Vanadium(V) complexes of some bidentate hydrazone ligands and their bromoperoxidase activity

Adak, Piyali; Ghosh, Bipinbihari; Pakhira, Bholanath; Sekiya, Ryo; Kuroda, Reiko; Chattopadhyay, Shyamal Kumar

doi:10.1016/j.poly.2017.01.054

Cited by 27 publications

(8 citation statements)

References 59 publications

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“…These peroxo species ultimately cause oxidation of bromide, most probably, via hydroperoxide intermediate. The subsequent bromination of the substrate4, 29, 30c, 46, 47 takes place by oxidized bromine species (Br 2 , Br 3 − and/or HOBr). When the catalyst was not added to the reaction mixture, no brominated product was obtained.…”

Section: Resultsmentioning

confidence: 99%

Reactivity and Catalytic Activity of Homobimetallic Vanadium(V) Complex Derived from Bis(5‐chlorosalicylaldehyde)oxaloyldihydrazone Ligand

Syiemlieh

Asthana

Lal

2019

Applied Organom Chemis

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Homobimetallic vanadium(V) complex of the composition [(CH 3 ) 2 NH 2 + ] 2 [(VO 2 ) 2 (sloxCl)].4H 2 O was synthesized from the reaction of V 2 O 5 with bis(5-chlorosalicylaldehyde)oxaloyldihydrazone ligand in a 1:1 molar ratio in methanol. The structure of the complex was established by Xray crystallography. Reactivity of the complex with H 2 O 2 leads to bis (monooxidoperoxidovanadate(V)) [{VO(O 2 )} 2 (sloxCl)] 2− formation and withHCl, oxidohydroxido complex of composition [(VO (OH)(sloxCl)] 2− was formed. Binding interaction of the complex was also investigated toward protein (BSA) and it was found to be 2.21 x 10 8 M −1 . The catalytic activity of the complex in the oxidation of alcohols and oxidative bromination of some organic substrates was also studied, and it showed a great potent as a catalyst.

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Section: Resultsmentioning

confidence: 99%

Reactivity and Catalytic Activity of Homobimetallic Vanadium(V) Complex Derived from Bis(5‐chlorosalicylaldehyde)oxaloyldihydrazone Ligand

Syiemlieh

Asthana

Lal

2019

Applied Organom Chemis

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“…However, the decrease in product selectivity (%), as well as substrate conversion (%), was observed while using neat catalysts. Surprisingly, catalysts 3–6 show exceptionally high TOF values during the catalytic oxidative bromination of salicylaldehyde . The TOF values of the neat complexes are quite low in comparison to that of grafted catalysts (See Table ).…”

Section: Catalytic Activity 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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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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“…In contrast, the recent vanadium(V) investigations reported in the literature are focused on elucidating the behavior of hydrophobic complexes in terms of their interaction with erythrocytes, 16 interface model systems, their impact in anti-cancer activities 17 and enzyme inhibitors. 18 Moreover, vanadium(V) complexes derived from hydrazone compounds have been used as antimicrobial complexes 19 and also as catalysts for the oxidation of cyclohexane 20 and the oxidative bromination of salicylaldehyde, 21 which were rationalized using DFT and TDDFT calculations.…”

Section: Introductionmentioning

confidence: 99%

Stabilization of two conformers via intra- or inter-molecular hydrogen bonds in a dinuclear vanadium(v) complex with a pendant Schiff base: theoretical insight

et al. 2019

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Vanadium(V) complexes of some bidentate hydrazone ligands and their bromoperoxidase activity

Cited by 27 publications

References 59 publications

Reactivity and Catalytic Activity of Homobimetallic Vanadium(V) Complex Derived from Bis(5‐chlorosalicylaldehyde)oxaloyldihydrazone Ligand

Reactivity and Catalytic Activity of Homobimetallic Vanadium(V) Complex Derived from Bis(5‐chlorosalicylaldehyde)oxaloyldihydrazone Ligand

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

Stabilization of two conformers via intra- or inter-molecular hydrogen bonds in a dinuclear vanadium(v) complex with a pendant Schiff base: theoretical insight

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