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Binuclear and polymeric Hg(II) complexes of an ambidentate phosphorus ylide : synthesis, crystal structure, antibacterial activity, and theoretical studies

Seyyed Javad Sabounchei, Faeze Kazemi Andalib, Marjan Hosseinzadeh, Asieh Sedghi, Ali Hashemi, Roya Karamian and Kristof Van Hecke (UGent)
(2019) APPLIED ORGANOMETALLIC CHEMISTRY. 34(1).
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Abstract
The new alpha-keto-stabilized phosphorus ylide Ph3PCHC(O)PhCN (Y) was synthesized by addition of triphenylphosphine to 2-bromo-4 '-cyanoacetophenone, followed by treatment with NaOH 10%. Reaction of ligand (Y) with methanolic solution of mercury(II) halides under mild conditions yielded the binuclear complexes [Y center dot HgX2](2) [X=Cl (1), Br (2), I (3)]. The new organic/inorganic composite polymer [Hg(NO3)(2)(Y)](n) (4) was synthesized by the reaction of mercury(II) nitrate with the phosphorus ylide Y. Compounds synthesized were characterized by Fourier-transform infrared, H-1, P-31, and C-13 nuclear magnetic resonance spectroscopic methods, which confirmed the coordination of ylide to the metal center through the ylidic carbon atom. Single-crystal X-ray structures of phosphorus ylide Y and polymeric complex 4 were also determined and the crystallographic data of complex 4 showed that the title complex has an infinite one-dimensional structure. Furthermore, the electronic and molecular structures of complexes 1-3 were investigated at the BP86/def2-SVP level of theory, indicating an increasing trend for C -> M bond lengths: Hg2I2 > Hg2Br2 > Hg2Cl2 in [Y -> HgX2](2) (X = Cl, Br, I) complexes. In addition, the antibacterial activity of ligand Y and all complexes using the agar disc diffusion method was examined against both selected gram-positive and gram-negative bacteria. Results indicated that the ligand Y and complexes 1 and 4 show good antibacterial effect against gram-positive bacteria tested; besides, the inhibition zones of complexes were significantly larger than those of chloramphenicol as standard.
Keywords
X-RAY-STRUCTURE, MERCURY(II) COMPLEXES, BIFUNCTIONALIZED YLIDES, PALLADIUM(II) COMPLEXES, SULFONIUM YLIDES, HALIDE-COMPLEXES, ESSENTIAL OILS, COORDINATION, BENZOYLMETHYLENETRIPHENYLPHOSPHORANE, APPROXIMATION, antibacterial activity, crystal structure, phosphorus ylide, spectroscopic characterization, theoretical studies

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Citation

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MLA
Sabounchei, Seyyed Javad, et al. “Binuclear and Polymeric Hg(II) Complexes of an Ambidentate Phosphorus Ylide : Synthesis, Crystal Structure, Antibacterial Activity, and Theoretical Studies.” APPLIED ORGANOMETALLIC CHEMISTRY, vol. 34, no. 1, 2019.
APA
Sabounchei, S. J., Andalib, F. K., Hosseinzadeh, M., Sedghi, A., Hashemi, A., Karamian, R., & Van Hecke, K. (2019). Binuclear and polymeric Hg(II) complexes of an ambidentate phosphorus ylide : synthesis, crystal structure, antibacterial activity, and theoretical studies. APPLIED ORGANOMETALLIC CHEMISTRY, 34(1).
Chicago author-date
Sabounchei, Seyyed Javad, Faeze Kazemi Andalib, Marjan Hosseinzadeh, Asieh Sedghi, Ali Hashemi, Roya Karamian, and Kristof Van Hecke. 2019. “Binuclear and Polymeric Hg(II) Complexes of an Ambidentate Phosphorus Ylide : Synthesis, Crystal Structure, Antibacterial Activity, and Theoretical Studies.” APPLIED ORGANOMETALLIC CHEMISTRY 34 (1).
Chicago author-date (all authors)
Sabounchei, Seyyed Javad, Faeze Kazemi Andalib, Marjan Hosseinzadeh, Asieh Sedghi, Ali Hashemi, Roya Karamian, and Kristof Van Hecke. 2019. “Binuclear and Polymeric Hg(II) Complexes of an Ambidentate Phosphorus Ylide : Synthesis, Crystal Structure, Antibacterial Activity, and Theoretical Studies.” APPLIED ORGANOMETALLIC CHEMISTRY 34 (1).
Vancouver
1.
Sabounchei SJ, Andalib FK, Hosseinzadeh M, Sedghi A, Hashemi A, Karamian R, et al. Binuclear and polymeric Hg(II) complexes of an ambidentate phosphorus ylide : synthesis, crystal structure, antibacterial activity, and theoretical studies. APPLIED ORGANOMETALLIC CHEMISTRY. 2019;34(1).
IEEE
[1]
S. J. Sabounchei et al., “Binuclear and polymeric Hg(II) complexes of an ambidentate phosphorus ylide : synthesis, crystal structure, antibacterial activity, and theoretical studies,” APPLIED ORGANOMETALLIC CHEMISTRY, vol. 34, no. 1, 2019.
@article{8645671,
  abstract     = {The new alpha-keto-stabilized phosphorus ylide Ph3PCHC(O)PhCN (Y) was synthesized by addition of triphenylphosphine to 2-bromo-4 '-cyanoacetophenone, followed by treatment with NaOH 10%. Reaction of ligand (Y) with methanolic solution of mercury(II) halides under mild conditions yielded the binuclear complexes [Y center dot HgX2](2) [X=Cl (1), Br (2), I (3)]. The new organic/inorganic composite polymer [Hg(NO3)(2)(Y)](n) (4) was synthesized by the reaction of mercury(II) nitrate with the phosphorus ylide Y. Compounds synthesized were characterized by Fourier-transform infrared, H-1, P-31, and C-13 nuclear magnetic resonance spectroscopic methods, which confirmed the coordination of ylide to the metal center through the ylidic carbon atom. Single-crystal X-ray structures of phosphorus ylide Y and polymeric complex 4 were also determined and the crystallographic data of complex 4 showed that the title complex has an infinite one-dimensional structure. Furthermore, the electronic and molecular structures of complexes 1-3 were investigated at the BP86/def2-SVP level of theory, indicating an increasing trend for C -> M bond lengths: Hg2I2 > Hg2Br2 > Hg2Cl2 in [Y -> HgX2](2) (X = Cl, Br, I) complexes. In addition, the antibacterial activity of ligand Y and all complexes using the agar disc diffusion method was examined against both selected gram-positive and gram-negative bacteria. Results indicated that the ligand Y and complexes 1 and 4 show good antibacterial effect against gram-positive bacteria tested; besides, the inhibition zones of complexes were significantly larger than those of chloramphenicol as standard.},
  articleno    = {e5265},
  author       = {Sabounchei, Seyyed Javad and Andalib, Faeze Kazemi and Hosseinzadeh, Marjan and Sedghi, Asieh and Hashemi, Ali and Karamian, Roya and Van Hecke, Kristof},
  issn         = {0268-2605},
  journal      = {APPLIED ORGANOMETALLIC CHEMISTRY},
  keywords     = {X-RAY-STRUCTURE,MERCURY(II) COMPLEXES,BIFUNCTIONALIZED YLIDES,PALLADIUM(II) COMPLEXES,SULFONIUM YLIDES,HALIDE-COMPLEXES,ESSENTIAL OILS,COORDINATION,BENZOYLMETHYLENETRIPHENYLPHOSPHORANE,APPROXIMATION,antibacterial activity,crystal structure,phosphorus ylide,spectroscopic characterization,theoretical studies},
  language     = {eng},
  number       = {1},
  pages        = {13},
  title        = {Binuclear and polymeric Hg(II) complexes of an ambidentate phosphorus ylide : synthesis, crystal structure, antibacterial activity, and theoretical studies},
  url          = {http://dx.doi.org/10.1002/aoc.5265},
  volume       = {34},
  year         = {2019},
}
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