Synthesis, characterization and quantum chemical investigation of molecular structure and vibrational spectra of 2,5-dichloro-3,6-bis-(methylamino)1,4-benzoquinone

Gautam, Bhanu Pratap Singh; Srivastava, Mona; Прасад, Рам; Yadav, R.A.

doi:10.1016/j.saa.2014.02.082

Cited by 24 publications

(10 citation statements)

References 28 publications

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“…It is essential for the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in researching the chemical stability of molecules. [70,71] The ability of electron donating and accepting can be characterized by the energy of HOMO and LUMO. As shown in Figure 5a, the LUMO+1, LUMO, HOMO, HOMO−1, HOMO−2, and HOMO−3 energies of H 12 Sub-PcB-OPh 2 OH had been calculated at the B3LYP/6-31G (d) level; the values were observed to be −2.431, −2.443, −5.174, −5.328, −6.535, and −6.563 eV, respectively, corresponding to HOMO-LUMO gap of 2.731 eV.…”

Section: Dft and Td-dft Calculation Analysismentioning

confidence: 99%

Novel axial substituted subphthalocyanine sensitized titanium dioxide H₁₂SubPcB‐OPh₂OH/TiO₂ photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

Yang

Zhang

et al. 2021

Applied Organom Chemis

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Utilizing subphthalocyanine (SubPc) and 4,4 0 -dihydroxybiphenyl (C 12 H 10 O 2 ) as the raw materials, an innovative axial substituted SubPc H 12 SubPcB-OPh 2 OH was synthesized by solvothermal method. The density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations were employed to further study the properties and structures of H 12 SubPcB-OPh 2 OH. To expand photocatalytic activities for organic dyes degradation, H 12 SubPcB-OPh 2 OH was decorated onto surface of TiO 2 nanoparticles to fabricate high-efficiency H 12 SubPcB-OPh 2 OH/TiO 2 photosensitive catalysts. The degradation experiments indicated that the H 12 SubPcB-OPh 2 OH/TiO 2 catalyst with the mass ratio of 1:25 had the greatest performance in the elimination of methyl orange (MO), bromophenol blue (BB), methylene blue (MB), and acid fuchsin (AF). The 29.4%, 72.5%, 27.6%, and 64.8% of MO, BB, MB, and AF was removed by pure TiO 2 in 180-min, respectively. Under the same conditions, the photocatalytic rate of H 12 SubPcB-OPh 2 OH/TiO 2 can reach 96.3%, 99.5%, 97.5%, and 99.5%, separately. The efficiency of the as-synthesized composite was 3.3, 1.4, 3.5, and 1.5 times higher than that over bare TiO 2 for MO, BB, MB, and AF degradation under visiblelight irradiation, respectively. Besides, after five cycles of experiments, the degradation rate of H 12 SubPcB-OPh 2 OH/TiO 2 photocatalyst to BB can still reach 90.2%, which demonstrated that the obtained photocatalysts possessed remarkable stability and is much higher than 15.6% of pure TiO 2 . This study provides a new idea to the construction of photosensitive catalysts based on TiO 2 for water purification.

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Section: Dft and Td-dft Calculation Analysismentioning

confidence: 99%

Novel axial substituted subphthalocyanine sensitized titanium dioxide H₁₂SubPcB‐OPh₂OH/TiO₂ photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

Yang

Zhang

et al. 2021

Applied Organom Chemis

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“…The crude mixture was then purified by column chromatography on silica gel (stationary phase) with chloroform (mobil phase) to afford product 20: R f = 0.4 (CHCl 3 ); Yield: 60% (51 mg); Dark red viscous oil; IR (ATR): 3305, 2956, 2918, 2849, 1668, 1552, 1498, 1287; 1 H NMR (CDCl 3 ) δ: 8.15 (1H, dd, CH napht , 3 J = 7.81 Hz, 4 J =0.98 Hz); 8.04 (1H, dd, CH napht , 3 J = 7.81 Hz, 4 J = 0.97 Hz); 7.63 (td, 1H, CH napht , 3 J = 7.81 Hz, 4 J = 0.98 Hz); 7.72 (td, 1H, CH napht , 3 J = 7.81 Hz, 4 J = 0.98 Hz); 6.70-6.80 (brs, 1H, NH), 4.14 (t, 2H, NH-CH 2 , The reaction between chloranil and primary/secondary amines gives the NH-/N-substituted quinones. Some examples of such reactions have been previously described [51][52][53][54]. For example, Singh Gautam BP et al synthesized and characterized the compound 2,5-dichloro-3,6-bis-(methylamino)-1,4-benzoquinone, which was capable of forming molecular complexes like chloranilic acid [54].…”

Section: Synthesis Of 2-(2-(methylthio)ethylamino)-3-(dodecylthio)naphthalene-14-dione (20)mentioning

confidence: 99%

“…Some examples of such reactions have been previously described [51][52][53][54]. For example, Singh Gautam BP et al synthesized and characterized the compound 2,5-dichloro-3,6-bis-(methylamino)-1,4-benzoquinone, which was capable of forming molecular complexes like chloranilic acid [54]. In this work, compounds 6 and 7, having mono-NH-substituted-tri-chloro-1,4-benzoquinone and 2,5-dichloro-3,6-bis(NH-substituted)-1,4-benzoquinone structures, respectively, were synthesized by the reaction of 1:1 molar ratio of p-chloranil 1 with (-)-cis-myrtanylamine 5 in dichloromethane at room temperature.…”

Section: Synthesis Of 2-(2-(methylthio)ethylamino)-3-(dodecylthio)naphthalene-14-dione (20)mentioning

confidence: 99%

Synthesis of some NH- and NH,S- substituted 1,4-quinones

Kaçmaz

2021

Turk J Chem

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IntroductionQuinones are widespread in nature [1,2] (in plants, fungi, bacteria etc.), and many synthetic or natural quinones possess various pharmacological properties including anticancer [3][4][5], antibacterial [6], antifungal [6], antiinflammatory [7], antimycobacterial [8], and molluscicidal [9] activities. Moreover, substituents such as halogen, amino, thio groups of the synthetic quinone derivatives can increase their pharmacological activities, such as antibacterial, cytotoxic, and antiproliferative [3,10,11]. Quinonoid systems' pharmacological specialties are related to their capacity to produce free radicals or semiquinones in redox reactions [11][12][13].Among quinones, 1,4-naphthoquinone scaffold are found in many natural or synthetic products such as menadione, juglone, plumbagin, alkannin, and shikonin [14-16]. In addition, 1,4-naphthoquinone derivatives have receieved a considerable interest in biological applications with their antibacterial [11], antiatherosclerosis [17], antiinflammatory [18], anticancer [5,18], and cytotoxic [19] activities. Thus, many reports on the reactions of 1,4-naphthoquinones with amines [3,5,13], anilines [11,20], phenols [21], thiols [3,5,22], aminopyridine [23], alcohol [24,25], glycol [25] are available in the literature. In this study, compounds 10, 12, 13, 15, 17, and 19, 20 have NH-and NH,SR-substituted-1,4-naphthoquinone skeleton, respectively.The literature mentions some aminobenzocrown ethers [26,27] similar to 15 and 17. For example, N-(2-chloro-1,4naphthoquinon-3-yl)-4'-aminobenzocrown ethers were synthesized from the reaction between 4'-aminobenzocrown ethers and 2,3-dichloro-1,4-naphthoquinone [26], and thus in the present study, synthesis of 15 and 17 contribute to crown-containing naphthoquinones, carrying out the reaction between crown ethers (14 and 16) and 2-bromo-1,4naphthoquinone (4). Moreover, crown-containing naphthoquinone 19 was synthesized, including both amino and thio substituents, together.1,4-benzoquinones, including NH-, methoxy, thio, alkyl or aryl groups, have been the subject of study due to their properties such as antimicrobial [28], antibacterial [29], cytotoxic [30][31][32], potential urease inhibitor [33], and potent inhibitory activity towards enzyme system [34]. In addition, some of studies on the formation of N(H)-, SR-, alkoxy substituted-1,4-benzoquinones have been reported in the literature [34][35][36][37][38]. Among 1,4-benzoquinones, halogenanils, such as chloranil, with amines yield amination products of quinones. For example, Wu H et al. reported tetrathiafulvalenequinone dyad, having mono-NH-substituted-tri-chloro-1,4-benzoquinone structure [38]. In another example, Sing and et al. synthesized [39] new coordination polymers, starting from 2,5-dichloro-3,6-bis(ethylamino)-1,4-benzoquinone. In this study, compounds 6 and 7 have mono-NH-substituted-tri-chloro-1,4-benzoquinone and 2,5-dichloro-3,6-bis(NH-

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“…In the detection system, the fluorescent intensity of CDs decreased over time in the existence of increasing DA quinone. Quinone structure exists widely in the organism and it is known that naturally occurring quinones play an essential role in electron transport in bacterial reaction center and mitochondria [26,27]. Therefore, it is important to understand the influence of quinone structure on the fluorescence of CDs.…”

Section: Detection Of Quinone Structurementioning

confidence: 99%

Sensitive detection of dopamine and quinone drugs based on the quenching of the fluorescence of carbon dots

Ren

Meng

et al. 2016

Science Bulletin

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Synthesis, characterization and quantum chemical investigation of molecular structure and vibrational spectra of 2,5-dichloro-3,6-bis-(methylamino)1,4-benzoquinone

Cited by 24 publications

References 28 publications

Novel axial substituted subphthalocyanine sensitized titanium dioxide H₁₂SubPcB‐OPh₂OH/TiO₂ photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

Novel axial substituted subphthalocyanine sensitized titanium dioxide H₁₂SubPcB‐OPh₂OH/TiO₂ photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

Synthesis of some NH- and NH,S- substituted 1,4-quinones

Sensitive detection of dopamine and quinone drugs based on the quenching of the fluorescence of carbon dots

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Synthesis, characterization and quantum chemical investigation of molecular structure and vibrational spectra of 2,5-dichloro-3,6-bis-(methylamino)1,4-benzoquinone

Cited by 24 publications

References 28 publications

Novel axial substituted subphthalocyanine sensitized titanium dioxide H12SubPcB‐OPh2OH/TiO2 photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

Novel axial substituted subphthalocyanine sensitized titanium dioxide H12SubPcB‐OPh2OH/TiO2 photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

Synthesis of some NH- and NH,S- substituted 1,4-quinones

Sensitive detection of dopamine and quinone drugs based on the quenching of the fluorescence of carbon dots

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Novel axial substituted subphthalocyanine sensitized titanium dioxide H₁₂SubPcB‐OPh₂OH/TiO₂ photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

Novel axial substituted subphthalocyanine sensitized titanium dioxide H₁₂SubPcB‐OPh₂OH/TiO₂ photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties