Water-soluble Al(), Fe() and Cu() formazanates: synthesis, structure, and applications in alkane and alcohol oxidations

A series of water-soluble metal formazanates, [Al 2 (OH) 2 (H 2 O) 8 ](HL) 2 ( 1 ), [{Fe(H 2 O) 4 }(HL)(H 2 L)]·2H 2 O ( 2 ) and [Cu(en) 2 (H 2 O) 2 ][CuL(H 2 O) 2 ] 2 ( 3 ), were synthesized by the reaction of sodium 2-(2-(( E )-cyano(( E )-(2-sulfonatophenyl)diazenyl)methylene)hydrazineyl) benzene...

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Bibliographic Details
Published in:New journal of chemistry 2022-03, Vol.46 (11), p.52-511
Main Authors: Gurbanov, Atash V, Andrade, Marta A, Martins, Luísa M. D. R. S, Mahmudov, Kamran T, Pombeiro, Armando J. L
Format: Article
Language:English
Subjects:
Alkanes
Aluminum
Catalysts
Chemical synthesis
Coordination compounds
Copper
Cyclohexane
Cyclohexanone
Ethylenediamine
Ferric chloride
Hydrogen peroxide
Infrared spectroscopy
Iron
NMR
Nuclear magnetic resonance
Oxidation
Room temperature
Water chemistry
X ray analysis
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Summary:A series of water-soluble metal formazanates, [Al 2 (OH) 2 (H 2 O) 8 ](HL) 2 ( 1 ), [{Fe(H 2 O) 4 }(HL)(H 2 L)]·2H 2 O ( 2 ) and [Cu(en) 2 (H 2 O) 2 ][CuL(H 2 O) 2 ] 2 ( 3 ), were synthesized by the reaction of sodium 2-(2-(( E )-cyano(( E )-(2-sulfonatophenyl)diazenyl)methylene)hydrazineyl) benzenesulfonate ( Na 2 HL ) with Al(NO 3 ) 3 ·9H 2 O, FeCl 3 ·6H 2 O and Cu(NO 3 ) 2 ·3H 2 O (in the presence of ethylenediamine) in methanol, respectively. The formazan pro-ligand Na 2 HL and its complexes 1-3 were characterized by ESI-MS, 1 H/ 13 C NMR (for Na 2 HL ), IR spectroscopy, elemental and X-ray diffraction analyses (for 1-3 ). According to the X-ray analysis, the formazanate behaves as an anion or displays a mono- or bidentate coordination mode, for the Al, Fe or Cu centre, respectively. All complexes were tested as catalysts for the peroxidative (with H 2 O 2 ) oxidation of cyclohexane and cyclohexanol to the coresponding organic products at room temperature. The complexes 2 and 3 are active homogeneous catalysts for the microwave-assisted peroxidative oxidation with aqueous H 2 O 2 of cyclohexane (to cyclohexanol and cyclohexanone) and cyclohexanol to cyclohexanone. The synthesis, structure and catalytic performance of water-soluble Al( iii ), Fe( iii ) and Cu( ii ) formazanates in the oxidation of cyclohexane and cyclohexanol to the coresponding organic products are reported.
ISSN:1144-0546
1369-9261
DOI:10.1039/d1nj06211e