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Crystallographic and computational study of the structure of copper(II) 2,2′-bis(2-oxidobenzylideneamino)-4,4′-dimethyl-1,1′-biphenyl

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Abstract

The reaction of M(OAc)2 with 2,2′-bis(2-hydroxybenzylideneamino)-4,4′-dimethyl-1,1′-biphenyl (H2L1) allows the synthesis of 2,2′-bis(2-oxidobenzylideneamino)-4,4′-dimethyl-1,1′-biphenyl complexes of Cu(II) (CuL1), Co(II) (CoL1) and Ni(II) (NiL1) that were characterized by elemental analysis, FTIR spectroscopy and for CuL1 also by X-ray crystallography verifying a tetradentate binding mode of L1 via an (ONNO) motif of the two phenolic oxygen atoms and two azomethine nitrogen atoms. Recrystallization from a solvent mixture of dichloromethane and methanol promotes the formation of methanol adducts. Different binding modes of the methanol–complex were investigated using density functional theory calculations and binding energies, and thermodynamic data of the interaction are reported. The results show that the favored interaction occurs when the methanol molecule acts as a Lewis acid weakly binding via an O–H···O hydrogen bridge to a phenoxide moiety leading to an elongation of the respective M–O bond.

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Acknowledgements

We acknowledge the valuable support of the NMR (www.nmr.uni-jena.de) and mass spectrometry service platforms (www.ms.uni-jena.de) of the Faculty of Chemistry and Earth Sciences of the Friedrich Schiller University Jena, Germany.

Funding

We highly appreciate the generous financial support of the Project We1561/21 by the German Research Foundation (DFG, Bonn, Germany).

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Authors and Affiliations

  1. Department of Chemistry and Chemical Technology, Tafila Technical University (TTU), P. O. Box 179, Tafila, 66110, Jordan

    Taher S. Ababneh & Tareq M. A. Al-Shboul

  2. Department of Chemistry, Yarmouk University, Irbid, 21163, Jordan

    Taghreed M. A. Jazzazi

  3. Department of Chemistry, University of Petra, Amman, 11196, Jordan

    Mohammed I. Alomari

  4. Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University Jena (FSU), Humboldtstraße 8, 07743, Jena, Germany

    Helmar Görls & Matthias Westerhausen

Authors
  1. Taher S. Ababneh
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  2. Tareq M. A. Al-Shboul
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  3. Taghreed M. A. Jazzazi
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  4. Mohammed I. Alomari
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  5. Helmar Görls
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  6. Matthias Westerhausen
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Correspondence to Taher S. Ababneh.

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Ababneh, T.S., Al-Shboul, T.M.A., Jazzazi, T.M.A. et al. Crystallographic and computational study of the structure of copper(II) 2,2′-bis(2-oxidobenzylideneamino)-4,4′-dimethyl-1,1′-biphenyl. Transit Met Chem 45, 435–442 (2020). https://doi.org/10.1007/s11243-020-00395-8

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  • DOI: https://doi.org/10.1007/s11243-020-00395-8

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