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Title: Synthesis, Crystal Structure, DFT Calculations and Hirshfeld Surface Analysis of 3-Chloro-2,6-Bis(4- Chlorophenyl)-3-Methylpiperidin-4-One
Authors: Arulraj Ramalingam 
Sevgi Kansız
Necmi Dege
Sivakumar Sambandam
Keywords: Piperidin-4-one · DFT · HOMO-LUMO · MEP · Hirshfeld surface analysis · DFT/B3LYP/6-31+G(d,p)
Issue Date: 13-Aug-2020
Publisher: Journal of Chemical Crystallography
Citation: Arulraj Ramalingam, Sevgi Kansız, Necmi Dege, Sivakumar Sambandam (2020-08-13). Synthesis, Crystal Structure, DFT Calculations and Hirshfeld Surface Analysis of 3-Chloro-2,6-Bis(4- Chlorophenyl)-3-Methylpiperidin-4-One. ScholarBank@NUS Repository.
Rights: CC0 1.0 Universal
Abstract: The 3-chloro-2,6-bis(4-chlorophenyl)-3-methylpiperidin-4-one (CCMP) compound have been characterized by FT-IR, 1HNMR, 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.
DOI: 10.1007/s10870-020-00852-3
Rights: CC0 1.0 Universal
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