Mimicking peroxidase activity by a polymer-supported oxidovanadium(IV) Schiff base complex derived from salicylaldehyde and 1,3-diamino-2-hydroxypropane

Maurya, Mannar R.; Chaudhary, Nikita; Avecilla, Fernando; Correia, Isabel

doi:10.1016/j.jinorgbio.2015.01.012

Cited by 29 publications

(14 citation statements)

References 30 publications

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“…Therefore, the catalytic efficiency of synthesized catalysts, PS‐[V V O 2 (Haeae‐sal)] ( 5 ) and PS‐[V V O 2 (Haeae‐hyap)] ( 6 ), was evaluated for the oxidation of thioanisole. Sulfone and sulfoxide were identified as two major products (shown in scheme ) for this reaction which are well reported in the literature …”

Section: Catalytic Activity Studiessupporting

confidence: 78%

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Synthesis and characterization of dimeric μ‐oxidovanadium complexes as the functional model of vanadium bromoperoxidase

Maurya

Mahato

Chaudhary

et al. 2020

Applied Organom Chemis

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Two vanadium (IV) complexes [VIVO(Haeae‐sal)(MeOH)]+ (1) and [VIVO(Haeae‐hyap)(MeOH)]+ (2) were prepared by reacting [VO(acac)2] with ligands [H2aeae‐sal] (I) and [H2aeae‐hyap] (II) respectively. Condensation of 2‐(2‐aminoethylamino)ethanol with salicylaldehyde and 2‐hydroxyacetophenone produces the ligands (I) and (II) respectively. Both vanadium complexes 1 and 2 are sensitive towards aerial oxygen in solution and rapidly convert into vanadium(V) dioxido species. Vanadium(V) dioxido species crystalizes as the dimeric form in the solid‐state. Single‐crystal XRD analysis suggests octahedral geometry around each vanadium center in the solid‐state. To access the benefits of heterogeneous catalysis, vanadium(V) dioxido complexes were anchored into the polymeric chain of chloromethylated polystyrene. All the synthesized neat and supported vanadium complexes have been studied by a number of techniques to confirm their structural and functional properties. Bromoperoxidase activity of the synthesized vanadium(V) dioxido complexes 3 and 4 was examined by carrying out oxidative bromination of salicylaldehyde and oxidation of thioanisole. In the presence of hydrogen peroxide, 3 shows 94.4% conversion (TOF value of 2.739 × 102 h−1) and 4 exhibits 79.0% conversion (TOF value of 2.403 × 102 h−1) for the oxidative bromination of salicylaldehyde where 5‐bromosalicylaldehyde appears as the major product. Catalysts 3 and 4 also efficiently catalyze the oxidation of thioanisole in the presence of hydrogen peroxide where sulfoxide is observed as the major product. Covalent attachment of neat catalysts 3 and 4 into the polymer chain enhances substrate conversion (%) and their catalytic efficiency increases many folds, both in the oxidative bromination and oxidation of thioether. Polymer supported catalysts 5 displayed 98.8% conversion with a TOF value of 1.127 × 104 h−1 whereas catalyst 6 showed 95.7% conversion with a TOF value of 4.675 × 103 h−1 for the oxidative bromination of salicylaldehyde. These TOF values are the highest among the supported vanadium catalysts available in the literature for the oxidative bromination of salicylaldehyde.

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Section: Catalytic Activity Studiessupporting

confidence: 78%

“…The average surface roughness of complex 5 and 6 is 3.21 nm and 2.88 nm, respectively. Due to the anchoring of metal complexes into the pores of the polymer chain during heterogenization causes the reduction in surface roughness . Hence, surface roughness can be correlated with the percentage of metal loading into the polymer.…”

Section: Theoretical Studiesmentioning

confidence: 99%

Synthesis and characterization of dimeric μ‐oxidovanadium complexes as the functional model of vanadium bromoperoxidase

Maurya

Mahato

Chaudhary

et al. 2020

Applied Organom Chemis

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“…Indeed, the pH‐controlled protonation or deprotonation of the phenolic groups gives the possibility to obtain compounds with different numbers of metal centres and coordination geometries, giving rise to synthesis of homometallic or heterometallic complexes . These compounds are also of interest for their catalytic properties and as models of biological systems …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Electronic, Magnetic and Structural Characterization of New Trinuclear Mixed‐Valence Co^III‐Co^II‐Co^III Complex.

et al. 2016

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The structural, electronic, magnetic and theoretical study of the complex [Co3(HL)2(μ‐AcO)2(AcO)2], 1, (HL is the dianion obtained by deprotonation of N,N’‐bis(salicylidene)‐2‐hydroxy‐1,3‐propanediamine and AcO is acetate) shows that 1 crystallizes with two independent molecules in the asymmetric unit. Each molecule is a trinuclear complex. Both molecules have similar geometry, and correspond to a spin system based on trapped mixed valences on six‐coordinate metal centres, CoIII(s=0)‐CoII(s=3/2)‐CoIII(s=0). The rigid framework formed by the tetradentate Salen‐type ligands HL and the syn‐syn bridging acetate anions is a characteristic feature observed in other related complexes. However, the here reported compound is the first one in this family having Z’>1. UV‐Vis spectrum shows a broad band in the visible region where d‐d transition for ions CoIII and CoII are. EPR spectra and the electronic energy estimations of the ground state show the presence of two conformers s=3/2. The χMT product at 300 K is 3.24 emu mol−1K per trinuclear unit, this product is expected for CoII where the contribution of orbital angular moment is taken into account (3.38 emu mol−1K for L=3).

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“…By reacting PS‐Cl with 1–4 , surface roughness reduces to 5.94 nm, 6.80 nm, 3.86 nm and 4.04 nm, respectively. This is because of the fact that through covalent attachment of neat complexes into the polymer matrix, beads pores are occupied by complexes and hence reduces the porosity and consequently roughness is reduced . The extent of roughness reduction can be correlated with the higher metal complex loading into the pore of the polymer beads.…”

Section: Resultsmentioning

confidence: 99%

Polymer‐anchored mononuclear and binuclear Cu^II Schiff‐base complexes: Impact of heterogenization on liquid phase catalytic oxidation of a series of alkenes

Maurya

Kesharwani

Kachhap

et al. 2019

Applied Organom Chemis

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Liquid phase catalytic oxidation of a number of alkenes, for example, cyclohexene, cis‐cyclooctene, styrene, 1‐methyl cyclohexene and 1‐hexene, was performed using polymer‐anchored copper (II) complexes PS‐[Cu (sal‐sch)Cl] (5), PS‐[Cu (sal‐tch)Cl] (6), PS‐[CH2{Cu (sal‐sch)Cl}2] (7) and PS‐[CH2{Cu (sal‐tch)Cl}2] (8). Neat complexes [Cu (sal‐sch)Cl] (1), [Cu (sal‐tch)Cl] (2), [CH2{Cu (sal‐sch)Cl}2] (3) and [CH2{Cu (sal‐tch)Cl}2] (4) were isolated by reacting CuCl2·2H2O with [Hsal‐sch] (I), [Hsal‐tch] (II), [H2bissal‐sch] (III) and [H2bissal‐tch] (IV), respectively, in refluxing methanol. Complexes 1–4 have been covalently anchored in Merrifield resin through the amine nitrogen of the semicarbazide or thiosemicarbazide moiety. A number of analytical, spectroscopic and thermal techniques, such as CHNS analysis, Fourier transform‐infrared, UV–Vis, PMR, 13C‐NMR, electron paramagnetic resonance, scanning electron microscopy, energy‐dispersive X‐ray analysis, thermogravimetric analysis, atomic force microscopy, atomic absorption spectroscopy, and electrospray ionization‐mass spectrometry, were used to analyze and establish the molecular structure of the ligands (I)–(IV) and complexes (1)–(8) in solid state as well as in solution state. Grafted complexes 5–8 were employed as active catalysts for the oxidation of a series of alkenes in the presence of hydrogen peroxide. Copper hydroperoxo species ([CuIII (sal‐sch)‐O‐O‐H]), which is believed to be the active intermediate, generated during the catalytic oxidation of alkenes, are identified. It was found that supported catalysts are very economical, green and efficient in contrast to their neat complexes as well as most of the recently reported heterogeneous catalysts.

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Mimicking peroxidase activity by a polymer-supported oxidovanadium(IV) Schiff base complex derived from salicylaldehyde and 1,3-diamino-2-hydroxypropane

Cited by 29 publications

References 30 publications

Synthesis and characterization of dimeric μ‐oxidovanadium complexes as the functional model of vanadium bromoperoxidase

Synthesis and characterization of dimeric μ‐oxidovanadium complexes as the functional model of vanadium bromoperoxidase

Synthesis, Electronic, Magnetic and Structural Characterization of New Trinuclear Mixed‐Valence Co^III‐Co^II‐Co^III Complex.

Polymer‐anchored mononuclear and binuclear Cu^II Schiff‐base complexes: Impact of heterogenization on liquid phase catalytic oxidation of a series of alkenes

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Mimicking peroxidase activity by a polymer-supported oxidovanadium(IV) Schiff base complex derived from salicylaldehyde and 1,3-diamino-2-hydroxypropane

Cited by 29 publications

References 30 publications

Synthesis and characterization of dimeric μ‐oxidovanadium complexes as the functional model of vanadium bromoperoxidase

Synthesis and characterization of dimeric μ‐oxidovanadium complexes as the functional model of vanadium bromoperoxidase

Synthesis, Electronic, Magnetic and Structural Characterization of New Trinuclear Mixed‐Valence CoIII‐CoII‐CoIII Complex.

Polymer‐anchored mononuclear and binuclear CuII Schiff‐base complexes: Impact of heterogenization on liquid phase catalytic oxidation of a series of alkenes

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Product

Resources

About

Synthesis, Electronic, Magnetic and Structural Characterization of New Trinuclear Mixed‐Valence Co^III‐Co^II‐Co^III Complex.

Polymer‐anchored mononuclear and binuclear Cu^II Schiff‐base complexes: Impact of heterogenization on liquid phase catalytic oxidation of a series of alkenes