Geometrical isomerism in octahedral complexes arising from the presence of a fused ring on a triaza macrocycle

Comba, Peter; Iuliis, Geoffry N. De; Lawrance, Geoffrey A.; Luther, Stephan; Maeder, Marcel; Nolan, Annette L.; Robertson, Mark J.; Turner, Peter

doi:10.1039/b303515h

Cited by 7 publications

(8 citation statements)

References 32 publications

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“…5HCl (5.9 g, 13 mmol) was dissolved in 100 mL water and the pH adjusted to ~6 with 2.5 M NaOH. The triamines cyclohexane-1,3,5triamine (17), 1,4,7-triaazacyclononane (18), N,N´,N´´-trimethyl-1,4,7-triaazacyclononane (19) and 2,5,8-triazabicyclo[7.4.0 1,9 ]tridecane (20) have also been reported previously [25][26][27][28], as have the dinucleating macrocycle 3,13-dimethyl-3,13-dinitro-1,5,11,15-tetraazacycloeicosane-8,18-diol (21) and its dithiol analogue (22) [29,30]. Na[CN(BH 3 )] (2.4 g, 38 mmol) was added followed by isophthalaldehyde (0.7 g, 5.2 mmol) and the pH was readjusted to 6 with 1 M HCl.…”

Section: 4-bissupporting

confidence: 64%

“…The recent observation that the monomer complex [Cu (27)] 2+ is inactive whereas the dimer analogue [Cu 2 (28)] 4+ is highly efficient as a DNA cleavage agent has highlighted the potential for dinuclear systems to act as effective artificial nucleases [67]. Systems featuring two metal centres within the one ligand may be more effective models of nucleases, where multi-metal environments are commonly met.…”

Section: Dna Cleavagementioning

confidence: 99%

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Mono- and Dinuclear Copper(II) Complexes of Pendant-Arm Macrocyclic Polyamines: Synthesis, Characterization and Investigation as Hydrolytic Cleavage Agents for DNA

McCann¹,

Iuliis²,

Lawrance³

et al. 2006

BioInorganic Reaction Mechanisms

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Section: 4-bissupporting

confidence: 64%

Section: Dna Cleavagementioning

confidence: 99%

Mono- and Dinuclear Copper(II) Complexes of Pendant-Arm Macrocyclic Polyamines: Synthesis, Characterization and Investigation as Hydrolytic Cleavage Agents for DNA

McCann¹,

Iuliis²,

Lawrance³

et al. 2006

BioInorganic Reaction Mechanisms

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“…In the major isomer, the pyridine nitrogens are trans (anti) to each other while in the minor isomer the pyridines are cis (syn) in respect of the phenolic oxygen. 39 The ORTEP 40 representation of the asymmetric unit which contains two [Zn 2 (CH 3 L4)(CH 3 COO) 2 ]PF 6 complex entities is shown (Fig. 1) complex crystallized with one Zn(II) ion six coordinate and the other in a five coordinate environment (Fig.…”

Section: Crystal Structuresmentioning

confidence: 99%

Asymmetric zinc(ii) complexes as functional and structural models for phosphoesterases

et al. 2013

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We report two asymmetric ligands for the generation of structural and functional dinuclear metal complexes as phosphoesterase mimics. Two zinc(II) complexes, [Zn 2 (CH 3 L4)(CH 3 CO 2 ) 2 ] + (CH 3 HL4 = 2-(((2-methoxyethyl)( pyridin-2-ylmethyl)amino)methyl)-4-methyl-6-((( pyridin-2-ylmethyl)amino)methyl)-phenol) and [Zn 2 (CH 3 L5)(CH 3 CO 2 ) 2 ] + (CH 3 HL5 = 2-(((2-methoxyethyl)( pyridine-2-ylmethyl)amino)-methyl)-4-methyl-6-((( pyridin-2-ylmethyl)(4-vinylbenzyl)amino)methyl)phenol) were synthesized and characterized by X-ray crystallography. The structures showed that the ligands enforce a mixed 6,5-coordinate environment in the solid state. 1 H-, 13 C-and 31 P-NMR, mass spectrometry and infrared spectroscopy were used to further characterize the compounds in the solid state and in solution. The zinc (II) complexes hydrolyzed the organophosphate substrate bis-(2,4-dinitrophenol)phosphate (BDNPP), the nucleophile proposed to be a terminal water molecule ( pK a 7.2). The ligand CH 3 HL4 was immobilised on Merrifield resin and its zinc(II) complex generated. Infrared spectroscopy, microanalysis and XPS measurements confirmed successful immobilisation, with a catalyst loading of ∼1.45 mmol g −1 resin. The resin bound complex was active towards BDNPP and displayed similar pH dependence to the complex in solution.

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“…In all cases the structures comprised the ligand monoanion, two zinc(II) ions and two bridging acetates with a hexafluorophosphate anion. The four complexes adopt the anti-configuration with respect to the plane of the phenoxide ring, 29 as does the complex [Zn 2 (CH 3 HL1)(CH 3 COO)(H 2 O)](PF 6 ).…”

Section: Solid State Structuresmentioning

confidence: 99%

The role of Zn–OR and Zn–OH nucleophiles and the influence of para-substituents in the reactions of binuclear phosphatase mimetics

et al. 2012

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Analogues of the ligand 2,2¢-(2-hydroxy-5-methyl-1,3-phenylene)bis(methylene)bis((pyridin-2-ylmethyl)azanediyl)diethanol (CH 3 H 3 L1) are described. Complexation of these analogues, 2,6-bis(((2-methoxyethyl)(pyridin-2-ylmethyl)amino)methyl)-4-methylphenol (CH 3 HL2), 4-bromo-2,6-bis(((2-methoxyethyl)(pyridin-2-ylmethyl)amino)methyl)phenol (BrHL2), 2,6-bis(((2-methoxyethyl)(pyridin-2-ylmethyl)amino)methyl)-4-nitrophenol (NO 2 HL2) and 4-methyl-2,6-bis(((2-phenoxyethyl)(pyridin-2-ylmethyl)amino)methyl)phenol (CH 3 18 O label was incorporated in the product of the hydrolysis suggesting that the nucleophile involved in the hydrolysis reaction was a Zn-OH moiety. The results are discussed with respect to the potential nucleophilic species (coordinated deprotonated alcohol versus coordinated hydroxide).

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Geometrical isomerism in octahedral complexes arising from the presence of a fused ring on a triaza macrocycle

Cited by 7 publications

References 32 publications

Mono- and Dinuclear Copper(II) Complexes of Pendant-Arm Macrocyclic Polyamines: Synthesis, Characterization and Investigation as Hydrolytic Cleavage Agents for DNA

Mono- and Dinuclear Copper(II) Complexes of Pendant-Arm Macrocyclic Polyamines: Synthesis, Characterization and Investigation as Hydrolytic Cleavage Agents for DNA

Asymmetric zinc(ii) complexes as functional and structural models for phosphoesterases

The role of Zn–OR and Zn–OH nucleophiles and the influence of para-substituents in the reactions of binuclear phosphatase mimetics

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