Synthesis, Crystal Structure, DFT Calculations and Hirshfeld Surface Analysis of 3-Chloro-2,6-Bis(4-Chlorophenyl)-3-Meth
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ORIGINAL PAPER
Synthesis, Crystal Structure, DFT Calculations and Hirshfeld Surface Analysis of 3‑Chloro‑2,6‑Bis(4‑Chlorophenyl)‑3‑Methylpiperidin‑4‑One Arulraj Ramalingam1 · Sevgi Kansız2 · Necmi Dege3 · Sivakumar Sambandam4 Received: 23 September 2019 / Accepted: 27 July 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
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 (d norm 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.
* Arulraj Ramalingam [email protected] * Sevgi Kansız [email protected] 1
Department of Electrical and Computer Engineering, National University of Singapore, Lower Kent Ridge 117583, Singapore
2
Department of Fundamental Sciences, Faculty of Engineering, Samsun University, Samsun 55420, Turkey
3
Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
4
Research and Development Centre, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India
13
Vol.:(0123456789)
Journal of Chemical Crystallography
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.
Keywords Piperidin-4-one · DFT · HOMO-LUMO · MEP · Hirshfeld surface analysis · DFT/B3LYP/6-31+G(d,p)
Introduction Piperidin-4-one constitutes an excellent class of structural motifs which have been found widely present in biologically active molecules [1]. The compounds of this family exhibit a broad spectrum of pharmacological properties such as antitumor, antibacterial, antiviral, antimalarial and antiprotozoal activities [2–4]. Furthermore, this type of compound with their huge potential in non- linear optical fields [4, 5] has drawn the concentration of photoscientists. 2,6 posit
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