Chelating ability of a conjugated redox active tetrathiafulvalenyl-acetylacetonate ligand

Bellec, Nathalie; Massue, Julien; Roisnel, Thierry; Lorcy, Dominique

doi:10.1016/j.inoche.2007.07.003

Cited by 31 publications

(18 citation statements)

References 32 publications

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“…Acetylacetone (acac) or pentane-2,4-dione is often used as a good precursor in organic synthesis and as a building block of metal-organic complexes [1,2]. Its anion acts as the bidentate ligand and is known to form complexes with many transition metal ions [3][4][5].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Antibacterial Studies and Crystal Structures of Tridentate Schiff Base Ligand and It’s Cobalt(III) Complex

et al. 2012

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The crystal structures of 4-[(2-hydroxyphenyl) imino]-2-pentanone (H 2 hpac, 1) and its cobalt(III) complex [Co III (hpac)py 3 ] ? ÁPF 6 -(2) have been determined by X-ray diffraction. The ligand 1 crystallizes in orthorhombic chiral P2 1 2 1 2 1 space group, with a = 8.8405(4) Å , b = 10.5349(8) Å , c = 11.2292)7( Å ), and the complex 2-in the centrosymmetric monoclinic P2/n space group, with a = 16.496(5) Å , b = 10.171(2) Å , c = 16.646(5) Å , and b = 95.53(3)°. In the ligand molecule quite strong intramolecular hydrogen bond closes six-membered ring. The bond length pattern within this ring suggests the significant conjugation and the structure might be therefore regarded as the intermediate between keto-enamine and zwitterionic forms, and the intramolecular hydrogen bond falls into category of resonance-assisted hydrogen bonds. In turn, intermolecular O-HÁÁÁO hydrogen bonds connect the molecules of the ligand into infinite chains along [100] direction. In the complex, the Co(III) ion is hexa-coordinated, by two oxygen and one nitrogen atoms of the doubly-deprotonated ligand 1 and by three nitrogen atoms from three pyridine ligands. The coordination polyhedron is close to a slightly distorted octahedron. The in vitro antimicrobial activity of the Schiff base ligand and its corresponding complex have been tested against human pathogenic bacterias such as Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli.Keywords Schiff base Á Tridentate ligands Á Co complex Á Hydrogen bonds Á Biological activity Results and DiscussionAcetylacetone (acac) or pentane-2,4-dione is often used as a good precursor in organic synthesis and as a building block of metal-organic complexes [1,2]. Its anion acts as the bidentate ligand and is known to form complexes with many transition metal ions [3][4][5]. A general method of preparation of such complexes consists in a reaction of a metal ion with acetylacetone in presence of a base which easily separates the proton. Replacement of the ketone functional group by the imine one results in corresponding bidentate Schiff bases, which also proved to be useful ligands. If 2-hydroxy aniline is used as the amine, one can prepare the tridentate ligand. Such a ligand-4-[(2-hydroxyphenyl)imino]-2-pentanone (hereafter referred to as 1), known as H 2 hpac, where H 2 represents the dissociable enolic -OH and hydroxyphenyl protons-has been already prepared and used for making the square-planar mixed-ligand nickel(II) complex with deprotonated H 2 hpac (i.e. hpac), which coordinates through the enolate oxygen, the imine nitrogen and the deprotonated hydroxyphenyl oxygen atoms. Additionally, the neutral N-donor, imidazole, has been used as an ancillary ligand [6]. Such

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Section: Resultsmentioning

confidence: 99%

Synthesis, Antibacterial Studies and Crystal Structures of Tridentate Schiff Base Ligand and It’s Cobalt(III) Complex

et al. 2012

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“…17.25 ppm) arising from acetylacetonate indicates the keto–enol tautomerism of the ligands. Complexes 1 – 8 show sharp absorption bands at around 1567 and 1477 cm –1 in their IR spectra, which are indicative of β‐diketonate moieties chelating to the metal ions 14a,14b,19. Thermogravimetric analysis (TGA) of 1 showed the first weight loss at 139 °C, which corresponds approximately to the loss of solvent molecules.…”

Section: Resultsmentioning

confidence: 99%

Mono‐ and Dinuclear Co/Ni Complexes Bearing Redox‐Active Tetrathiafulvaleneacetylacetonate Ligands – Syntheses, Crystal Structures, and Properties

Xiong

Sun

et al. 2011

Eur J Inorg Chem

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“…The coordination chemistry of two of these ligands towards the metallic center also generates various dimeric structures [10][11][12]. Most of the interactions detected through organic linkers are weak and coordination chemistry does not allow an increase of electronic interplay [13][14][15]. On the other hand, the use of an organometallic linker such as the trans bis(acetylide) ruthenium one in trans-[Ru(C≡CMe 3 TTF) 2 (dppe) 2 ] mediates strong electronic coupling between the two TTFs [16].…”

Section: Introductionmentioning

confidence: 99%

Metal (Hg, Pt, Ru) Bisalkynyl Bridge between Tetrathiafulvalene Electrophores and Electronic Interplay

et al. 2018

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A series of metal (Hg, Pt, Ru) bis(alkynyl-tetrathiafulvalene) complexes have been investigated to study the electronic interplay between the metal and the tetrathiafulvalene (TTF), as well as between the two peripheral TTF electrophores along the organometallic bridge. Cyclic voltammetry experiments, together with spectro-electrochemical investigations, have shown the electronic effect of the metal center through the linker on redox properties of the TTF, as well as the influence of the length of the conjugated organic linker. These data show that the degree of coupling can be modulated from no coupling with mercury to appreciable electronic coupling between different electrophores with ruthenium.

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Chelating ability of a conjugated redox active tetrathiafulvalenyl-acetylacetonate ligand

Cited by 31 publications

References 32 publications

Synthesis, Antibacterial Studies and Crystal Structures of Tridentate Schiff Base Ligand and It’s Cobalt(III) Complex

Synthesis, Antibacterial Studies and Crystal Structures of Tridentate Schiff Base Ligand and It’s Cobalt(III) Complex

Mono‐ and Dinuclear Co/Ni Complexes Bearing Redox‐Active Tetrathiafulvaleneacetylacetonate Ligands – Syntheses, Crystal Structures, and Properties

Metal (Hg, Pt, Ru) Bisalkynyl Bridge between Tetrathiafulvalene Electrophores and Electronic Interplay

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