Theoretical and experimental study of triphenylphosphonium Schiff base of 5-hydroxy-3-methyl-1-phenyl-4-formylpyrazole

The Schiff base (HLBr), containing a chelating unit and triphenylphosphonium moiety has been synthesized in the reaction of 4-aminobenzyl(triphenyl)phosphonium bromide with 5-hydroxy-3-methyl-1-phenyl-4-formylpyrazole. The composition and structure of HLBr have been determined by elemental analysis,...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2018-06, Vol.193 (6), p.375-381
Main Authors: Borodkin, Sergey A., Popov, Leonid D., Tsaturyan, Arshak A., Milenković, Milica R., Shcherbakov, Igor N., Lukov, Vladimir V.
Format: Article
Language:English
Subjects:
Chelation
Chemical synthesis
Density functional theory
Imines
Infrared spectroscopy
Mass spectrometry
NMR
Nuclear magnetic resonance
Reaction mechanisms
Two dimensional analysis
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Summary:The Schiff base (HLBr), containing a chelating unit and triphenylphosphonium moiety has been synthesized in the reaction of 4-aminobenzyl(triphenyl)phosphonium bromide with 5-hydroxy-3-methyl-1-phenyl-4-formylpyrazole. The composition and structure of HLBr have been determined by elemental analysis, IR, 1D and 2D NMR, electronic spectroscopy and mass spectrometry. Density functional theory (DFT) calculations (6-311G(d,p) level of theory) have been carried out to investigate tautomeric forms of HL+ and the reaction mechanism of its formation and spectral properties. The most stable form in the solid state and in DMSO solution is pyrazolone (keto-amine) tautomeric form.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426507.2018.1424159