Nitration and oxidation of anthraquinone dimethyl derivatives

Arient, J.; Podstata, J.

doi:10.1135/cccc19743117

Cited by 10 publications

(12 citation statements)

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“…The synthesis of 1 was achieved in two steps by adapting previous procedures described in the literature (Scheme S1). , Benzoquinone (3.25 g, 30 mmol), isoprene (10.0 mL), and traces of hydroquinone (two spatula tips), were suspended in 20.0 mL of absolute ethanol. The mixture was placed in a 40.0 mL autoclave and heated at 130 °C for 6 h. Once the autoclave reached room temperature, the mixture was dissolved in a potassium hydroxide solution in ethanol (8.5 g of KOH in 200 mL of EtOH) in a round-bottom flask.…”

Section: Methodsmentioning

confidence: 99%

“…A solution of 2,6-dimethyl-9,10-anthraquinone (1.0 g) in 12.0 mL of 25% nitric acid was placed in a 40.0 mL autoclave and heated at 220 °C for 3 h. After it cooled to room temperature, the yellow precipitate was filtered under vacuum and washed with water. The solid was dried overnight, affording pure 1 with 69% yield …”

Section: Methodsmentioning

confidence: 99%

“…The synthesis of 2 was achieved in two steps by adapting previous procedures described in the literature (Scheme S1). , First, a solution of 1,4-naphthoquinone (9.35 g, 0.059 mol) and 2,4-hexadiene (5.0 g, 0.605 mol) in toluene (35 mL) was heated at 65 °C for 4 d. Subsequently, the solvent was evaporated, and the remaining oily solid was used in the next step without further purification. The oily solid (15.0 g) was disolved in 250 mL of absolute ethanol and added to a solution of KOH (30 g) in ethanol (1.25 L), while cooled at 10 °C.…”

Section: Methodsmentioning

confidence: 99%

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Proton-Coupled Electron Transport in Anthraquinone-Based Zirconium Metal–Organic Frameworks

et al. 2017

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The ditopic ligands 2,6-dicarboxy-9,10-anthraquinone and 1,4-dicarboxy-9,10-anthraquinone were used to synthesize two new UiO-type metal-organic frameworks (MOFs; namely, 2,6-Zr-AQ-MOF and 1,4-Zr-AQ-MOF, respectively). The Pourbaix diagrams (E vs pH) of the MOFs and their ligands were constructed using cyclic voltammetry in aqueous buffered media. The MOFs exhibit chemical stability and undergo diverse electrochemical processes, where the number of electrons and protons transferred was tailored in a Nernstian manner by the pH of the media. Both the 2,6-Zr-AQ-MOF and its ligand reveal a similar electrochemical pK value (7.56 and 7.35, respectively) for the transition between a two-electron, two-proton transfer (at pH < pK) and a two-electron, one-proton transfer (at pH > pK). In contrast, the position of the quinone moiety with respect to the zirconium node, the effect of hydrogen bonding, and the amount of defects in 1,4-Zr-AQ-MOF lead to the transition from a two-electron, three-proton transfer to a two-electron, one-proton transfer. The pK of this framework (5.18) is analogous to one of the three electrochemical pK values displayed by its ligand (3.91, 5.46, and 8.80), which also showed intramolecular hydrogen bonding. The ability of the MOFs to tailor discrete numbers of protons and electrons suggests their application as charge carriers in electronic devices.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Proton-Coupled Electron Transport in Anthraquinone-Based Zirconium Metal–Organic Frameworks

et al. 2017

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“…Materials: 2,6-anthracenedicarboxylic acid (2,6-ADCA), 1,4-anthracenedicarboxylic acid (1,4-ADCA), and 9,10-anthracenedicarboxylic acid (9,10-ADCA) were synthesized following previously reported procedures with minimal modifications and characterized by 1H NMR spectroscopy (Figures S12-S14). [28][29][30][31][32] All other chemicals and solvents including anthracene (> 99 %), KOH (85 %), NH4OH (25-30%), acetic acid (reagent grade > 99%), dimethylformamide (HPLC grade > 99%), dimethylacetamide (spectrophotometric grade > 99%), tetrahydrofuran (ACS grade > 99 %), ethyl acetate (HPLC grade > 99.9%), acetone (HPLC grade > 99.5%), and butanone (ACS grade > 99%) were used as received without further purification from Alfa Aesar, Fisher Scientific, or Sigma-Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Systematic investigation of the excited-state properties of anthracene-dicarboxylic acids

Rowe

Hay

Maza

et al. 2017

Journal of Photochemistry and Photobiology A: Chemistry

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We report the photophysical properties of three anthracene-dicarboxylic acids -1,4-anthracene dicarboxylic acid (1,4-ADCA), 2,6-anthracene dicarboxylic acid (2,6-ADCA) and 9,10anthracene dicarboxylic acid (9,10-ADCA) -in a series of polar aprotic solvents using steadystate absorption, steady-state emission spectroscopy and time-correlated single photon counting emission lifetime spectroscopy. The addition of carboxylic acid functional groups on the anthracene ring perturbs the electronic transitions oriented along the longitudinal and transverse axes to varying degrees, resulting in differences in the photophysical properties. The three anthracene derivatives exhibit very different excited-state properties in basic solution compared to acidic and neutral solutions. Density functional theory (DFT) calculations reveal that the lowest-energy ground-state structures of both 2,6-ADCA and 1,4-ADCA have dihedral angles between the carboxylic acids and aromatic planes of θ = 0°. DFT calculations also indicate that there is a lower barrier for carboxyl group rotation for 1,4-ADCA (5.5 kcal/mol) than for 2,6-ADCA (8 kcal/mol) in the ground state. For 9,10-ADCA, the same dihedral angle increases to θ = 56.6°. Time-dependent DFT calculations suggest that the carboxyl groups of 1,4-ADCA and 2,6-ADCA remain coplanar with the anthracene ring system in the excited state. In contrast, the calculations reveal significant changes between the ground and excited geometries for 9,10-ADCA as the dihedrals decrease from 56.6º to 27.7° in the first excited state and puckering of the anthracene moiety of 9,10-ADCA is observed.

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“…The methods for the preparation of alkyne iminium salts 1, which can formally be derived from aldehydes or ketones -or more exactly from vinylogous amides -have mainly been developed by Maas et al [2][3][4][5][6][7][8]. Alkinyl-alkoxymethyleniminium salts 2 have been prepared by the alkylation of propiolamides with triethyloxonium tetrafluoroborate [9][10][11][12][13][14] or methyl fluorosulfonate [15]. The alkylation of propiolamidines seems to be of low value for the preparation of propiolamidinium salts [16].…”

Section: Introductionmentioning

confidence: 99%

Orthoamides and iminium salts, LXXXIX. Reactions of N,N,N′,N′,N″,N″,N′″,N′″-octamethyl-acetylene-bis(carboxamidinium) tetrafluoroborate with nucleophilic reagents – new methods for the preparation of amidinium salts and ketene aminalsa

Drandarov

Tiritiris

Kantlehner³

2015

Zeitschrift Für Naturforschung B

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The acetylene-bis(carboxamidinium) salt 4 dehydrates carboxylic acids to the corresponding anhydrides, as the byproduct 2-oxo-but-2-en-amidinium salt 6b was isolated. Aromatic hydroxy compounds and 2-furyl-methylmercaptan add to the triple bond of the salt 4 to give 2-aryloxy-and 2-alkylmercapto-but-2-enebis(amidinium) salts 7-9. According to this reaction principle, 2-organoamino-buten-2-ene-bis(amidinium) salts 10 and 11 were prepared from 4 and primary and secondary amines, whereas 4-chlorobenzhydrazide reacted with 4 to give the imidazole-3-carboxamidinium salt 13. The reaction of CH 2 -acidic compounds as malononitrile or ethyl cyanoacetate with the bis(amidinium) salt 4 affords 2-cyanomethylene-but-3-enamidinium salts 15. With the CH-acidic diethyl 2-bromomalonate, compound 4 undergoes a Michael-initiated ring closure cyclopropenation reaction with further ring opening by the released Br -to the corresponding 2-diethoxycarbonylmethylene-3-bromo-but-3-enamidinium salt 18. Unlike cyclopentadiene and furane, the reaction of N-methylpyrrole and bis(amidinium) salt 4 does not lead to Diels-Alder [4 + 2] cycloadduct but to the Michaeltype 1:1 adduct 20. Pyrrole-and thiophene-2-carboxamidinium salts 23-25 can be prepared from compound 4 and esters of glycine, N-methylglycine (sarcosine), and mercaptoacetic acid, respectively. The derivatives of quinoxaline-2-carboxamidinium salts 29 are accessible from aromatic 1,2-diamines and compound 4. The reaction of the CH 2 /NH-acidic cyanoacetamide with the bis(amidinium) salt 4 produced the 3-pyrroline-2-on derivatives 33.

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Nitration and oxidation of anthraquinone dimethyl derivatives

Cited by 10 publications

References 0 publications

Proton-Coupled Electron Transport in Anthraquinone-Based Zirconium Metal–Organic Frameworks

Proton-Coupled Electron Transport in Anthraquinone-Based Zirconium Metal–Organic Frameworks

Systematic investigation of the excited-state properties of anthracene-dicarboxylic acids

Orthoamides and iminium salts, LXXXIX. Reactions of N,N,N′,N′,N″,N″,N′″,N′″-octamethyl-acetylene-bis(carboxamidinium) tetrafluoroborate with nucleophilic reagents – new methods for the preparation of amidinium salts and ketene aminalsa

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