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Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent

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Abstract
(2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide [C18H20NOPS (2)] is a novel oxime derivative that has been identified, in a recent work from our group, as a potential antibacterial agent. Herein, we report the in-depth structural analysis of compound (2) by using various spectroscopic tools including FT-IR, NMR (H-1, P-31, C-13), mass spectrometry and single crystal X-ray diffraction, which indicate that it is obtained as a mixture of Z and E isomers. The different mechanisms, inversion, rotation, or mixed inversion-rotation, by which could occur the Z/E isomerization, have been investigated computationally with DFT method. Total and frontier molecular orbitals energies for both isomers were derived in order to gain more insights into their relative stabilities and biological activities. In silico molecular docking studies in E. coli FabH enzyme active site were also performed to predict the possible interaction modes and binding energies for both Z and E isomers as compared with those of a reference FabH inhibitor. (C) 2020 Elsevier B.V. All rights reserved.
Keywords
Oximes, Phosphine sulfides, Z/E isomerism, X-ray diffraction, DFT calculations, In silico molecular docking, FabH inhibitors, Antibacterial activity, isomerisation

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MLA
Jebli, Nejib, et al. “Experimental and Computational Investigation of Z/E Isomerism, X-Ray Crystal Structure and Molecular Docking Study of (2-(Hydroxyimino)Cyclohexyl)Diphenylphosphine Sulfide, a Potential Antibacterial Agent.” JOURNAL OF MOLECULAR STRUCTURE, vol. 1229, 2021, doi:10.1016/j.molstruc.2020.129634.
APA
Jebli, N., Arfaoui, Y., Van Hecke, K., Cavalier, J.-F., & Touil, S. (2021). Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent. JOURNAL OF MOLECULAR STRUCTURE, 1229. https://doi.org/10.1016/j.molstruc.2020.129634
Chicago author-date
Jebli, Nejib, Youssef Arfaoui, Kristof Van Hecke, Jean-Francois Cavalier, and Soufiane Touil. 2021. “Experimental and Computational Investigation of Z/E Isomerism, X-Ray Crystal Structure and Molecular Docking Study of (2-(Hydroxyimino)Cyclohexyl)Diphenylphosphine Sulfide, a Potential Antibacterial Agent.” JOURNAL OF MOLECULAR STRUCTURE 1229. https://doi.org/10.1016/j.molstruc.2020.129634.
Chicago author-date (all authors)
Jebli, Nejib, Youssef Arfaoui, Kristof Van Hecke, Jean-Francois Cavalier, and Soufiane Touil. 2021. “Experimental and Computational Investigation of Z/E Isomerism, X-Ray Crystal Structure and Molecular Docking Study of (2-(Hydroxyimino)Cyclohexyl)Diphenylphosphine Sulfide, a Potential Antibacterial Agent.” JOURNAL OF MOLECULAR STRUCTURE 1229. doi:10.1016/j.molstruc.2020.129634.
Vancouver
1.
Jebli N, Arfaoui Y, Van Hecke K, Cavalier J-F, Touil S. Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent. JOURNAL OF MOLECULAR STRUCTURE. 2021;1229.
IEEE
[1]
N. Jebli, Y. Arfaoui, K. Van Hecke, J.-F. Cavalier, and S. Touil, “Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent,” JOURNAL OF MOLECULAR STRUCTURE, vol. 1229, 2021.
@article{8700750,
  abstract     = {{(2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide [C18H20NOPS (2)] is a novel oxime derivative that has been identified, in a recent work from our group, as a potential antibacterial agent. Herein, we report the in-depth structural analysis of compound (2) by using various spectroscopic tools including FT-IR, NMR (H-1, P-31, C-13), mass spectrometry and single crystal X-ray diffraction, which indicate that it is obtained as a mixture of Z and E isomers. The different mechanisms, inversion, rotation, or mixed inversion-rotation, by which could occur the Z/E isomerization, have been investigated computationally with DFT method. Total and frontier molecular orbitals energies for both isomers were derived in order to gain more insights into their relative stabilities and biological activities. In silico molecular docking studies in E. coli FabH enzyme active site were also performed to predict the possible interaction modes and binding energies for both Z and E isomers as compared with those of a reference FabH inhibitor. (C) 2020 Elsevier B.V. All rights reserved.}},
  articleno    = {{129634}},
  author       = {{Jebli, Nejib and Arfaoui, Youssef and Van Hecke, Kristof and Cavalier, Jean-Francois and Touil, Soufiane}},
  issn         = {{0022-2860}},
  journal      = {{JOURNAL OF MOLECULAR STRUCTURE}},
  keywords     = {{Oximes,Phosphine sulfides,Z/E isomerism,X-ray diffraction,DFT calculations,In silico molecular docking,FabH inhibitors,Antibacterial activity,isomerisation}},
  language     = {{eng}},
  pages        = {{11}},
  title        = {{Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent}},
  url          = {{http://doi.org/10.1016/j.molstruc.2020.129634}},
  volume       = {{1229}},
  year         = {{2021}},
}

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