- SELECTIVE OXIDATION OF ANTHRACENE TO ANTHRAQUINONE IN ACETIC ACID WITH AIR IN PRESENCE OF NITRIC ACID
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The oxidation of anthracene in acetic acid with air in the presence of small proportion of nitric acid produced high quality anthraquinone with acceptable yields.A possible mechanism is suggested which explains the predominance of the oxidation reaction compared with that of nitration.
- a Dolores,Aldrados, Luis F.,Burillo, Jose C.,Tijero, Julio F.
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- Reaction of Polycylic Aromatic Hydrocarbons (PAH) with Nitrogen Dioxide in Solution. Support for an Electron-Transfer Mechanism of Aromatic Nitration Based on Correlations Using Simple Molecular Orbital Theory
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Eight unsubstituted, polycyclic aromatic hydrocarbons (PAH) were allowed to react with nitrogen dioxide in dichlormethane at 25 deg C, and relative rate constants were obtained by direct competition techniques.The rate constants depend markedly on substrate structure, with over a 104 difference in rate constants between the least reactive (benzene) and most reactive (perylene) compounds studied.The major products formed from most substrates are nitroaromatics.Anthracene, however, also reacts with nitrogen dioxide to form appreciable amounts of 9,10-anthraquinone.Linear free energy relationships were determined between rate data and molecular orbital parameters based on models involving rate-determining ?-complex formation or electron-transfer (ET) reactions.Based on the better correlations obtained using the latter model, it is suggested that the more easily ionized PAH undergo nitration by an ET mechanism.Values of absolute rate constants for the nitration of three of the PAH (as measured by stopped-flow) also are reported and correlate well with our relative rate constants.The formation of 9,10-anthraquinone is suggested to result from the trapping of the intermediate anthracene radical-cation by water.
- Pryor, William A.,Gleicher, Gerald J.,Cosgrove, John P.,Church, Daniel F.
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- Tetranitroethylene. In Situ Formation and Diels-Alder Reactions
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The reaction of hexanitroethane with dienes gave the Diels-Alder adducts of tetranitroethylene.Thus, the reaction in refluxing benzene of hexanitroethane with anthracene gave 11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene.Similarly, 9-methylanthracene and 9,10-dimethylanthracene gave 9-methyl-11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene and 9,10-dimethyl-11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene, respectively.Cyclopentadiene reacted with hexanitroethane in methylene chloride at -10 deg C to give 5,5,6,6-tetranitro-2-norbornene.Reaction of the anthracene adduct of tetranitroethylene with sodium iodide gave the sodium salt of 12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one, which was protonated with acetic acid to give the corresponding nitro ketone.Treatment of the sodium salt with clorine and bromine gave 12-chloro-12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one and 12-bromo-12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one, respectively.
- Griffin, T. Scott,Baum, Kurt
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- Novel aromatic-polyamine conjugates as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase
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Three types of aromatic-polyamine conjugates (6a-6s) were designed, synthesized and evaluated as potential inhibitors for cholinesterases (ChEs). The results showed that anthraquinone-polyamine conjugates (AQPCs) exhibited the most potent acetylcholinesterase (AChE) inhibitory activity with IC 50 values from 1.50 to 11.13 μM. Anthracene-polyamine conjugates (APCs) showed a surprising selectivity (from 76- to 3125-fold) and were most potent at inhibiting butyrylcholinesterase (BChE), with IC50 values from 0.016 to 0.657 μM. A Lineweaver-Burk plot and molecular modeling studies indicated that the representative compounds, 6l and 6k, targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of ChEs. Furthermore, APCs did not affect HepG2 cell viability at the concentration of 100 μM. Consequently, these polyamine conjugates could be thoroughly and systematically studied for the treatment of AD.
- Hong, Chen,Luo, Wen,Yao, Dong,Su, Ya-Bin,Zhang, Xin,Tian, Run-Guo,Wang, Chao-Jie
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- NITRATION
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The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.
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Page/Page column 36; 46; 40; 57
(2020/05/28)
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- 2-Methyl-1,3-disulfoimidazolium polyoxometalate hybrid catalytic systems as equivalent safer alternatives to concentrated sulfuric acid in nitration of aromatic compounds
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Ionic liquid-derived polyoxometalate salts [mdsim]3[PM12O40] (where M?=?W and Mo) of two heteropolyacids H3PW12O40.nH2O and H3PMo12O40.nH2O were synthesized using 2-methyl-1,3-disulfoimidazolium chloride ([mdsim][Cl]) ionic liquid and the corresponding heteropolyacids. Three equivalents of [mdsim][Cl] were treated with the respective Keggin-structured heteropolyacids (one equivalent) in aqueous medium at room temperature to afford the water-stable ionic polyoxometalates as acidic solids. They were completely characterized using spectroscopic and other analytical techniques including thermal analysis and Hammett acidity studies. The inherent Br?nsted acidic properties of ─SO3H group of these polyoxometalate salts were studied for the nitration of aromatic compounds with 69% HNO3 at normal temperature and 80°C without use of any external concentrated sulfuric acid. These strongly acidic polyoxometalates display good recyclability and efficient reusability.
- Saikia, Susmita,Borah, Ruli
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- Nitration of arenes by 1-sulfopyridinium nitrate as an ionic liquid and reagent by in situ generation of NO2
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1-Sulfopyridinium nitrate was synthesized as a potent nitrating agent for the nitration of arenes without the need for any co-catalysts. A variety of nitro compounds were synthesized and fully characterized by IR, 1H NMR, 13C NMR, thermal gravimetric analysis (TGA), differential thermal gravimetry (DTG), CHN analysis and mass spectroscopy. Mechanistically, in situ generated nitrogen dioxide as a radical from the reagent is proposed for the presented nitration protocol.
- Moosavi-Zare, Ahmad Reza,Zolfigol, Mohammad Ali,Zarei, Mahmoud,Noroozizadeh, Ehsan,Beyzavi, M. Hassan
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p. 89572 - 89577
(2016/10/03)
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- Synthesis of new chiral 1,3-aminoalcohols derived from levoglucosenone and their application in asymmetric alkylations
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We have developed a simple procedure for the preparation of chiral 1,3-aminoalcohols using the biomass derivative levoglucosenone, as the chiral starting material. 1,3-aminoalcohols, bearing primary and tertiary amino groups, were tested as chiral catalysts in the asymmetric addition of diethyl zinc to benzaldehyde.
- Zanardi, María M.,Suárez, Alejandra G.
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supporting information
p. 3762 - 3765
(2015/06/08)
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- Phosphoric acid modified montmorillonite clay: A new heterogeneous catalyst for nitration of arenes
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The easily available montmorillonite clay is treated with phosphoric acid and 10 wt.% is found to be the optimum concentration of phosphoric acid that can be adsorbed chemically on the surface of the clay. Acidity of this phosphoric acid treated montmorillonite clay (PAM) is determined by volumetric as well as potentiometric titration and characterized. Catalytic efficacy of PAM in nitration of various aromatic compounds is reported.
- Bharadwaj, Saitanya K.,Boruah, Purna K.,Gogoi, Pradip K.
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p. 124 - 128
(2014/12/11)
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- Design of ionic liquid 3-methyl-1-sulfonic acid imidazolium nitrate as reagent for the nitration of aromatic compounds by in situ generation of NO 2 in acidic media
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3-Methyl-1-sulfonic acid imidazolium nitrate ([Msim]NO3) as a new Bronsted acidic ionic liquid and nitrating agent was prepared and used for the efficient nitration of aromatic compounds (even aniline derivatives). The dramatic effect of this reagent by in situ generation of nitrogen dioxide as a radical on aromatic compounds to give nitroarenes has been studied.
- Zolfigol, Mohammad A.,Khazaei, Ardeshir,Moosavi-Zare, Ahmad R.,Zare, Abdolkarim,Kruger, Hendrik G.,Asgari, Zhila,Khakyzadeh, Vahid,Kazem-Rostami, Masoud
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experimental part
p. 3640 - 3645
(2012/06/15)
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- Nitration of aromatic compounds under neutral conditions using the Ph 2PCl/I2/AgNO3 reagent system
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Aromatic compounds were nitrated efficiently under essentially neutral conditions by employing Ph2PCl in the presence of I2 and AgNO3. This method minimizes waste products compared to traditional methods and gives the corresponding mononitro derivatives in good to excellent yields in dichloromethane at room temperature.
- Nowrouzi, Najmeh,Zareh Jonaghani, Mohammad
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experimental part
p. 5081 - 5082
(2011/10/09)
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- Highly enantioselective synthesis of tetrahydroquinolines via cobalt(II)-catalyzed tandem 1,5-hydride transfer/cyclization
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A chiral catalyst prepared from N,N′-dioxide and Co(BF 4)2·6H2O was applied in the asymmetric hydride transfer initiated cyclization reaction, giving optically active tetrahydroquinolines in good yields with high enantioselectivities under mild reaction conditions. Meanwhile, in light of the absolute configuration of the product, a possible working model was proposed to explain the origin of the activation and asymmetric induction.
- Cao, Weidi,Liu, Xiaohua,Wang, Wentao,Lin, Lili,Feng, Xiaoming
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supporting information; scheme or table
p. 600 - 603
(2011/04/15)
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- Fast and efficient nitration of salicylic acid and some other aromatic compounds over H3PO4/TiO2-ZrO2 using nitric acid
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TiO2-ZrO2 (1/1)-surf with Ti and Zr molar ratio of 1/1 was prepared with surfactant through a sol-gel method. The optimum experimental condition was investigated for nitration of salicylic acid. Then, a number of nitration reactions were carried out with a variety of aromatic compounds in the optimum condition. The 25 wt% H3PO4/TiO2-ZrO2 (1/1)-surf catalyst showed good selectivity and yield in a short time for the nitration of salicylic acid and some other aromatic compounds.
- Kalbasi, Roozbeh Javad,Massah, Ahmad Reza,Zamani, Farzad,Hamid, Javaherian Naghash
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experimental part
p. 397 - 403
(2010/10/20)
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- A modular synthesis of highly substituted imidazolium salts
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A versatile and modular one-pot method for the preparation of differently substituted symmetrical and unsymmetrical imidazolium salts is reported, and 19 examples are given. In the key step, readily available formamidines and α-halo ketones are coupled to give imidazolinium salts 3, followed by imidazolium salt formation by acylation-induced elimination. For many substitution patterns of the imidazolium salt products, this efficient strategy compares favorably with well-known processes in terms of yield, ease of synthesis, and robustness.
- Hirano, Keiichi,Urban, Slawomir,Wang, Congyang,Glorius, Frank
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supporting information; experimental part
p. 1019 - 1022
(2009/07/18)
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- Asymmetric control in Diels-Alder cycloadditions of chiral 9-aminoanthracenes by relay of stereochemical information
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Two approaches to the synthesis of chiral 9-amino anthracenes are described. The first, by nucleophilic addition of organolithium reagents to imines promoted by BF3·OEt2, unexpectedly provided stable aminoboranes as products. The second approach, using palladium catalysed cross coupling, was more successful for primary amines, and the key 9-(α-methylbenzylamino)anthracene subjected to cycloadditions with N-methyl maleimide and maleic anhydride. Excellent reactivity was achieved with good levels of diastereoselectivity, through a favourable combination of electrostatic and hydrogen bonding effects. Trial studies of the retro Diels-Alder reaction of these cycloadducts were also performed.
- Adams, Harry,Bawa, Ramadan A.,McMillan, Keith G.,Jones, Simon
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p. 1003 - 1012
(2008/02/03)
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- Ammonium nickel sulphate mediated nitration of aromatic compounds with nitric acid
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Aromatic compounds were efficiently nitrated under mild conditions employing ammonium nickel sulphate and nitric acid as a reagent. This procedure works efficiently at room temperature yielding mononitro derivative in fair to good yield with high regioselectivity.
- Tasneem,Ali,Rajanna,Saiparakash
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p. 1123 - 1127
(2007/10/03)
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- Nitration of polycyclic aromatic hydrocarbons using a supported catalyst
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We report the use of a catalyst, sulfuric acid supported on silica-gel, as a promising method for facile, high yielding, regioselective syntheses of mononitrated polycyclic aromatic hydrocarbons, 6-nitrochrysene, 1- nitropyrene, 1-nitronaphthalene, 2-nitrofluorene, 3-nitrofluoranthene, and 9- nitroanthracene.
- Smith, Amy C.,Narvaez, Lorena D.,Akins, Bridget G.,Langford, Moses M.,Gary, Thomas,Geisler, Victoria J.,Khan, Farooq A.
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p. 4187 - 4192
(2007/10/03)
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- Solvation effects on the rate of protolytic cleavage of a 9-nitroanthracene meisenheimer σ complex
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The kinetics of protolytic cleavage of the Meisenheimer σ complex of 9-nitroanthracene with methoxide ion in alcohols and their mixtures with DMSO were studied by spectrophotometry. The reaction rate increases with decreasing inductive and increasing steric constants of the alkyl radicals in the alcohols. In DMSO-alcohol mixtures, the effect of σconstants is the opposite, which is explained by formation of poorly active heteroassociates between the aprotic and protic molecules.
- Blokhin
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p. 1793 - 1795
(2007/10/03)
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- Abnormal orientation in nitration of anthracene, pyrene, and perylene with pyridinium nitrate. 2-Nitroanthracene and 4-nitropyrene
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Nitration by undissociated nitric acid which presumably forms at thermolysis (115°C) of pyridinium nitrate in pyridine selectively proceeds with respect to aromatic substrates and nonselectively with respect to various positions in aromatic rings. Whereas in electrophilic nitration forms a single isomer of mononitro products, the process under study yields two mononitro isomers, and nitration occurs only with polycyclic hydrocarbons containing a butadiene fragment included into neighboring rings (anthracene, naphthacene, pyrene, and perylene). On the contrary, benzene and its derivatives, naphthalene, phenanthrene, and triphenylene are not nitrated. Beside pyridinium nitrate as nitrating agents giving two isomeric mononitro arenes from polycyclic compounds are used tetranitromethane in pyridine and ammonium nitrate in a mixture pyridine-acetic anhydride. The side products of the reaction are biaryls, quinones (in particular, with unusually located carbonyl groups), and dyes containing aci-nitro and oxo groups.
- Nefedov
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p. 1165 - 1171
(2007/10/03)
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- Electron Affinities of Naphthalene, Anthracene and Substituted Naphthalenes and Anthracenes
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The determination of electron transfer equilibria A(1-) + B = A + B(1-) in the gas phase, with a pulsed-electron high-pressure mass spectrometer, leads to ΔG10, ΔH10, and ΔS10 values.These can be converted into the free energy, enthalpy and entropy changes, ΔGa0(B), ΔHa0(B) and ΔSa0(B), for the reaction e + B = B(1-), since the corresponding values for the reference compounds A are known.Results were obtained for 18 substituted naphthalenes, anthracene and substituted anthracenes.The results are compared with some theoretical predictions and the corresponding reduction potentials in solution.Rate constants for 13 exoergic electron-transfer reactions were also measured.These were found to be close to the ADO collision rates.
- Heinis, Thomas,Chowdhury, Swapan,Kebarle, Paul
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p. 358 - 365
(2007/10/02)
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- On the Reaction between Anthracene and the Nitrosonium Ion. A Simple Method for the Preparation of 9,10-Anthraquinone and Some Comments on its Formation in Aromatic Nitration
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A summary of the possible electron-transfer reactions between anthracene and the nitrosonium ion, and a convenient and simple method for the synthesis of 9,10-anthraquinone from anthracene, NaNO2 and CH3OH in CH2Cl2/CF3COOH are presented.The suggestion that the formation of 9,10-anthraquinone in the N2O4 nitration of anthracene originates from trapping of the anthracene radical cation by water is demonstrated to be invalid, e.g., by experiments involving H218O.Instead, 9,10-anthraquinone is suggested to be formed in the N2O4-based and in other related systems via foll ow-up reactions to an initial 1,4-addition across the 9,10 positions of anthracene.
- Radner, Finn
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- ELECTROCHEMICALLY INITIATED FRAGMENTATION REACTION OF 9,9'-DINITRO-9,9',10,10'-TETRAHYDRO-10,10'-BIANTHRYL
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A mechanism for the electroreduction of 9,9'-dinitro-9,9',10,10'-tetrahydro-10,10'-bianthryl in DMF, which results in the formation of anthracene and 9-nitroanthracene has been proposed on the basis of data from polarography, cyclic voltammetry, and electrolysis at a controlled potential.
- Mendkovich, A. S.,Mikhal'chenko, L. V.,Gul'tyai, V. P.
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p. 1163 - 1166
(2007/10/02)
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- The Reaction of Anthracene with Nitrogen Dioxide Revisited
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The primary products of the reaction of anthracene (AN) with nitrogen dioxide are cis- and trans-9,10-dinitro-9,10-dihydroanthracene, identified by NMR and single-crystal X-ray analysis.The chemical literature contains conflicting product analyses for this reaction, and the discrepancies are rationalized in terms of the thermal and chemical lability of these primary products.These products are rationalized in terms of a radical reaction of AN with NO2, rather than an electrophilic reaction mechanism.Analysis of the reaction kinetics reveal the formation of an intermediate, apparently of the charge-transfer type, between AN and one molecule of nitrogen dioxide.This intermediate precedes the formation of the 9-nitro-9,10-dihydroanthryl radical that readily couples with a molecule of nitrogen dioxide to yield cis- and trans-9,10-dihydroanthracene in a 1:1 ratio.
- Squadrito, Giuseppe L.,Fronczek, Frank R.,Watkins, Steven F.,Church, Daniel F.,Pryor, William A.
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p. 4322 - 4326
(2007/10/02)
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- Electrolysis at an Anthracene Crystal/Aqueous NO3- Solution Interface: The Role of Crystal Defects
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The electrolysis of a 1 M solution of NaNO3 by means of an anthracene crystal electrode results in the production of many surface reaction products, including 9-nitroanthracene (9NA), bianthronyl (BA), and anthraquinone (AQ).The production of 9NA and BA have been shown to depend on the square of the current density.This dependence was rationalized by hypothesizing the need for the simultaneous discharge of two carriers at adjoining lattice defect sites.By annealing the crystals, it was found that the efficiency of producing 9NA was reduced by a factor of as much as 6; this supports the hypothesis.
- Pope, M.,Mao, B.,Steigman, J.,Geacintov, N. E.
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p. 1719 - 1720
(2007/10/02)
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- Oxidative Aromatic Nitration with Charge-Transfer Complexes of Arenes and Nitrosonium Salts
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Brightly colored solutions are obtained immediately upon the exposure of various arenes (ArH) to nitrosonium (NO+) salts.The colors arise from the charge-transfer transitions of 1:1 complexes +> that are reversibly formed as persistent intermediates.However the yellow-red charge-transfer (CT) colors are readily bleached by dioxygen, and the corresponding nitroarenes (ArNO2) can be isolated in excellent yields from acetonitrile solutions.Such an oxidative aromatic nitration of aromatic donors proceeds via the initial autooxidation of the charge-transfer complex.The collapse of the resulting radical ion pair .+,NO2> to the ?-adduct, followed by the loss of proton, affords ArNO2.Direct evidence for electron transfer in the initial step when anthracene is treated with NO+PF6- stems for the isolation of (a) the anthracene ion radical salt .+PF6-> along with nitric oxide in dichloromethane solution and (b) the formation of 9-nitroanthracene (admixed with anthraquinone) in the more polar acetonitrile.The aromatic products (and isomer distribution) from oxidative aromatic nitration are highly reminiscent of those from electrophilic aromatic nitration.The possibility of common reactive intermediates in these two distinctive pathways for aromatic nitration is discussed.
- Kim, E. K.,Kochi, J. K.
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p. 1692 - 1702
(2007/10/02)
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- Electron Transfer Activation in the Thermal and Photochemical Osmylation of Aromatic EDA Complexes with Osmium(VIII) Tetroxide
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Various types of arenes (Ar) spontaneously form with osmium tetroxide a series of highly colored solutions of electron donor-acceptor or EDA complexes such as in nonpolar solvents.Charge-transfer or CT osmylation is simply effected by the actinic irradiation of the absorption bands (hνCT), and the molecular structures of the OsO4 adducts of benzene (B) and anthracene (A) are elucidated by X-ray crystallography.The metastable ion pair is established as the seminal intermediate in CT osmylation by time-resolved picosecond spectroscopy attendant upon the specific excitation of the EDA complex.According to Scheme II, the rapid collapse of the ion pair (eq 16) with a rate constant k ca. 1E9 s-1 represents the critical transformation in adduct formation.Importantly, this ion-pair mechanism accomodates (a) the osmylation of a wide range of arene donors from the mononuclear benzenes to the electron-rich polycyclic arenes (Table V) under the common umbrella of photoexcitation and (b) the profound effect on the regiochemistry of anthracene (Table VI) by subtle variations in solvent polarity.In the absence of deliberate irradiation (i.e., in the dark), the EDA complexes of OsO4 with electron-rich arenes, especially the polynuclear naphthalene, anthracene and phenanthrene, slowly undergo the direct thermal or DT osmylation to yield the same series of adducts.As such, there is a close relationship between the photoexcited state leading to CT osmylation and the activated complex in DT osmylation.Indeed the formation of the highly unusual adduct A by OsO4 addition to the terminal ring of anthracene binds in common the transition state for DT osmylation and the ion-pair collapse in CT osmylation.Thus the electron-transfer mechanism in Scheme IV employs the adiabatic ion pair (eq 20) to account for the same regiospecificities in DT osmylations.Such a unified view of arene osmylation can be extended to the promoted thermal or PT osmylation via the five-coordinate OsO4(py), as a commonly practiced for bis-hydroxylation of alkenes.
- Wallis, J. M.,Kochi, J. K.
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p. 8207 - 8223
(2007/10/02)
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- ELECTROCHEMISTRY AT ANTHRACENE CRYSTAL/AQUEOUS NO2-, NO3- SOLUTION INTERFACE
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Holes (radical cations) were injected into one face of an anthracene crystal slab and discharged at the other face, which was in contact with a neutral aqueous solution containing 1 M NO3- or NO2-.Hole current densities (J) of up to 700 μAcm-2 generated a variety of surface oxidation products including anthraquinone, 9-nitroanthracene (9NA), oxanthrone, anthrone, bianthronyl (BA), and 9,10-dinitroanthracene with both NO3- and NO2- solutions.The amount of BA and 9NA increased as J2.With increasing NO3- concentration, the amount of 9NA produced increased, while that of BA decreased.It was concluded that 9NA is made by cooperation of two holes on adjoining molecules at defect sites.
- Leong, Baldwin,Pope, Martin,Steigman, Joseph
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p. 2506 - 2511
(2007/10/02)
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- Nitration of Polycyclic Aromatic Hydrocarbons by Dinitrogen Tetraoxide. II. Synthetic and Mechanistic Aspects
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Treatment of polycyclic aromatic hydrocarbons by dinitrogen tetraoxide in dichloromethane solution leads to the clean production of mononitro derivatives with high positional selectivity in almost quantitative yields.For substrates less reactive than chrysene the addition of catalytic amounts of acid is required for the reaction to proceed at convenient rates.Being very easily performed, the method should be regarded as the best yet found for the synthesis of small amount of these, in many cases, mutagenic mononitro compounds.From studies on relative reactivities, isomer distributions, and the effect of acid, base and nitrosonium ion on the reaction, a mechanism involving initial attack of a novel electrophile, nitrosated dinitrogen tetraoxide, is proposed.The initially formed ?-complex is suggested to be transformed into the nitro ?-complex via a pathway involving radical pairs, thus explaining the observation by others of CIDNP effects on the reaction path of nitrous acid catalyzed nitration, a reaction proposed to follow the same reaction scheme.
- Eberson, Lennart,Radner, Finn
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p. 343 - 356
(2007/10/02)
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