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Synthesis, Crystal Structure, DFT Calculations and Hirshfeld Surface Analysis of 3-Chloro-2,6-Bis(4-Chlorophenyl)-3-Methylpiperidin-4-One

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Abstract

The 3-chloro-2,6-bis(4-chlorophenyl)-3-methylpiperidin-4-one (CCMP) compound have been characterized by FT-IR, 1H-NMR, 13C-NMR, 1H-1H NOESY spectroscopy and single-crystal X-ray diffraction. The title compound crystallizes in the orthorhombic space group Pna21. The single crystal measurements reveal a distorted chair conformation [puckering parameter Q = 0.557 (3) A°; θ = 167.8 (3)° and Ψ = 206.8 (13)°]. The optimized geometric parameters and frequency values were theoretically calculated using DFT/B3LYP method with B3LYP/6–31+G(d,p) basis set. The XRD single crystal measurement parameters are good agreed with the optimized parameters. The spectral and optimized parameters showed that the piperidine-4-one ring adopts normal chair conformation with equatorial orientations of all the substituents except chlorine. The frontier molecular orbitals HOMO and LUMO were computed to know the chemical reactivity and kinetic stability of the molecular compound. Hirshfeld surface analysis was also performed. Hirshfeld surface analysis (dnorm surface, two-dimensional fingerprint plots and molecular electrostatic potantials) revealed the nature of intermolecular interactions. The most important contributions for the crystal packing are from H···H (35%), Cl···H/H···Cl (32.3%), C···H/H···C (15%) and O···H/H···O (7.5%) interactions.

Graphic Abstract

In this study, spectroscopic properties of a new piperidine-4-one crystal compound and it’s DFT structural investigation compared with experimental were gained to literature.

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Authors and Affiliations

  1. Department of Electrical and Computer Engineering, National University of Singapore, Lower Kent Ridge, 117583, Singapore

    Arulraj Ramalingam

  2. Department of Fundamental Sciences, Faculty of Engineering, Samsun University, Samsun, 55420, Turkey

    Sevgi Kansız

  3. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Necmi Dege

  4. Research and Development Centre, Bharathiar University, Coimbatore, 641 046, Tamil Nadu, India

    Sivakumar Sambandam

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  1. Arulraj Ramalingam
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  2. Sevgi Kansız
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  3. Necmi Dege
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  4. Sivakumar Sambandam
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Correspondence to Arulraj Ramalingam or Sevgi Kansız.

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Ramalingam, A., Kansız, S., Dege, N. et al. Synthesis, Crystal Structure, DFT Calculations and Hirshfeld Surface Analysis of 3-Chloro-2,6-Bis(4-Chlorophenyl)-3-Methylpiperidin-4-One. J Chem Crystallogr 51, 273–287 (2021). https://doi.org/10.1007/s10870-020-00852-3

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