Synthesis and electronic properties of transition metal complexes containing sulfonamidoquinoline ligands

Gole, Matthew T.; Pauls, Patrick; Hartlaub, Sage F.; Nataro, Chip; Rossiter, Lauren M.; O’Connor, Abby R.; Chan, Benny C.

doi:10.1016/j.poly.2021.115269

Cited by 2 publications

(3 citation statements)

References 32 publications

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“…The Zn-ligand bonding take place trough Zn-Nquinoline and Zn-Nsulfonamide bonds. The Zn-Nquinoline bond lengths (0.20426 and 0.20299 nm) are slightly larger than Zn-Nsulfonamide bonds (0.19729 and 0.19883 nm) but in an acceptable range as reported by other authors for similar complexes [9,20]. The bond lengths between nitrogen and sulfur atoms from sulfonamide moiety (N2-S1 = 0.15993 nm, N4-S2 = 0.15883 nm) and between nitrogen atoms from sulfonamide and corresponding quinoline carbon (N2-C8 = 0.1398 nm, N4-C23 = 0.1406 nm) are typical for these sort of bonds.…”

Section: Results and Its Discussionsupporting

confidence: 68%

“…The merge of the two moieties, quinoline and sulfonamide, followed by complexation with different metals, are leading to an interesting new class of compounds, namely quinoline sulfonamide complexes QSCM. The QSCM derivatives pay a particularly attention on scientific community during the last few years, especially for their fotoluminiscent [9][10][11][12] and biological properties. As far for biological properties, these compounds were found to have several activities, these including antiprotozoals and antimalarial and also antibacterial and antifungal activity [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

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MATERIALS BASED ON QUINOLINE SULFONAMIDE - METALS WITH ANTIMICROBIAL ACTIVITY AND THEIR X-Ray characterisation

Diaconu

Mangalagiu

CIORTEANU

et al. 2022

METAL 2022 Conference Proeedings

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Quinoline sulfonamide complexes with different metals represent a new class of materials of great interest especially for their fotoluminiscent and biological activity (mostly antibacterial and antifungal activity). The emphasis of this work was to synthesize, characterize through X-ray and determine the antibacterial and antifungal proprieties of newly materials for medicinal chemistry applications based on Quinoline Sulfonamide Complexes Metals (QSCM). The synthesis of the QSCM materials is straight and efficient, in two steps: acylation of aminoquinoline followed by complexation with M 2+ metal (Zn 2+ , Cd 2+ , Co 2+ , Cu 2+ ). The synthesized quinoline sulfonamide complexes M 2+ metals were characterized by X-ray diffraction on single crystal and by FTIR and NMR spectroscopy. The X-ray spectra prove unambiguously the structure of complexes, e.g for the Zn (II) complex crystallize in the monoclinic P21/n space group type, with a = 1.21602(5) nm, b = 1.55478(5) nm, c = 1.61786(6) nm, α = 90°, β = 106.007(2)°, γ = 90°, V = 2.9402(19) nm 3 and Z = 4. Sulfonamide acts as bidentate ligand trough Zn-Nquinoline and Zn-Nsulfonamide bonds, with a tetrahedral coordination environment for Zn 2+ . The QSCM M 2+ complexes were tested for their antibacterial and antifungal activity, having a good antibacterial activity against gram positive germ Staphylococcus aureus, and gram negative germ Escherichia coli, and an excellent antifungal activity against fungus Candida albicans.

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Section: Results and Its Discussionsupporting

confidence: 68%

Section: Introductionmentioning

confidence: 99%

MATERIALS BASED ON QUINOLINE SULFONAMIDE - METALS WITH ANTIMICROBIAL ACTIVITY AND THEIR X-Ray characterisation

Diaconu

Mangalagiu

CIORTEANU

et al. 2022

METAL 2022 Conference Proeedings

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“…In addition, periphery sulfonyl groups may aid in second coordination sphere H-bonding and water solubility. Ligands that employ secondary sulfonamido donors typically contain a tosyl-, − dansyl-, or quinoyl sulfonamido , donor in a terminal position. There are only a few examples with sulfonamide groups in non-terminal positions.…”

Section: Introductionmentioning

confidence: 99%

Sulfonamido-Pincer Complexes of Cu(II) and the Electrocatalysis of O₂ Reduction

et al. 2023

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Heteroleptic copper complexes of an asymmetrical pincer ligand containing a central anionic sulfonamide donor (pyridine-2-yl-sulfonyl)(quinolin-8yl)-amide (psq), which contains a central anionic sulfonamido donor have been prepared. Meridional κ 3 -N,N″,N‴ binding with the co-ligands acetate, chloride, or acetonitrile (MeCN), trans to the central sulfonamido N-donor, is revealed by the Xray crystal structures of [Cu(OAc)(psq)(H 2 O)], [CuCl(psq)] 2 , and [Cu(psq)-(MeCN)](PF 6 ). Either overall distorted square pyramidal or octahedral geometries of the copper atom are satisfied by coordinated water in the case of the acetate complex or interactions with periphery sulfonamido oxygen atoms on adjacent molecules in the dimeric chloride and 1D polymeric acetonitrile complexes. The cyclic voltammogram (CV) of [Cu(OAc)(psq)(H 2 O)] shows a quasi-reversible Cu II /Cu I reduction at −0.930 V (vs Fc + /Fc 0 , MeCN), and an irreversible Cu II /Cu I reduction for [Cu(psq)(MeCN)](PF 6) is seen at −0.838 V. This signal is split into two quasi-reversible redox processes on the addition of 2,2,2-trifluoroethanol (TFE). This suggests that TFE pushes a solution equilibrium toward a dimeric acetate complex analogous to [CuCl(psq)] 2 , which shows two quasi-reversible waves at −0.666 V and −0.904 V vs Fc + /Fc 0 consistent with its dimeric solid-state structure. A comparison of the CVs of [Cu(OAc)(psq)(H 2 O)] under either a N 2 or an O 2 atmosphere revealed that this complex catalyzes turnover electro-reduction of O 2 to H 2 O 2 and H 2 O. The rate of reaction increases on addition of a weak organic acid, and a coulombic efficiency of 48% for H 2 O 2 was determined by iodometric titration. We propose that a Cu I complex formed on electroreduction binds O 2 to yield an intermediate superoxide complex. On electron and proton transfer to this species, a bifurcated route back to the O 2 -activating Cu I complex is feasible with either release of H 2 O 2 or O−O cleavage resulting in the liberation of H 2 O. The Cu I complex is regenerated by subsequent reduction and protonation to close the cycle.

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Synthesis and electronic properties of transition metal complexes containing sulfonamidoquinoline ligands

Cited by 2 publications

References 32 publications

MATERIALS BASED ON QUINOLINE SULFONAMIDE - METALS WITH ANTIMICROBIAL ACTIVITY AND THEIR X-Ray characterisation

MATERIALS BASED ON QUINOLINE SULFONAMIDE - METALS WITH ANTIMICROBIAL ACTIVITY AND THEIR X-Ray characterisation

Sulfonamido-Pincer Complexes of Cu(II) and the Electrocatalysis of O₂ Reduction

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Synthesis and electronic properties of transition metal complexes containing sulfonamidoquinoline ligands

Cited by 2 publications

References 32 publications

MATERIALS BASED ON QUINOLINE SULFONAMIDE - METALS WITH ANTIMICROBIAL ACTIVITY AND THEIR X-Ray characterisation

MATERIALS BASED ON QUINOLINE SULFONAMIDE - METALS WITH ANTIMICROBIAL ACTIVITY AND THEIR X-Ray characterisation

Sulfonamido-Pincer Complexes of Cu(II) and the Electrocatalysis of O2 Reduction

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Sulfonamido-Pincer Complexes of Cu(II) and the Electrocatalysis of O₂ Reduction