Catalytic activity of a benzoyl hydrazone based dimeric dicopper(II) complex in catechol and alcohol oxidation reactions

Anbu, Sellamuthu; Alegria, Elisabete C. B. A.; Pombeiro, Armando J. L.

doi:10.1016/j.ica.2014.11.038

Cited by 21 publications

(3 citation statements)

References 70 publications

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“…For this complex K cat data was found to be better than the data reported by Anbu et. al, Bouwman and co‐workers, and Thio et. al, however, the value of K cat was found to be lower than the values reported by Das and co‐workers and Wegner et.…”

Section: Resultsmentioning

confidence: 95%

Water‐Soluble Copper Complex Derived from Ligand TETA^TA Having NNN Donors: Studies on Rapid Degradation of Organic Dyes, Catecholase and Phenoxazinone Synthase Activities

2018

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Water-soluble copper complex [Cu(TETA TA )(Cl 2 )] (1) derived from tridentate ligand (TETA TA ) (L= 2-(2-((2-((2-aminoethyl)amino) ethyl)-amino)ethyl)isoindoline-1,3-dione) having NNN donor, was synthesized, characterized and its molecular structure was determined using X-ray crystallography. This water soluble copper complex was found to be an efficient catalyst for rapid degradation of organic dyes like orange II, rhodamine B and methylene blue dyes were investigated. This catalyst was also utilised for the oxidation of catechol, giving rise to catecholase activity as well as oxidative coupling of 2-aminophenol providing phenoxazinone synthase activity. DFT and TD-DFT calculations were performed to understand the electronic properties of this molecule using B3LYP/LANL2DZ basis set. Results and discussion Synthesis and characterizationMetal complex [Cu(TETA TA )(Cl 2 )](1) was synthesized via template synthesis utilizing CuCl 2 .2H 2 O, N,N'-Bis(2-aminoethyl)ethane-1,2-diamine and phthalic anhydride in methanol (shown in [a] O.

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Section: Resultsmentioning

confidence: 95%

Water‐Soluble Copper Complex Derived from Ligand TETA^TA Having NNN Donors: Studies on Rapid Degradation of Organic Dyes, Catecholase and Phenoxazinone Synthase Activities

2018

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“…The catalytic conversion of 3,5-DTBC to 3,5-DTBQ (Scheme 2) has already been investigated by a number of scientist as a model catalytic reaction by using a variety of mono-, [45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60] di-, 31,[51][52][53][54][55][56][57][58][59][60][61][62][63] tri/tetra-, [64][65][66] and poly-nuclear metal complexes. 67 3,5-DTBC is the most widely used model substrate in catalytic oxidation process due to its low redox potential value that favours the oxidation to 3,5-DTBQ, which shows absorbance maximum at 400 nm in DMSO.…”

Section: Oxidation Of 35-di-tert-butylcatechol (Kinetics Studies)mentioning

confidence: 99%

Catecholase-Like Activity and Theoretical Study in Solid State of a New Ru(III)-Schiff Base Complex

Biswas

Saha

Zangrando

et al. 2021

ACSi

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A new ruthenium(III) complex of molecular formula [Ru(PPh3)Cl2(L)] (1) has been synthesized using the Schiff base ligand obtained from 5-chlorosalicylaldehyde and N,N-dimethylethylenediamine and characterized by FT-IR, UV-Vis, cyclic voltammetry and single crystal X-ray structural analysis. The metal ion exhibits a slightly distorted octahedral environment where the chelating Schiff base ligand contributes with its NNO donor set. The coordination geometry around the Ru(III) ion is completed by a PPh3 ligand and two chloride anions, and the charge balance is assured by the phenoxo oxygen of the Schiff base. With the aim to analyse the energy related to the halogen bonding interactions in solid state, a theoretical study has been performed on complex 1, by using the MEP and NCl plot computational tools. Furthermore, complex 1 shows catecholase-like activity in conversion of the model substrate 3,5-di-tert-butylcatechol (3,5-DTBC) to the corresponding 3,5-di-tert-butylquinone (3,5-DTBQ) under aerobic condition. The parameters regarding the enzymatic kinetics have been evaluated from the Lineweaver-Burk plot using the Michaelis-Menten approach of enzyme catalysis. A significant high T.O.N value (2.346 × 103 h–1) indicates that complex 1 has a very good catalytic efficiency towards 3,5-DTBC.

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“…3,5-Di-tert-butylcatechol (2a). 33,34 It was obtained in 2 h; eluent: hexane/ethyl acetate 8:2, 38.0 mg, yield = 95%. 1 3-(3,4-Dihydroxyphenyl)-propionic Acid Methyl Ester (2e).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones

et al. 2019

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Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.

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Catalytic activity of a benzoyl hydrazone based dimeric dicopper(II) complex in catechol and alcohol oxidation reactions

Cited by 21 publications

References 70 publications

Water‐Soluble Copper Complex Derived from Ligand TETA^TA Having NNN Donors: Studies on Rapid Degradation of Organic Dyes, Catecholase and Phenoxazinone Synthase Activities

Water‐Soluble Copper Complex Derived from Ligand TETA^TA Having NNN Donors: Studies on Rapid Degradation of Organic Dyes, Catecholase and Phenoxazinone Synthase Activities

Catecholase-Like Activity and Theoretical Study in Solid State of a New Ru(III)-Schiff Base Complex

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones

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Catalytic activity of a benzoyl hydrazone based dimeric dicopper(II) complex in catechol and alcohol oxidation reactions

Cited by 21 publications

References 70 publications

Water‐Soluble Copper Complex Derived from Ligand TETATA Having NNN Donors: Studies on Rapid Degradation of Organic Dyes, Catecholase and Phenoxazinone Synthase Activities

Water‐Soluble Copper Complex Derived from Ligand TETATA Having NNN Donors: Studies on Rapid Degradation of Organic Dyes, Catecholase and Phenoxazinone Synthase Activities

Catecholase-Like Activity and Theoretical Study in Solid State of a New Ru(III)-Schiff Base Complex

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones

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Water‐Soluble Copper Complex Derived from Ligand TETA^TA Having NNN Donors: Studies on Rapid Degradation of Organic Dyes, Catecholase and Phenoxazinone Synthase Activities

Water‐Soluble Copper Complex Derived from Ligand TETA^TA Having NNN Donors: Studies on Rapid Degradation of Organic Dyes, Catecholase and Phenoxazinone Synthase Activities