Structural and thermal properties of three cyano-substituted azoderivatives of β-diketones
2011
Mahmudov, Kamran T. | Kopylovich, Maximilian N. | Luzyanin, Konstantin V. | Mizar, Archana | Guedes da Silva, M. Fátima C. | André, Vânia | Pombeiro, Armando J.L.
3-(2-Cyanophenylhydrazo)pentane-2,4-dione (HL¹), 3-(4-cyanophenylhydrazo)pentane-2,4-dione (HL²) and 1-ethoxy-2-(4-cyanophenylhydrazo)butane-1,3-dione (HL³), and the Pd(II) complex [Pd(L²)₂] were synthesized and characterized by IR, ¹H and ¹³C NMR spectroscopies, ESI-MS, elemental and X-ray diffraction analyses (for HL¹). HL³ derived from the unsymmetric 1-ethoxybutane-1,3-dione exists in solution as a mixture of the enol-azo and hydrazo tautomeric forms and a decrease of the solvent polarity shifts the tautomeric balance to the hydrazo form, while for HL¹ and HL², derived from the symmetric pentane-2,4-dione, the hydrazo form is dominating under all the studied conditions. HL¹–³ and [Pd(L²)₂] show a high thermal stability with well-defined peaks of phase transition at 438 (HL¹), 462 (HL²), 392 (HL³) and 404K ([Pd(L²)₂]).
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