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A combined experimental and theoretical approach for structural study on a new cinnamoyl derivative of 2-acetyl-1,3-indandione and its metal(II) complexes

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Abstract

The synthesis, structure and spectral properties of a new cinnamoyl derivative of 2-acetyl-1,3-indandione (2AID), p-fluoro-cinnamoyl-1,3-indandione, LH and its metal(II) complexes with Cu(II), Zn(II) and Cd(II), are described. In order to verify the molecular structure of the free ligand and its metal complexes, model geometries based on the spectroscopic data were optimized using quantum chemical methods. The experimental spectroscopic data (IR and NMR) of the ligand, LH, complemented by the calculated ones, show that it exists in the exocyclic enolic form in the gas phase, solution and solid state. Good quality single crystals of Cd(II) complex were obtained from a DMSO solution and were studied by means of single-crystal X-ray diffraction. The data show bidentate coordination of the ligand and two DMSO molecules coordinated to the metal centre, thus forming a complex with octahedral geometry. On the contrary, the spectroscopic data on the amorphous samples indicate a square planar geometry of the Cu(II) complex and distorted octahedral geometry for Zn(II) and Cd(II) complexes with two water molecules coordinated to the metal centre. The used quantum chemical method for structure optimization of the transition metal complexes, B3LYP/LANL2DZ, shows very good agreement with the crystallographic data and, therefore, was also employed for structural determination for the non-crystalline complexes.

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Acknowledgement

This work has been supported by the Bulgarian National Science Fund, Contract MYX-1502/05.

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Authors and Affiliations

  1. Faculty of Chemistry, University of Sofia, 1, J. Bourchier av, 1164, Sofia, Bulgaria

    Anife Ahmedova & Mariana Mitewa

  2. Faculty of Chemistry, University of Plovdiv, 24, Tzar Assen street, 4000, Plovdiv, Bulgaria

    Petja Marinova

  3. Dipartimento di Chimica, Università degli Studi di Firenze, Via della Lastruccia 3, I-50019, Sesto Fiorentino (FI), Italy

    Samuele Ciattini

  4. Rousse University, Technological Branch—Razgrad, 3, Aprilsko vastanie str, Razgrad, 7200, Bulgaria

    Neyko Stoyanov

  5. Department of Physical and Theoretical Chemistry, University of Saarland, 66123, Saarbruecken, Germany

    Michael Springborg

Authors
  1. Anife Ahmedova
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  2. Petja Marinova
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  3. Samuele Ciattini
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  4. Neyko Stoyanov
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  5. Michael Springborg
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  6. Mariana Mitewa
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Corresponding author

Correspondence to Anife Ahmedova.

Electronic supplementary material

Below is the link to the electronic supplementary material.

11224_2008_9393_MOESM1_ESM.doc

MOESM1 [Supplementary material—S1. Experimental and calculated 13C-NMR shifts for b isomer, with GIAO-B3LYP method and various basis sets, in ppm relative to TMS*. For atoms numbering, see Fig. 1.] (DOC 41 kb)

11224_2008_9393_MOESM2_ESM.doc

MOESM2 [Supplementary material—S2. Experimental and calculated 13C-NMR shifts for acis isomer, with GIAO-B3LYP method and various basis sets, in ppm relative to TMS*. For atoms numbering, see Fig. 1.] (DOC 43 kb)

MOESM3 (DOC 21 kb)

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Ahmedova, A., Marinova, P., Ciattini, S. et al. A combined experimental and theoretical approach for structural study on a new cinnamoyl derivative of 2-acetyl-1,3-indandione and its metal(II) complexes. Struct Chem 20, 101–111 (2009). https://doi.org/10.1007/s11224-008-9393-9

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  • DOI: https://doi.org/10.1007/s11224-008-9393-9

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