Theoretical and experimental study of triphenylphosphonium Schiff base of 5-hydroxy-3-methyl-1-phenyl-4-formylpyrazole |
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| Authors: | Sergey A Borodkin Leonid D Popov Milica R Milenkovi? Igor N Shcherbakov Vladimir V Lukov |
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| Institution: | 1. Chemistry Department, Southern Federal University, Rostov-on-Don, Russia;2. Faculty of Chemistry, University of Belgrade, Belgrade, Serbia |
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| Abstract: | 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. |
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| Keywords: | phosphonium salts quantum-chemical calculations schiff base tautomerism |
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