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Synthesis, spectroscopic characterization, crystal structure and theoretical investigation of two azo-palladium (II) complexes derived from substituted (1-phenylazo)-2-naphtol

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Abstract

The ortho-substituted (E)-1-((2-methoxyphenyl)diazenyl)naphthalen-2-ol and the meta-substituted (E)-1-((3-methoxyphenyl)diazenyl)naphthalen-2-ol were, respectively, used in the synthesis of two new complexes, bis[1-(2-methoxyphenylazo)-2-naphthoxy]palladium(II) and bis[1-(3-methoxyphenylazo)-2-naphthoxy]palladium(II), noted (I) and (II), respectively. (I) and (II) were characterized by physicochemical and spectroscopic methods, and their molecular structures were determined by X-ray crystallography. Both complexes display a square-planar geometry, which is reproduced by full geometry optimizations at the DFT/B3LYP level. Calculations were also performed on the free ligands (in their precursor form), as well as their para-substituted isomer (E)-1-((4-methoxyphenyl)diazenyl)naphthalen-2-ol and its hypothetical complex bis[1-(4-methoxyphenylazo)-2-naphthoxy]palladium(II) (compound (III). Calculations were also performed on the free p-phenylazo-2-naphthol ligand (p-MoxyPhNap), in order to understand their bonding and to analyze their electronic structure. TD-DFT calculations were also performed on the three complexes to simulate their absorption spectra from and compare to the experimental UV–Vis data of (I) and (II). The main peaks in the spectrum of (I) are assigned to mixed LMCT/LLCT and π–π * (ILCT) transition, while the unique major peak afforded by (II) is assigned to MLCT and LLCT transitions.

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Funding

The authors received financial support from the Algerian MESRS (Ministère de l’Enseignement Supérieur et de la RechercheScientifique) and DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique).

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Authors and Affiliations

  1. Unité de Recherche de Chimie de L’Environnement Et Moléculaire Structurale, Université Constantine Mentouri, 25000, Constantine, Algeria

    Souheila Chetioui, Bachir Zouchoune, Hocine Merazig, Salah-Eddine Bouaoud & DjamilAzeddine Rouag

  2. Laboratoire de Chimie appliquée Et Technologie Des Matériaux, Université Larbi Ben M’Hidi - Oum El Bouaghi, 04000, Oum El Bouaghi, Algeria

    Bachir Zouchoune & Salah-Eddine Bouaoud

  3. Université Mohamed Boudiaf-M’Sila, M’Sila, Algérie

    Souheila Chetioui

  4. Laboratoire de Chimie Et Systémique Organométallique(LCSOM), Institut de Chimie, Université de Strasbourg, UMR 7177, 67070, Strasbourg Cedex, France

    Jean-Pierre Djukic

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  1. Souheila Chetioui
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  2. Bachir Zouchoune
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  3. Hocine Merazig
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  4. Salah-Eddine Bouaoud
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  5. DjamilAzeddine Rouag
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The manuscript was written through contribution of all authors. All authors have given approval to the final version of the manuscript.

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Correspondence to Bachir Zouchoune.

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This paper is dedicated to Dr. Jean-René Hamon at the occasion of his 65th birthday.

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Chetioui, S., Zouchoune, B., Merazig, H. et al. Synthesis, spectroscopic characterization, crystal structure and theoretical investigation of two azo-palladium (II) complexes derived from substituted (1-phenylazo)-2-naphtol. Transit Met Chem 46, 91–101 (2021). https://doi.org/10.1007/s11243-020-00425-5

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