Synthesis, structural and magnetic characterizations of a dinuclear copper(II) complex with an (N,S,O) donor ligand: Catecholase and phenoxazinone synthase activities

Ghosh, Ayon Kanti; Ali, Anzar; Singh, Yogesh; Purohit, Chandra Shekhar; Ghosh, Rajarshi

doi:10.1016/j.ica.2018.02.004

Cited by 24 publications

(7 citation statements)

References 36 publications

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“…An attempt was also made to examine the reactivity of the synthesized copper complexes with a comparison of the kinetic parameter for other reported copper complexes. [5,47,56,59,[62][63][64] The kinetics parameter are furnished in Table 2.…”

Section: Catalytic Oxidation Studies Of 2-aminophenol and Mechanistic Inferencesmentioning

confidence: 99%

Copper(II) complexes with a benzimidazole functionalized Schiff base: Synthesis, crystal structures, and role of ancillary ions in phenoxazinone synthase activity

Mudi

Mahato

Joshi

et al. 2021

Applied Organom Chemis

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This research study reports the synthesis, structural characterization and phenoxazinone synthase-like activity of two structurally similar copper(II) complexes developed with a benzimidazole functionalized Schiff base (L). The ligand, L, was designed and synthesized in high yield by the reaction of p-methoxy benzaldehyde with o-phenylenediamine. The reaction of L with CuCl 2 and Cu(NO 3 ) 2 leads to the formation of two isostructural complexes, [Cu(L) 2 Cl 2 ] 2 (1) and [Cu(L) 2 (NO 3 ) 2 ] 2 (2). Single crystal X-ray structural study reveals that both the Cu(II) centre in 1 and 2 adopts a square planar geometry. An attempt has also been made to understand the role of coordinated coligands on the catalytic oxidation of 2-aminophenol (2-AP) to 2-amino-3Hphenoxazine-3-one (2-APX) in methanol. The presence of coordinated nitrate to Cu(II) ions imparts a more labile character to complex 2, and the catalytic efficiency (k cat /K M ) for complex 2 (1.50 × 10 7 ) was determined almost double compared with that of complex 1 (8.78 × 10 6 ). Electro-chemical and electrospray ionization mass spectrometry studies of 1 and 2 with 2-AP suggests that the square planar geometries of the Cu(II) centres remain the driving force to develop enzyme-substrate adducts and excellent catalytic performance of the complexes. Electrochemical and EPR spectral analysis of the reaction mixture confirm the presence of active 2-AP − /2-AP •− redox species in the course of catalytic oxidation and suggest the radical driven oxidative coupling of 2-AP in an aerobic environment. Temperature-dependent kinetic measurements were carried out to evaluate the activation parameters (E a , ΔH ‡ , ΔS ‡ ), which favours the higher rate of catalytic oxidation of 2-AP for complex 2 than complex 1.

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Section: Catalytic Oxidation Studies Of 2-aminophenol and Mechanistic Inferencesmentioning

confidence: 99%

Copper(II) complexes with a benzimidazole functionalized Schiff base: Synthesis, crystal structures, and role of ancillary ions in phenoxazinone synthase activity

Mudi

Mahato

Joshi

et al. 2021

Applied Organom Chemis

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“…1,4,10,11 Model complexes have played an important role in understanding the structural, spectroscopic and catalytic properties of the copper sites in protiens. [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] Various workers have tried to rationalize the catalytic efficiency of the catechol oxidation reaction with variety of parameters like redox potentials, solvent effect, pH of the medium, number and nature of bridging ligands, effect of secondary coordination sphere etc., however our knowledge in this direction is still sketchy and incomplete. 12,13,[17][18][19][20][21][22][23][24][25][26] Therefore, there is need for study of new model complexes showing catecholase activity and exploration of relationship between their structural, spectroscopic and catalytic properties.…”

Section: Introductionmentioning

confidence: 99%

Cu(ii) complexes of a tridentate N,N,O-donor Schiff base of pyridoxal: synthesis, X-ray structures, DNA-binding properties and catecholase activity

et al. 2018

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“…Where A comparison of catalytic oxidation of 2-AP by this Cu (II) complex with some other reported Cu (II) complexes is tabulated in Table 3. [26c, [45][46][47] The catalytic efficiency for the oxidative dimerization of 2-AP by this Cu (II) complex was found high as k cat / K M = 5.67 × 10 5 . Electrochemical analysis and EPR studies were vperformed to understand the catalytic behaviour of Cu (II) complex in the oxidative dimerization of 2-AP in acetonitrile medium.…”

Section: Phenoxazinone Synthase Mimicking Activity Of the Copper (Imentioning

confidence: 90%

“…Where, V is rate of the reaction, K m is denoted as Michaelis-Menten constant, V max is the maximum velocity of the reaction, and A comparison of catalytic oxidation of 2-AP by this Cu (II) complex with some other reported Cu (II) complexes is tabulated in Table 3. [26c, [45][46][47] The catalytic efficiency for the oxidative dimerization of 2-AP by this Cu (II) complex was found high as k cat / K M = 5.67 × 10 5 .…”

Section: Phenoxazinone Synthase Mimicking Activity Of the Copper (Ii)...mentioning

confidence: 90%

Ligand directed synthesis of a unprecedented tetragonalbipyramidal copper (II) complex and its antibacterial activity and catalytic role in oxidative dimerisation of 2‐aminophenol

Mahato

Meheta

Kotakonda

et al. 2020

Applied Organom Chemis

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In pursuit of the significant contribution of copper ion in different biological processes, this research work describes the synthesis, X-ray structure, Hirshfeld surface analysis, oxidative dimerization of 2-aminophenol and antibacterial activity of a newly designed copper (II)-Schiff base complex, [Cu(L) 2 ] (1), [Schiff base (HL) = 2-(2-methoxybenzylideneamino)phenol]. X-ray structural analysis of 1 reveals that the Cu (II) complex crystallizes in a cubic crystal system with Ia-3d space group. The Cu (II) centre adopts an unprecedented tetragonal bipyramidal geometry in its crystalline phase. The Schiff base behaves as a tridentate chelator and forms an innermetallic chelate of first order with Cu (II) ion. The copper (II) complex has been tested in the bio-mimics of phenaxozinone synthase activity in acetonitrile and exhibits good catalytic activity as evident from high turnover number, 536.4 h −1. Electrochemical analysis exhibits the appearance of two additional peaks at −0.15 and 0.46 V for Cu (II) complex in presence of 2-AP and suggests the development of AP − /AP •− and AP •− /IQ redox couples in solution, respectively. The presence of iminobenzosemiquinone radical at g = 2.057 in the reaction mixture was confirmed by electron paramagnetic resonance and may be considered the driving force for the oxidative dimerisation of 2-AP. The existence of a peak at m/z 624.81 for Cu (II) complex in presence of 2-AP in electrospray ionization mass spectrum ensures that the catalytic oxidation proceeds through enzyme-substrate adduct formation. The copper (II) complex exhibits potential antibacterial properties against few pathogenic bacterial species like Staphylococcus aureus, Enterococcus and Klebsiella pneumonia and scanning electron microscope studies consolidates that destruction of bacterial cell membrane accounts on the development of antibacterial activity. Shreya Mahato and Nishith Meheta have equal contribution.

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Synthesis, structural and magnetic characterizations of a dinuclear copper(II) complex with an (N,S,O) donor ligand: Catecholase and phenoxazinone synthase activities

Cited by 24 publications

References 36 publications

Copper(II) complexes with a benzimidazole functionalized Schiff base: Synthesis, crystal structures, and role of ancillary ions in phenoxazinone synthase activity

Copper(II) complexes with a benzimidazole functionalized Schiff base: Synthesis, crystal structures, and role of ancillary ions in phenoxazinone synthase activity

Cu(ii) complexes of a tridentate N,N,O-donor Schiff base of pyridoxal: synthesis, X-ray structures, DNA-binding properties and catecholase activity

Ligand directed synthesis of a unprecedented tetragonalbipyramidal copper (II) complex and its antibacterial activity and catalytic role in oxidative dimerisation of 2‐aminophenol

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