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Binuclear and polymeric Hg(II) complexes of an ambidentate phosphorus ylide: Synthesis, crystal structure, antibacterial activity, and theoretical studies
Author(s) -
Sabounchei Seyyed Javad,
Kazemi Andalib Faeze,
Hosseinzadeh Marjan,
Sedghi Asieh,
Hashemi Ali,
Karamian Roya,
Van Hecke Kristof
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5265
Subject(s) - ylide , chemistry , triphenylphosphine , ligand (biochemistry) , crystal structure , medicinal chemistry , inorganic chemistry , stereochemistry , nuclear chemistry , crystallography , organic chemistry , catalysis , biochemistry , receptor
The new α‐keto‐stabilized phosphorus ylide Ph 3 PCHC(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·HgX 2 ] 2 [X=Cl ( 1 ), Br ( 2 ), I ( 3 )]. The new organic/inorganic composite polymer [Hg(NO 3 ) 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, 1 H, 31 P, and 13 C 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: Hg 2 I 2 > Hg 2 Br 2 > Hg 2 Cl 2 in [Y→HgX 2 ] 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.