciplex of AQ-TEA is observed.On a microsecond timescale, however, this exciplex changes to a contact ion pair followed by proton transfer, generating anthrasemiquinone radical and triethylamine radical in accordance with the result of photolysis.
Photoproducts of carminic acid formed by a composite from Manihot dulcis waste
Antonio-Cisneros, Cynthia M.,Dvila-Jimnez, Martn M.,Elizalde-Gonzlez, Mara P.,Garca-Daz, Esmeralda
, p. 725 - 732 (2015)
Carbon-TiO2 composites were obtained from carbonised Manihot dulcis waste and TiO2 using glycerol as an additive and thermally treating the composites at 800 °C. Furthermore, carbon was obtained from manihot to study the adsorption,
INTRODUCTION OF ONE-CARBON UNITS DURING ANTHRAQUINONE-CATALYSED PULPING OF WOOD
Cameron, Donald W.,Samuel, Eva L.
, p. 1841 - 1842 (1981)
Anthraquinone- and tetrahydroanthraquinone-catalysed pulping of Pinus radiata has given 10-methyl-9-anthrone (2) and derivatives (3) and (4), introduction of the carbon substituent involving carbohydrate constituents of the wood.
Anthrone complexation with aliphatic amines in an aprotic medium
Serdyuk,Abakumov,Kapitanov,Kasianczuk,Opeida
, p. 1470 - 1473 (2013)
Aromatic ketone (anthrone) complexation with aliphatic amines is studied by UV-Vis, 1H, 1H-1H COSY NMR spectroscopy. It is found that the catalytic activity of aliphatic amine is observed in the reaction of anthrone oxidation by molecular oxygen in aprotic media due to the formation of intermolecular complexes consisting of two anthrone molecules and one aliphatic amine molecule.
The influence of the structure of aliphatic amine on its catalytic activity in the oxidation of anthrone in dimethyl sulfoxide
Serdyuk,Kasyanchuk,Opeida,Tolkunov
, p. 1094 - 1096 (2011)
The catalytic activity of several aliphatic amines in the liquid-phase oxidation of anthrone by molecular oxygen in dimethyl sulfoxide was studied. The kinetic data obtained were compared with the results of quantum-chemical calculations. The catalytic activity of aliphatic amines in the reaction under consideration was directly proportional to an increase in the absolute value of the heat of formation of the corresponding ammonium cation.
2,7-Dithia-, 2,8-Dithia-, and 2,9-Dithia(9,10)anthracenophanes. High Reactivity Induced by Aryl-Ring Deformation
Chung, Judy,Rosenfeld, Stuart M.
, p. 387 - 388 (1983)
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Matrix Isolation of 3,4-Benzocyclodeca-3,7,9-triene-1,5-diyne
Koetting, Carsten,Sander, Wolfram,Kammermeier, Stefan,Herges, Rainer
, p. 799 - 803 (1998)
3,4-Benzocyclodeca-3,7,9-triene-1,5-diyne (3) has been synthesized from two different precursors and characterized by means of matrix-isolation spectroscopy. Energies, structures and IR spectra of the product, the intermediate 9,10-didehydroanthracene (4), and of the transition state of the Bergman cyclization 3 → 4 have been calculated at the B3LYP/6-31G * level of theory.
Thermochromism at room temperature in overcrowded bistricyclic aromatic enes: Closely populated twisted and folded conformations
Levy, Amalia,Pogodin, Sergey,Cohen, Shmuel,Agranat, Israel
, p. 5198 - 5211 (2007)
The overcrowded thermochromic bistricyclic aromatic enes (BAEs) 10-(9′H-fluoren-9′-ylidene)-9(10H)-anthracenone (6), 10-(11′H-benzo[b]fluoren-11′-ylidene)-9(10H)-anthracenone (7), and 10-(1′,8′-diaza-9′H-fluoren-9′-ylidene)-9(10H) -anthracenone (8) were synthesized by applying Barton's two-fold extrusion diazo-thione coupling method and their crystal and molecular structures were determined. BAEs 6-8 exhibit thermochromic behavior at room temperature due to the equilibrium between the yellow anti-folded conformations and the thermochromic purple, blue, or red twisted conformations. The NMR experiments demonstrate a fast interconversion of the twisted and the anti-folded conformers of 6-8 in solution. BAE 7 readily undergoes E,Z-topomerization at room temperature with the coalescence point at 297 K and the relatively low energy barrier of ΔGc?(t⊥) = 65.5 kJ/mol. B3LYP/6-311++G(d,p) calculations predict anti-folded a-6 and a-7 to be less stable than twisted t-6 and t-7 by 0.8 and 1.3 kJ/mol, respectively, whereas a-8 is more stable than t-8 by 10.7 kJ/mol. DFT calculations of 6-8, 9-(9′H-fluoren-9′-ylidene)-9H-fluorene (1), [10′-oxo- 9′(10′H)-anthracenylidene]-9(10H)-anthracenone (2) and their 1,8-diaza-substituted derivatives show that substitution in the fluorenylidene unit destabilizes the twisted conformations by 11-22 kJ/mol, while introduction of nitrogen atoms at the 1 and 8 positions of anthracenylidene unit destabilizes the anti-folded conformations by 14-18 kJ/mol. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Quinaldinium Chlorochromate Supported on Alumina: A New and Efficient Reagent for the Oxidation of Alcohols
Degirmenbasi, Nebahat,Oezguen, Beytiye
, p. 1565 - 1569 (2003)
The new, mild chromium(VI) oxidizing agent, quinaldinium chlorochromate supported on neutral alumina, was prepared as a stable yellow solid. The reagent is suitable to oxidize various primary and secondary alcohols to the corresponding carbonyl compounds and anthracene to anthraquinone in good yields.
Kinetics of amine catalysed oxidation of anthrone by oxygen in aprotic solvents
Serdyuk,Kasianchuk,Opeida
, p. 391 - 394 (2010)
Catalytic activity for the series of aliphatic and aromatic amines in liquid-phase oxidation of anthrone with molecular oxygen was studied gas-volumetrically and spectroscopically. It was shown that the studied amines are arranged in the following order of decreasing catalytic activity: NH 3 > RNH2 > R1R2NH > R 1R2R3N > ArNR2. A kinetic scheme for the process is proposed. Pleiades Publishing, Ltd., 2010.
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Wheeler
, p. 949 (1958)
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Anthracene-based fluorescence turn-on chemodosimeter for the recognition of persulfate anion
Badekar, Pooja S.,Kumbhar, Anupa A.
, p. 3917 - 3923 (2018)
The anthracene thiosemicarbazone (ATSC) fluorescence 'turn-on' chemodosimeter for the detection of the persulfate anion (S2O82-) in 90% DMSO has been developed. ATSC is simple and exhibits high selectivity toward S2O82- anion in the presence of large interferences from other anions or cations. A fluorescence change from blue to green visualized under the UV light makes it possible to detect the persulfate anion with naked-eye. A mechanism underlying the molecular recognition has been explained from the 1H-NMR and single crystal X-ray structure experiments.
Perkin, A. G.
, p. 634 (1891)
Solid-state photolysis of anthracene-linked ammonium salts: The search for topochemical anthracene photodimerizations
Ihmels, Heiko,Leusser, Dirk,Pfeiffer, Matthias,Stalke, Dietmar
, p. 6867 - 6875 (2000)
The reaction of 9-N,N-dimethylaminomethylanthracene 1 with aromatic carboxylic acids gave crystalline salts (2a, 2b, 3a and 3b), which were irradiated in the solid state. Whereas salt 3a was selectively transformed to the dimer 4a, the other salts were ph
Anthryl-1,2,4-oxadiazole-substituted calix[4]arenes as highly selective fluorescent chemodosimeters for Fe3+
Chen, Ying-Jung,Yang, Shun-Chieh,Tsai, Chia-Chen,Chang, Kai-Chi,Chuang, Wen-Han,Chu, Wei-Lun,Kovalev, Vladimir,Chung, Wen-Sheng
, p. 1025 - 1034 (2015)
Fluorescent chemosensors 1 and 2, with 1,2,4-oxadiazoles as the binding ligands and anthracene as the fluorophore, were synthesized through sequential 1,3-dipolar cycloaddition reactions of 25,27-dioxyacetonitrilecalix[4]arenes 8 and 11. The fluorescence
Photolysis of an Amphiphilic Assembly by Calixarene-Induced Aggregation
Wang, Yi-Xuan,Zhang, Ying-Ming,Liu, Yu
, p. 4543 - 4549 (2015)
Photosensitizers generally show great tendency for self-aggregation in aqueous media, leading to quenched fluorescence and lower photosensitizing ability. Herein, we report that amphiphilic anthracene is highly photoreactive after aggregation induced by p-sulfonatocalix[4]arene in water. The formation of a host-guest supramolecular assembly and the photolysis of the anthryl core are identified by UV-vis and NMR spectroscopy, dynamic light scattering, and transmission electron microscopy. Additionally, the assembly exhibited efficient photolysis with visible light in the presence of exogenous photosensitizers. This approach could be extended to various photoresponsive self-assemblies and applications in phototherapy and the design of photodegradable materials. (Chemical Equation Presented)
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Gleason,Dougherty
, p. 310,311, 313 (1929)
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Reactivity of 9-anthracenecarboxylate in the presence of Mn(II) and Mn(III) ions: Biomimetic aerobic oxidative decarboxylation catalysed by a manganese(III) 2,2′-bipyridine complex
Albela, Belén,Bonneviot, Laurent,Corbella, Montserrat,Font-Bardia, Mercè,Garcia-Cirera, Beltzane,Turquet, Fran?ois-Xavier
, (2020)
The stability of the 9-anthracenecarboxylate (AnthCO2–) in the presence of manganese ions and 2,2′-bipyridine (bpy) was explored. Two Mn(II) species were isolated: a one-dimensional system [Mn(bpy)(AnthCO2)2]n (1) and a dinuclear [{Mn(bpy)(AnthCO2)}2(μ-OH2)(μ-AnthCO2)2] compound (2), which was characterized by X-ray diffraction. Compound 2 can be obtained by hydrolysis of 1. These compounds present a specific electron paramagnetic resonance (EPR) signature and weak antiferromagnetic coupling, which is slightly stronger for the dinuclear complex (?4.8 cm?1) than for the chain (?1.3 cm?1). In the presence of Mn(III) ions AnthCO2– is not stable for long time. From the Mn(III) solution obtained by a comproportionation reaction between Mn(II) and Mn(VII) salts, first, a tetranuclear [Mn4(μ-AnthCO2)6(μ-O)2(bpy)2(ClO4)2] compound was isolated, showing the antiferromagnetic properties typical of a butterfly [Mn4O2]8+ core (J1 = ?41.0 cm?1, J2 = ?8.4 cm?1, J3 = ?10.6 cm?1 and DMn = ?3.7 cm?1). After that, the solution became yellow due to the reduction of the Mn(III) complex to a Mn(II) complex, and the decarboxylation and oxidation of the AnthCO2– ligand. This oxidation can lead to different compounds, depending on the reaction conditions (temperature and amount of O2): an ester, derived from the AnthCO2– and the intermediate 10-hydroxyanthrone, and the 9,10-anthraquinone.
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Bowen,Nash
, (1928)
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Synthesis, structural elucidation, and catalytic activity of bimetallic rhenium-tin complexes containing Schiff base ligand
Kaur, Manpreet,Kapila, Akanksha,Yempally, Veeranna,Kaur, Harminder
, (2021/10/04)
Novel bimetallic systems with Re and Sn metals, containing Schiff base linker were designed and explored for their cooperative effect in the catalysis. ReSn bimetallic complexes were prepared by adopting a two-step synthesis procedure, which includes cova
Combining Structural with Functional Model Properties in Iron Synthetic Analogue Complexes for the Active Site in Rabbit Lipoxygenase
Bonck, Thorsten,De Waal Malefijt, Matina Elo?se,Dobbelaar, Emiel,Kelm, Harald,Klein, Johannes E. M. N.,Krüger, Hans-J?rg,Rauber, Christian,Schmitz, Markus
supporting information, p. 13145 - 13155 (2021/09/03)
Iron complexes that model the structural and functional properties of the active iron site in rabbit lipoxygenase are described. The ligand sphere of the mononuclear pseudo-octahedral cis-(carboxylato)(hydroxo)iron(III) complex, which is completed by a tetraazamacrocyclic ligand, reproduces the first coordination shell of the active site in the enzyme. In addition, two corresponding iron(II) complexes are presented that differ in the coordination of a water molecule. In their structural and electronic properties, both the (hydroxo)iron(III) and the (aqua)iron(II) complex reflect well the only two essential states found in the enzymatic mechanism of peroxidation of polyunsaturated fatty acids. Furthermore, the ferric complex is shown to undergo hydrogen atom abstraction reactions with O-H and C-H bonds of suitable substrates, and the bond dissociation free energy of the coordinated water ligand of the ferrous complex is determined to be 72.4 kcal·mol-1. Theoretical investigations of the reactivity support a concerted proton-coupled electron transfer mechanism in close analogy to the initial step in the enzymatic mechanism. The propensity of the (hydroxo)iron(III) complex to undergo H atom abstraction reactions is the basis for its catalytic function in the aerobic peroxidation of 2,4,6-tri(tert-butyl)phenol and its role as a radical initiator in the reaction of dihydroanthracene with oxygen.