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A Hydrazone Derivative: Synthesis, Crystal Structure, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis and Computational Study

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Abstract

The diazotization reaction of o-trifluoromethyl aniline from aromatic amines with 5,5-dimethylcyclohexane-1,3-dione was studied, as a result, 2-(2-(o-trifluoromethylphenyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione (THDCD) was synthesized and its structure was confirmed by X-ray diffraction analysis. The solid state assembly is stabilized by numerous intermolecular interactions which are deeply probed by Hirshfeld surface analysis. The enrichment ratio was computed for getting the contact with the highest propensity to form crystal packing interaction. The mechanical response of the crystal is predicted by voids analysis. Moreover, interaction energy calculations were performed at HF/3-21G electron density model to further inspect the supramolecular assembly of the crystal. DFT calculation was conducted using B3LYP level with 6-311++G(d,p) basic set with the help of Gaussian09W and GaussView 6.0 packages. MEP surface, HOMO–LUMO orbitals, and NBO theory were analyzed via DFT approach. Theoretical method confirms the proposed geometry of THDCD by X-ray analysis.

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Authors and Affiliations

  1. Baku State University, Organic Chemistry Department, Baku, Republic of Azerbaijan

    M. Kurbanova, A. Sadigova & A. Maharramov

  2. Department of Physics, University of Sargodha, Sargodha, Pakistan

    M. Ashfaq & M. N. Tahir

  3. Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran

    M. Feizi-Dehnayebi

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  1. M. Kurbanova
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Text © The Author(s), 2024, published in Zhurnal Strukturnoi Khimii, 2024, Vol. 65, No. 1, 120562.https://doi.org/10.26902/JSC_id120562

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Kurbanova, M., Ashfaq, M., Sadigova, A. et al. A Hydrazone Derivative: Synthesis, Crystal Structure, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis and Computational Study. J Struct Chem 65, 92–106 (2024). https://doi.org/10.1134/S0022476624010098

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