Synthesis, Characterization and Biomimetic Activity of Heterogenized Dioxidomolybdenum(VI) Complex and Its Homogeneous Analogue

Cis -[Mo VI O 2 (CH 3 -hptb)(MeOH)] ( 1 ) has been synthesized by the reaction of [Mo VI O 2 (acac) 2 ] and deferasirox [ICL670: 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid, H 3 hptb, I ] in 1:1 molar ratio in MeOH. Complex 1 has been characterized successfully by several spectral...

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Bibliographic Details
Published in:Topics in catalysis 2023-03, Vol.66 (5-8), p.420-434
Main Authors: Maurya, Mannar R., Chauhan, Abhilasha
Format: Article
Language:English
Subjects:
Benzoic acid
Biomimetics
Bromination
Catalysis
Catalysts
Characterization and Evaluation of Materials
Chemical synthesis
Chemistry
Chemistry and Materials Science
Conversion
Esterification
Hydrogen peroxide
Industrial Chemistry/Chemical Engineering
NMR
Nuclear magnetic resonance
Original Paper
Oxidizing agents
Pharmacy
Physical Chemistry
Room temperature
Spectral methods
Styrenes
Thermogravimetric analysis
Thymol
Titanium dioxide
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Summary:Cis -[Mo VI O 2 (CH 3 -hptb)(MeOH)] ( 1 ) has been synthesized by the reaction of [Mo VI O 2 (acac) 2 ] and deferasirox [ICL670: 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid, H 3 hptb, I ] in 1:1 molar ratio in MeOH. Complex 1 has been characterized successfully by several spectral techniques, viz. FT-IR, UV–Vis, 1 H and 13 C NMR, elemental (CHN) and thermogravimetric analysis. The esterification of the carboxylic group of ligand was observed during the complexation process with molybdenum. The analogous heterogeneous complex [Mo VI O 2 (hptb)(MeOH)]@APTMS-TiO 2 ( 2 ) has been synthesized by immobilizing I on amine-functionalized TiO 2 , {[H 2 hptb]@APTMS-TiO 2 ( II )} and then reacting it with [Mo VI O 2 (acac) 2 ] in MeOH. Characterization of the immobilized complex was achieved through FT-IR, DRS, P-XRD, TEM, thermogravimetric analysis and MP-AES. Both the complexes have been utilized in synthesizing organobromine compounds through oxidative bromination of styrene in the presence of KBr, oxidant (30% aq. H 2 O 2 ) and 70% aq. HClO 4 at room temperature. With the formation of 2-bromo-1-phenylethane-1-ol and 1-phenylethane-1,2-diol under the optimized reaction conditions, 72 and 100% conversion of styrene was achieved in the presence of catalysts 1 and 2 , respectively. The oxidative bromination of thymol with catalyst 2 provides 2-bromothymol (52%) and 2,4-dibromothymol (48%) with 100% conversion. Graphical Abstract Dioxidomolybdenum(VI) complex of ICL670 immobilized on amine-functionalized titania has been synthesized and used as a functional model of haloperoxidases for the oxidative bromination of thymol and styrene.
ISSN:1022-5528
1572-9028
DOI:10.1007/s11244-022-01747-7