Relationship between solid state structure and solution stability of copper(II)–hydroxypyridinecarboxylate complexes
Nóra V. May,G. Tamás Gál,Zsolt Szentendrei,László Korecz,Zoltán May,Maria Grazia Ferlin,Annalisa Dean,Petra Bombicz,Valerio Di Marco +8 more
TL;DR: In this article, a series of bioactive ligands 3-hydroxy-1-methyl-4-pyridinecarboxylate with copper(II) have been investigated and the bidentate coordination mode of the ligands has been found preferentially with cis arrangements in 1 and 2 and trans arrangements in 3-5.
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Abstract: The complementary solid state/solution studies of the systematic series of bioactive ligands 3-hydroxy-1-methyl-4-pyridinecarboxylate (L1), 3-hydroxy-1,2,6-trimethyl-4-pyridinecarboxylate (L2), 4-hydroxy-1-methyl-3-pyridinecarboxylate (L3), 4-hydroxy-1,6-dimethyl-3-pyridinecarboxylate (L4), 4-hydroxy-1-(2-hydroxyethyl)-6-methyl-3-pyridinecarboxylate (L5) and 4-hydroxy-1-(2-carboxyethyl)-6-methyl-3-pyridinecarboxylate (L6) with copper(II) have been performed in order to design efficient chelating drugs for the treatment of metal overloading conditions. Single crystals of [Cu(L1)2(H2O)]·3H2O (1) (monomer) with axial water coordination, [Cu2(L2)4]·6H2O (2) and [Cu2(L3)4]·4H2O (3) (cyclic dimers), where pyridinolato and carboxylato oxygens, respectively, act as linkers between adjacent copper complexes, [Cu(L4)2]n·3H2O (4) (1D polymer) and [Cu3(L5)6]·18H2O (5) (trimer), constructed using two square-pyramidal and one elongated octahedral Cu(II) complexes have been determined by SXRD. The bidentate coordination mode of the ligands has been found preferentially with cis arrangements in 1 and 2 and trans arrangements in 3–5. The solution speciation and complex stability of aqueous solutions have been studied by pH-dependent electron paramagnetic resonance spectroscopy resulting in the detection of solely monomeric [CuL]+ and [CuL2] complexes. The stability order obtained for the [CuL]+ complexes could be correlated with the deprotonation constants of their hydroxyl group (log βLH) reflecting that the higher acidity increases the complex stability in the order L2 < L1 ≈ L6 < L4 ≈ L5 < L3. This stability order elucidates the different axial linkers in the cyclic dimers 2 and 3. DFT quantum-chemical calculations support the effect of the electron distribution on the established stability order.
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Citations
Solvent induced mononuclear and dinuclear mixed ligand Cu(II) complex: structural diversity, supramolecular packing polymorphism and molecular docking studies
Mahesha,M.K. Hema,C S Karthik,K.J. Pampa,Puttaswamappa Mallu,Neratur Krishnappagowda Lokanath +5 more
TL;DR: In this article, a mixed ligand Cu(II) complex of 4,4,4-trifluoro-1-phenyl-1,3-butanedione and 8-hydroxyquinoline was synthesized and spectroscopically characterized.
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Crystal structures of zinc(II) complexes with β-hydroxypyridinecarboxylate ligands: examples of structure-directing effects used in inorganic crystal engineering
Nóra V. May,Kevin Nys,H. Y. Vincent Ching,Laura Bereczki,Tamás Holczbauer,Valerio Di Marco,Petra Bombicz +6 more
TL;DR: In this paper, the coordination properties of four hydroxy-pyri-dine-carboxylates, designed for the treatment of iron-overloading con-ditions as bidentate O,O′-donor ligands, have been studied with ZnII in the solid state.
Design of the elusive proteinaceous oxygen donor copper site suggests a promising future for copper for MRI contrast agents
TL;DR: Using a miniature artificial protein design strategy, it has been possible to prepare a newtobiology copper-binding site, one which we were surprised to find is absent in nature as mentioned in this paper .
Design of the elusive proteinaceous oxygen donor copper site suggests a promising future for copper for MRI contrast agents
Anokhi Shah,Michael J. Taylor,Sellamuthu Anbu,Margaux Verdu,Iuliia Mikulska,Sofia Diaz-Moreno,Hassane El Mkami,Graham M. Smith,Melanie M. Britton,Janet E. Lovett,Anna F. A. Peacock +10 more
TL;DR: Using a miniature artificial protein design strategy, it has been possible to prepare a new-to-biology copper-binding site, one which was surprised to find is absent in nature as mentioned in this paper .
Gradual Changes in the Aromaticity in a Series of Hydroxypyridine-Carboxylic Acid Derivatives and Their Effect on Tautomerism and Crystal Packing
Nóra V. May,G. Tamás Gál,Tamás Holczbauer,Laura Bereczki,E. Di Marco,Petra Bombicz +5 more
- 10 Jan 2024
TL;DR: This study investigates the keto-enol tautomerism and aromaticity of hydroxypyridine-carboxylic acid derivatives, revealing correlations between proton position, aromaticity, and supramolecular interactions, with implications for crystal packing and molecular properties.
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