New binuclear complexes of La(III), Nd(III), Sm(III), Eu(III), Gd(III) and Tb(III) ions with mefenamic acid were obtained in solid phase. For all compounds considered, complexation occurs at pH 6–6.5. The analyzed complexes were characterized on the basis of chemical and elemental analyses, molar conductance, UV–Vis, IR and 1H NMR spectroscopies as well as thermoanalytical techniques. According to the research results, the molecular formula of the complexes is Ln₂(C₁₅H₁₄NO₂)₃(OH)₃×nH₂O, with the exception of the La(III) complex which has the formula La₂(C₁₅H₁₄NO₂)₅(OH). The results show that only the carboxyl group is involved in the coordination of the rare earth ions in the bidentate mode. Coordination does not occur through the nitrogen atom. All the complexes are soluble in DMSO, and they are nonelectrolytes. The TG-FTIR technique was employed in order to study a decomposition pathway of the obtained compounds. The received results provide information on the composition, thermal stability, thermal decomposition, as well as the gaseous products that evolved during the thermal decomposition of the considered compounds.

The acid–base chemistry of three zwitterionic compounds, namely anthranilic (2-aminobenzoic acid), N-methylanthranilic and N-phenylanthranilic acid has been characterized in terms of the macroconstants K _a1, K _a2, the isoelectric point pH _I, the tautomerization constant K _z and microconstants k ₁₁, k ₁₂, k ₂₁, k ₂₂. The potentiometric titration method was used to determine the macrodissociation constants. Due to the very poor water solubility of N-phenylanthranilic acid the dissociation constants pK _a1 and pK _a2 were determined in MDM–water mixtures [MDM is a co-solvent mixture, consisting of equal volumes of methanol (MeOH), dioxane and acetonitrile (MeCN)]. The Yasuda–Shedlovsky extrapolation procedure has been used to obtain the values of pK _a1 and pK _a2 in aqueous solutions. The pK _a1 and pK _a2 values obtained by this method are 2.86 ± 0.01 and 4.69 ± 0.03, respectively. The tautomerization constant K _z describing the equilibrium between unionized form ⇌ zwitterionic form was evaluated by the K _z method based on UV–VIS spectrometry. The method uses spectral differences between the zwitterionic form (found at isoelectric pH in aqueous solution) and the unionized form (formed in an organic solvent of low dielectric constant). The highest value of the K _z constant has been observed in the case of N-methylantranilic acid (log₁₀ K _z = 1.31 ± 0.04). The values of log₁₀ K _z for anthranilic and N-phenylanthranilic acids are similar and have values of 0.93 ± 0.03 and 0.90 ± 0.05, respectively. The results indicate that the tested compounds, in aqueous solution around the isoelectric point pH_I, occur mainly in the zwitterionic form. Moreover, the influence of the type of substituent and pH of the aqueous phase on the equilibrium were analyzed with regard to the formation and the coexistence of different forms of the acids in the examined systems.

In this paper, the flufenamic acid equilibria in aqueous solution and in two-phase organic solvent + aqueous solution are described and presented. The dissociation constants K _a1 and K _a2 were determined in MDM + water mixtures. The Yashuda-Shedlovsky extrapolation procedure has been used to obtain the values of K _a1 and K _a2 in aqueous solutions. The distribution ratio D was measured in the toluene + water system over a wide range of pH by the shaking flask method. Based on the results of potentiometric titrations in two-phase organic solvent (benzene, ethylbenzene, toluene, carbon tetrachloride, chloroform, chlorobenzene, and bromobenzene) + aqueous systems, and using models of single and multistep equilibria, the values of distribution constants K _D and dimerization constants K _dim were calculated. The influences of polarity of the applied solvents and pH of the aqueous phase, on the speciation of the particular forms of flufenamic acid in both phases, were demonstrated.

This study presents the synthesis and physicochemical characterization of coordination compounds formed between chrysin, a natural flavonoid, and transition metal ions: Mn(II), Co(II), and Zn(II). The complexes were obtained under mildly basic conditions and analyzed using elemental analysis, thermogravimetric analysis (TGA), silver-assisted laser desorption/ionization mass spectrometry (SALDI-MS), FT-IR spectroscopy, and ¹H NMR. The spectroscopic data confirm that chrysin coordinates as a bidentate ligand through the 5-hydroxyl and 4-carbonyl groups, with structural differences depending on the metal ion involved. The mass spectrometry results revealed distinct stoichiometries: 1:2 metal-to-ligand ratios for Mn(II) and Co(II), and 1:1 for Zn(II), with additional hydroxide coordination. Biological assays demonstrated that Co(II) and Mn(II) complexes exhibit enhanced antibacterial and anti-biofilm activity compared to free chrysin, particularly against drug-resistant Staphylococcus epidermidis, whereas the Zn(II) complex showed negligible biological activity.