ABSTRACT
The synthesis and characterization of five metal complexes derived from sodium meclofenamate (1) are reported: [Cd(C14H10NO2Cl2)2â(CH3OH)]nânCH3OH (6), [Pb(C14H10NO2Cl2)2]n (7), [Co(C14H10NO2Cl2)]n (8), [Cu(C14H10NO2Cl2)]n (9), and [Cu(C14H10NO2Cl2)2(C5H5N)2] (10) (C14H10NO2Cl2=meclofenamate; C5H5N=pyridine). The characterization of the compounds was based on FTIR and UV-visible spectroscopy, mass spectrometry and, in the case of complexes 6 and 10, single crystal X-ray diffraction analysis. For compound 6, the structural analysis revealed a 1-D polymeric chain structure, in which pentagonal planar [Cd(RCOO)2(CH3OH)] units were linked through bridging carboxylate functions of the meclofenamate ligands. The overall coordination environment of the Cd(II) ions was seven-coordinate, since each carboxylate group exhibited a µ3-bridging coordination mode. On the other hand, for complex 10 a discrete mononuclear structure was observed, in which the six-coordinate copper(II) metal atoms were coordinated by two pyridine molecules and the carboxylate functions of two meclofenamate entities, in an anisobidentate coordination mode. The antibacterial activity of compounds 6-9 against four strains of Gram positive (Staphylococcus aureus and Bacillus subtilis) and Gram negative (Escherichia coli and Pseudomonas aeruginosa) bacteria was examined, finding that only complex 6 was active. Additionally, it was found that the Co(II) and Cu(II) complexes 8 and 9 showed peroxidase activity.
Subject(s)
Anti-Bacterial Agents/chemistry , Coordination Complexes/chemistry , Meclofenamic Acid/analogs & derivatives , Meclofenamic Acid/chemistry , Anti-Bacterial Agents/pharmacology , Bacillus subtilis/drug effects , Cadmium/chemistry , Cobalt/chemistry , Coordination Complexes/pharmacology , Copper/chemistry , Crystallography, X-Ray , Escherichia coli/drug effects , Hydrogen Bonding , Hydrogen Peroxide/chemistry , Lead/chemistry , Microbial Sensitivity Tests , Models, Molecular , Molecular Conformation , Pseudomonas aeruginosa/drug effects , Staphylococcus aureus/drug effectsABSTRACT
Arylboronic acids and different salen ligands have been brought to reaction in a 2:1 stoichiometry in ethanol, toluene, and acetonitrile. In all cases bimetallic boronates with chiral boron atoms could be isolated with the difference that in ethanol mostly open bimetallic boronic esters are obtained, while in toluene or acetonitrile closed bimetallic complexes with a central seven- or eight-membered heterocyclic ring are formed. Both structural types have been characterized by spectroscopic techniques and X-ray crystallography showing that the reactions are diastereoselective in the case of the bimetallic heterocyclic structures. The configurations and conformations of the seven- and eight-membered rings are different, and this may depend on steric effects and/or repulsive intramolecular pi-pi interactions between the two salicylidene moieties attached to the central ring.
