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Mixed thioalkyl-azoimine (SNN′)/α-diimine–ruthenium complexes: synthesis, characterization, DFT calculations, crystal structure and application as pre-catalysts for hydrogenation of acetophenone

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Abstract

Eight ruthenium complexes having thioalkyl-azoimine (SNN) ligands of two general types have been synthesized: (a) [Ru(L)(bipy)Cl](PF6) where {bipy = bipyridine, L = (2-SR)C6H4N=NC(COCH3)=NC6H4X, R = Ph (X = H, L1, 1; X = CH3, L2, 2; X = F, L3, 3); R = Me, (X = H, L4, 4)} and (b) [Ru(L1)(N–N)Cl](PF6) {N–N = 4,4-dimethyl-2,2′-bipyridine (dmbipy) (5), (1,10-phenanthroline) phen (6), 3,4,7,8-tetramethyl-1,10-phenanthroline (tetrmphen) (7), 5-5-chloro-1,10-phenanthroline (Clphen) (8). The crystal structures for 1 and 6 as well as for L2 are reported; the crystal structures of 1 and 6 show that L1 is bound to the ruthenium center as κ3[S,N,N′]. The complexes have been characterized by IR, UV/Vis and NMR spectroscopy as well as electrochemical (CV) techniques. The effect of groups X, the substituent R and N–N bidentate ligands on the electronic properties of the resulting mononuclear ruthenium complexes was investigated. The catalytic activity of these complexes was tested in the liquid-phase hydrogenation of acetophenone.

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Acknowledgements

Financial support from the Scientific Research Support Fund (Bas/2/3/2014) and Hashemite University, Jordan, is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Hashemite University, P.O. Box 150459, Zarqa, 13115, Jordan

    Mousa Al-Noaimi

  2. Department of Chemistry, College of Science, King Faisal University, PO Box 400, Hofuf, 31982, Saudi Arabia

    Mousa Al-Noaimi

  3. Department of Chemistry, The University of Jordan, Amman, 11942, Jordan

    Firas F. Awwadi

  4. Department of Chemistry, Yarmouk University, P.O. Box 566, Irbid, Jordan

    Ayman Hammoudeh & Maha Tanash

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  1. Mousa Al-Noaimi
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  2. Firas F. Awwadi
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  3. Ayman Hammoudeh
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Al-Noaimi, M., Awwadi, F.F., Hammoudeh, A. et al. Mixed thioalkyl-azoimine (SNN′)/α-diimine–ruthenium complexes: synthesis, characterization, DFT calculations, crystal structure and application as pre-catalysts for hydrogenation of acetophenone. Transit Met Chem 44, 355–367 (2019). https://doi.org/10.1007/s11243-018-00302-2

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  • DOI: https://doi.org/10.1007/s11243-018-00302-2

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