Dimeric copper(<scp>II</scp>) compounds with a tripodal imidazole-containing ligand and bridged by imidazolate, benzimidazolate, and benzotriazolate ions. Crystal and molecular structure of µ-(benzotriazolato-N1,N3)bis{[tris(N1-methylbenzimidazol-2-ylmethyl)amine-N,N3,N3′,N3″]copper(<scp>II</scp>)} trinitrate

Hendriks, H. M. J.; Birker, P. J. M. W. L.; Verschoor, G. C.; Reedijk, Jan

doi:10.1039/dt9820000623

Cited by 90 publications

(30 citation statements)

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“…[43]- [46] The shift d pc was calculated for the protons of the six histidines in the activate site of Limulus polyphemus hemocyanin (PDB 1OXY) and catechol oxidase from Ipomoea batatas (PDB 1BT3) by placing a magnetic dipole (S = 1 = 2 ) on each of the two Cu centres and averaging their contributions (see Table S1 in the Supporting Information). For only two out of the 18 protons, j d pc j amounts to about 4 ppm, while for almost all other cases j d pc j is < 2 ppm.…”

Section: Methodsmentioning

confidence: 99%

Paramagnetic Properties of the Halide‐Bound Derivatives of Oxidised Tyrosinase Investigated by ¹H NMR Spectroscopy

Tepper

Bubacco

Canters

2006

Chemistry A European J

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The (1)H NMR relaxation characteristics of the histidines in the oxidised type-3 copper site of tyrosinase (Ty(met)) from the bacterium Streptomyces antibioticus in the halide-bound forms (Ty(met)X with X = F(-), Cl(-), Br(-)) have been determined and analysed. The (1)H NMR spectra of the Ty(met)X species display remarkably sharp, well-resolved, paramagnetically shifted (1)H signals, which originate from the protons of the six His residues coordinated to the two Cu(II) ions in the type-3 centre. From the temperature-dependence of the (1)H paramagnetic shifts the following values for the exchange-coupling parameter -2J were determined: 260 (Ty(met)F), 200 (Ty(met)Cl) and 162 cm(-1) (Ty(met)Br). The (1)H T(1) relaxation is dipolar in origin and correlates with the Cu--H distances. Electronic relaxation times tau(S) derived from the (1)H T(1) data amount to about 10(-11) s and follow the order Ty(met)F>Ty(met)Cl>Ty(met)Br. They are two orders of magnitude shorter than the tau(S) values reported for mononuclear copper systems, in accordance with the sharpness of the (1)H signals. The results corroborate the Cu(2) bridging mode of the halide ions. On the basis of the measured hyperfine interaction constants for the ligand histidine nuclei, it is concluded that 70-80 % of the spin density in the excited triplet state resides on the two copper ions and the bridging atoms.

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Section: Methodsmentioning

confidence: 99%

Paramagnetic Properties of the Halide‐Bound Derivatives of Oxidised Tyrosinase Investigated by ¹H NMR Spectroscopy

Tepper

Bubacco

Canters

2006

Chemistry A European J

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“…The bond distances between the zinc atom and the apical nitrogen atom, i.e., Zn(1)-N(11), Zn(2)-N(1), are 2.395(8) and 2.409(9) Å , respectively, which are about 0.35 Å longer than the bond distances between the zinc atom and the trigonal basal nitrogen atoms (Zn(1): 2.057-2.066 Å , average 2.062 Å ; Zn(2): 2.022-2.065 Å , average 2.04 Å ). This significant elongation has been observed previously in zinc complexes of tripodal tetradentate ligands with benzimidazolylmethyl groups [27,34].…”

Section: X-ray Structures Of the Complexesmentioning

confidence: 55%

“…Yield: 4.6 g (51%); m. p.: 215-217°C (literature value 215°C [27]). The 1 H NMR spectrum of the ligand was consistent with the literature [28].…”

Section: Preparation Of Mentbmentioning

confidence: 99%

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Synthesis, structure, and DNA-binding properties of manganese(II) and zinc(II) complexes with tris(N-methylbenzimidazol-2-ylmethyl)amine ligand

Sun

et al. 2010

Transition Met Chem

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Tris(N-methylbenzimidazol-2-ylmethyl)amine (Mentb) and its two complexes, [Mn(Mentb)(DMF)-(H 2 O)](pic) 2 1 and [Zn(Mentb)(pic)](pic) 2 (pic = picrate), have been synthesized and characterized by physico-chemical and spectroscopic methods. Single crystal X-ray diffraction revealed that the two complexes have different structures. In complex 1, the coordination sphere around Mn(II) is distorted octahedral, whereas in complex 2 the coordination sphere around Zn(II) is distorted trigonal bipyramidal. The DNA-binding properties of the free ligand and its two complexes have been investigated by electronic absorption, fluorescence, and viscosity measurements. The results suggest that the ligand and its two complexes bind to DNA via an intercalation binding mode, and their binding affinity for DNA follows the order 1 [ 2 [ ligand.

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“…For example, superoxide dismutases (SOD), which are contained in microbes, plants and animals, protects cells against oxygen toxicity, because these enzymes catalyse the conversion of superoxide to hydrogen peroxide and dioxygen via redoxactive metals [2,3]. The tetradentate tripodal ligand, tris(1-methylbenzimidazol-2-ylmethyl)amine, is similar to the histidine imidazole in coordination aspects [4,5]. Since the three arms of this type of ligand can each rotate freely around an N(apical)-Cbond, multicomponent complexes or coordination polymeric networks may be expected to form the assembly of this ligand by metal ions of low coordination number.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of [cinnamato-[tris(1-methylbenzimidazol-2-ylmethyl)- amine]-zinc(II)] perchlorate —dimethylformamide — methanol (1:1:2:0.5), [Zn(C27H27N7)(C9H7O2)](ClO4) · 2(CH3)2NCHO · 0.5CH3OH

Wu¹,

Yun²,

Yuan³

et al. 2008

Zeitschrift Für Kristallographie - New Crystal Structures

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C 42.50H50ClN9O8.50Zn, monoclinic, C12/c1(no. 15 Source of materialReagents and solvents used were of commercially available quality. To as tirred solution of tris(1-methylbenzimidazol-2-ylmethyl)amine (89.9 mg, 0.2 mmol) in hot MeOH (10 ml) Zn(ClO 4 ) 2 (H 2 O) 6 (74.5 mg, 0.2 mmol) was added ,followed by a solution of sodium cinnamate (34.0 mg, 0.2 mmol) in MeOH (5 ml). Acolorless crystalline product formed rapidly. Experimental DetailsAll Ha toms were found in difference electron maps and were subsequently refined in ar iding-model approximation with C-H distances ranging from 0.95 to 0.99 Å and O-H distance 0.84 Å and U iso(H) =1.2 Ueq of the carrier atom. DiscussionModel systems that mimic the active sites of metalloenzymes are important not only for the understanding of enzyme mechanisms, but also for the development biomimetic catalysts with low molecular weight. Histidine imidazole plays an important role in the coordination of manganese at the active sites of numerous proteins [1]. For example, superoxide dismutases (SOD), which are contained in microbes, plants and animals, protects cells against oxygen toxicity, because these enzymes catalyse the conversion of superoxide to hydrogen peroxide and dioxygen via redoxactive metals [2,3]. The tetradentate tripodal ligand, tris(1-methylbenzimidazol-2-ylmethyl)amine, is similar to the histidine imidazole in coordination aspects [4,5]. Since the three arms of this type of ligand can each rotate freely around an N(apical)-Cbond, multicomponent complexes or coordination polymeric networks may be expected to form the assembly of this ligand by metal ions of low coordination number. In the crystal structure of the title mononuclear zinc(II) complex, the asymemetric unit consists of a[ Zn(tris(1-methylbenz imidazol-2-ylmethyl)amine) (cinnamato)] + cation, aperchlorate anion, two DMF molecules and half methanol molecule. The tripodal ligand tris(1-methylbenzimidazol-2-ylmethyl)amine forms atripodal pyramidal environment around zinc, and the remaining open axial site of the complex is occupied by a cinnamato anion. The zinc(II) atom is five-coordinated with a N 4Oligand donor set and has adistorted trigonal bipyramidal environments. All the bond lengths related to the zinc atom are comparable to the values observed in other complexes [6,7]. The atoms of the cinnamate ligand are disordered over two sites of approximately 2.1 :1occupancy. The lattice methanol molecule is disordered over two positions with equal occupancy. Two DMF molecules are also disordered.

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Dimeric copper(II) compounds with a tripodal imidazole-containing ligand and bridged by imidazolate, benzimidazolate, and benzotriazolate ions. Crystal and molecular structure of µ-(benzotriazolato-N¹,N³)bis{[tris(N¹-methylbenzimidazol-2-ylmethyl)amine-N,N³,N³′,N³″]copper(II)} trinitrate

Cited by 90 publications

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Paramagnetic Properties of the Halide‐Bound Derivatives of Oxidised Tyrosinase Investigated by ¹H NMR Spectroscopy

Paramagnetic Properties of the Halide‐Bound Derivatives of Oxidised Tyrosinase Investigated by ¹H NMR Spectroscopy

Synthesis, structure, and DNA-binding properties of manganese(II) and zinc(II) complexes with tris(N-methylbenzimidazol-2-ylmethyl)amine ligand

Crystal structure of [cinnamato-[tris(1-methylbenzimidazol-2-ylmethyl)- amine]-zinc(II)] perchlorate —dimethylformamide — methanol (1:1:2:0.5), [Zn(C27H27N7)(C9H7O2)](ClO4) · 2(CH3)2NCHO · 0.5CH3OH

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Dimeric copper(II) compounds with a tripodal imidazole-containing ligand and bridged by imidazolate, benzimidazolate, and benzotriazolate ions. Crystal and molecular structure of µ-(benzotriazolato-N1,N3)bis{[tris(N1-methylbenzimidazol-2-ylmethyl)amine-N,N3,N3′,N3″]copper(II)} trinitrate

Cited by 90 publications

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Paramagnetic Properties of the Halide‐Bound Derivatives of Oxidised Tyrosinase Investigated by 1H NMR Spectroscopy

Paramagnetic Properties of the Halide‐Bound Derivatives of Oxidised Tyrosinase Investigated by 1H NMR Spectroscopy

Synthesis, structure, and DNA-binding properties of manganese(II) and zinc(II) complexes with tris(N-methylbenzimidazol-2-ylmethyl)amine ligand

Crystal structure of [cinnamato-[tris(1-methylbenzimidazol-2-ylmethyl)- amine]-zinc(II)] perchlorate —dimethylformamide — methanol (1:1:2:0.5), [Zn(C27H27N7)(C9H7O2)](ClO4) · 2(CH3)2NCHO · 0.5CH3OH

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Dimeric copper(II) compounds with a tripodal imidazole-containing ligand and bridged by imidazolate, benzimidazolate, and benzotriazolate ions. Crystal and molecular structure of µ-(benzotriazolato-N¹,N³)bis{[tris(N¹-methylbenzimidazol-2-ylmethyl)amine-N,N³,N³′,N³″]copper(II)} trinitrate

Paramagnetic Properties of the Halide‐Bound Derivatives of Oxidised Tyrosinase Investigated by ¹H NMR Spectroscopy

Paramagnetic Properties of the Halide‐Bound Derivatives of Oxidised Tyrosinase Investigated by ¹H NMR Spectroscopy