Dinuclear ruthenium complexes containing a new ditopic phthalazin-bis(triazole) ligand that promotes metal–metal interactions

Aguiló, Joan; Naeimi, Atena; Bofill, Roger; Müeller-Bunz, Helge; Llobet, Antoni; Escriche, Lluís; Sala, Xavier; Albrecht, Martin

doi:10.1039/c3nj01209c

Cited by 18 publications

(18 citation statements)

References 78 publications

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“…All resonances could be unambiguously assigned based on their integrals, multiplicity and the C 2v symmetry of the ligand in solution. For L1 2+ , both H9 and H10 (or H9' and H10') display a doublet of doublets with a mirror effect, which is in agreement with the typical AA'BB' (9 9'10 10' in our case) pattern of this kind of systems, 10 as shown in the inset of Fig. 1.…”

Section: Transfac-[ru(phthapz-ome)(bpea)x]supporting

confidence: 74%

Mononuclear ruthenium compounds bearing N-donor and N-heterocyclic carbene ligands: structure and oxidative catalysis

et al. 2017

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A new CNNC carbene-phthalazine tetradentate ligand has been synthesized, which under reaction with [Ru(T)Cl3] (T = trpy, tpm, bpea; trpy = 2,2';6',2"-terpyridine; tpm = tris(pyrazol-1-yl)methane; bpea = N,N-bis(pyridin-2-ylmethyl)ethanamine) in MeOH or iPrOH undergoes a C-N bond scission due to the nucleophilic attack of a solvent molecule, with the subsequent formation of the mononuclear complexes cis- [Ru(PhthaPz-OR) , where Ru(III) is almost unstable with regards to its disproportion. The catalytic performance of the Ru-OH2 complexes in chemical water oxidation at pH 1.0 points to poor stability (ligand oxidation), with subsequent evolution of CO2 together with O2, specially for 4 2+ and 6 2+ . In electrochemically driven water oxidation, higher TOF values are obtained for 2a 2+ at pH 1.0. In alkene epoxidation, complexes favouring bi-electronic transfer processes show better performance and selectivity than those favouring monoelectronic transfers, while alkenes containing electron-donor groups promote better performance than those bearing electron-withdrawers. Finally, when cis-β-methylstyrene is employed as substrate, no cis/trans isomerization takes place, thus indicating the existence of an stereospecific process.

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Section: Transfac-[ru(phthapz-ome)(bpea)x]supporting

confidence: 74%

Mononuclear ruthenium compounds bearing N-donor and N-heterocyclic carbene ligands: structure and oxidative catalysis

et al. 2017

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“…Click chelators with a variety of N-donor units connected at the 4-triazolyl position have been reported, including pyridine [12–17], quinoline [18–19], pyridazine [20–21], phthalazine [22], benzimidazole [23], phenanthroline [24], bipyridine [25] and amine [26] subunits. The utility of such chelators in constructing coordination compounds has been demonstrated for a wide range of transition metal and lanthanide cations, and have impacted fields that include bioimaging [26–27] and chemosensing [28–29].…”

Section: Introductionmentioning

confidence: 99%

Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles

Fletcher¹,

Hanson²,

Christensen³

et al. 2018

Beilstein J. Org. Chem.

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The 1-substituted-4-imino-1,2,3-triazole motif is an established component of coordination compounds and bioactive molecules, but depending on the substituent identity, it can be inherently unstable due to Dimroth rearrangements. This study examined parameters governing the ring-degenerate rearrangement reactions of 1-substituted-4-imino-1,2,3-triazoles, expanding on trends first observed by L’abbé et al. The efficiency of condensation between 4-formyltriazole and amine reactants as well as the propensity of imine products towards rearrangement was each strongly influenced by the substituent identity. It was observed that unsymmetrical condensation reactions conducted at 70 °C produced up to four imine products via a dynamic equilibrium of condensation, rearrangement and hydrolysis steps. Kinetic studies utilizing 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbaldehyde with varying amines showed rearrangement rates sensitive to both steric and electronic factors. Such measurements were facilitated by a high throughput colorimetric assay to directly monitor the generation of a 4-nitroaniline byproduct.

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“…[1][2][3] However, the intensive use of triadimefon and its single acting mechanism and active site have led to substantial environmental contamination and a rapid selection of resistance strains in both China and many other countries. [6][7][8][9] The pharmacological and toxicological properties of many drugs are modified when they form metallic complexes. This is due to their novel structures and potential applications especially in the pharmaceutical industry and agriculture.…”

Section: Introductionmentioning

confidence: 99%

Two Cu(ii) complexes of triadimefon: crystal structure, antifungal activities and structure–activity relationship

Yan

et al. 2015

New J. Chem.

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Two Cu(II) complexes, [CuL 2 Cl 2 (EtOH)] 1 and [CuL 4 (NO 3 ) 2 ]Á0.5H 2 O 2 (L = 1-(4-chlorophenoxy)-3,3dimethyl-1-H(1,2,4-triazole-1-y)-2-butanone, triadimefon) have been synthesized and their structures were determined by single crystal X-ray diffraction (XRD). Crystal structural analysis shows that in complex 1, the copper cation lies on a crystallographic inversion center and is coordinated with two triazole groups, two chloride ligands and an ethanol molecule. In each unit cell, two pairs of adjacent [CuL 2 Cl 2 (EtOH)] molecules are linked by O-HÁ Á ÁCl hydrogen bonds to form a 2D plane. Complex 2 is octahedral with the metal cation bound to four triazole groups and two nitrate ligands. The geometry is elongated due to the more distant interactions between connecting nitrate O atoms and the Cu cation.The two complexes were screened for antifungal activities against five selected fungi using the mycelial growth rate method. The synergistic interactions between Cu 2+ and triadimefon were also investigated by the Wadley approach, and the results reveal that the synergy levels for the ratio 1 : 4 of the molecular-level mixture of Cu 2+ and triadimefon are better than that for the ratio 1 : 2. To better understand the structure-activity relationship, theoretical investigation of the electronic structure of the metal complexes has been carried out using density function theoretical (DFT) calculations. The results indicated that the Cu cation and the triazole originating from triadimefon are the active sites, and the decrease of the polarity of Cu 2+ can contribute to the increased biocidal properties after complexation since it is responsible for the enhanced penetration of the metal complexes into the lipid membranes.

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Dinuclear ruthenium complexes containing a new ditopic phthalazin-bis(triazole) ligand that promotes metal–metal interactions

Cited by 18 publications

References 78 publications

Mononuclear ruthenium compounds bearing N-donor and N-heterocyclic carbene ligands: structure and oxidative catalysis

Mononuclear ruthenium compounds bearing N-donor and N-heterocyclic carbene ligands: structure and oxidative catalysis

Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles

Two Cu(ii) complexes of triadimefon: crystal structure, antifungal activities and structure–activity relationship

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