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Synthesis and characterization of novel bis(diphenylphosphino)-oxalyl and (substituted) malonyl dihydrazones: P,N,N,P-tetradentate complexes of an oxalyl derivative with Cu(II), Pd(II), and Mn(II)

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Abstract

Novel ligands of bis(diphenylphosphino)-oxalyl, malonyl, and methyl- and ethyl-malonyl dihydrazones were synthesized by condensation of oxalyl, malonyl, methyl-malonyl, and ethyl-malonyl dihydrazide with o-(diphenylphosphino)benzaldehyde in different conditions. The dihydrazones exhibit three different tautomeric structures detected by NMR and IR spectra. The 31P NMR spectrum demonstrates four different singlet signals, i.e., chemical shifts, of the three respective tautomers. Complexes of the oxalyl ligand with Pd2+, Cu2+, and Mn2+ ions are formed in 1:1 molar ratio. Their structures were characterized by IR, NMR, EPR, MS, EA, and TGA, in which the oxalyl ligand acts as a neutral P,N,N,P-tetradentate chelate. The pH stability of the complexes is in the region of ca. 4.5–7.5 and their activation energy was calculated from the conductivity measurements.

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Acknowledgments

The authors greatly thank Prof. Dr. Rinaldo Poli, Laboratoire de Chimie de Coordination (LCC), UPR CNRS 8241 205, Route de Narbonne, 31077 Toulouse Cedex 4, France, for his continued and precious advice and encouragement to produce this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Sohag University, Sohâg, 82534, Egypt

    Mohamed Shaker S. Adam, Ahmad Desoky M. Mohamad & Omar M. El-Hady

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  1. Mohamed Shaker S. Adam
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  2. Ahmad Desoky M. Mohamad
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  3. Omar M. El-Hady
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Correspondence to Mohamed Shaker S. Adam.

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Adam, M.S.S., Mohamad, A.D.M. & El-Hady, O.M. Synthesis and characterization of novel bis(diphenylphosphino)-oxalyl and (substituted) malonyl dihydrazones: P,N,N,P-tetradentate complexes of an oxalyl derivative with Cu(II), Pd(II), and Mn(II). Monatsh Chem 145, 435–445 (2014). https://doi.org/10.1007/s00706-013-1122-4

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