Copper(<scp>II</scp>)-assisted hydrolysis of 2,4,6-tris(2-pyridyl)-1,3,5-triazine. Part 1. Crystal structures of [bis(2-pyridylcarbonyl)amido](2-pyridylformamide)-copper(<scp>II</scp>) perchlorate monohydrate and [bis(2-pyridylcarbonyl)amido]-copper(<scp>II</scp>) perchlorate

Cantarero, A.; Amigó, J. M.; Faus, Juan; Julve, Miguel; Debaerdemaeker, T.

doi:10.1039/dt9880002033

Cited by 61 publications

(37 citation statements)

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“…Mono-, di-(homo-and heteronuclear), and trinuclear complexes have been reported for various divalent and trivalent metal ions (M II = Cu II , Fe II , Mn II , Co II , Ni II , and Zn II ; M III = Fe III , Rh III ). [27][28][29][30][31][32][33] Among these, a ternary complex of copper(II) with one bpca -and another derivative formed during the hydrolysis process, namely 2-picolinamide, has been described. [28] The ptO 2 -anion is obtained by means of a Cannizzaro-type reaction of pyridine-2-carboxaldehyde and NaNCO in the presence of copper metal ion.…”

Section: Introductionmentioning

confidence: 99%

“…[27][28][29][30][31][32][33] Among these, a ternary complex of copper(II) with one bpca -and another derivative formed during the hydrolysis process, namely 2-picolinamide, has been described. [28] The ptO 2 -anion is obtained by means of a Cannizzaro-type reaction of pyridine-2-carboxaldehyde and NaNCO in the presence of copper metal ion. [34] Kawijara et al have described the ptN 2 -ligand, [35] which forms when ptz is mixed with copper(II) acetate at reflux in dry MeOH in the presence of NaClO 4 .…”

Section: Introductionmentioning

confidence: 99%

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Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

et al. 2007

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The reaction of 2,4,6‐tri(pyridyl)‐1,3,5‐triazine (ptz) and copper(II) salts in dmf/water (1:1) results in the hydrolysis of ptz and formation of the anions bis(2‐pyridylcarbonyl)amide (ptO2–) and bis(2‐pyridylamine)amide (ptN2–), which are found in the complexes [Cu(ptN2)(OAc)]·3H2O (1), [Cu(ptO2)(OAc)(H2O)]·H2O (2), [Cu(ptN2)(for)]·3H2O (3) (for = formate), [Cu(ptO2)(for)(H2O)] (4), [Cu(ptO2)(benz)]·H2O (5) (benz = benzoate), and [Cu(ptO2)F(H2O)]2·3H2O (6). This report includes the chemical and spectroscopic characterization of all these complexes along with the crystal structures of 4–6. The coordination spheres of CuII in 4 and 5 are best described as distorted tetragonal square pyramidal for the former and distorted square planar for the latter. The crystal structure of 6 shows the presence of two discrete monomeric [Cu(ptO2)F(H2O)] entities in the crystallographic asymmetric unit in which both copper(II) ions have a distorted square‐pyramidal coordination geometry. The binding of the complexes to DNA has been investigated with the aid of viscosity and thermal denaturation studies, both of which indicate that the interaction is probably due to the outer‐sphere mechanism. The ability of the compounds to cleave DNA has also been tested. Efficient oxidative cleavage was observed in the presence of a mild reducing agent (ascorbate) and dioxygen. Mechanistic studies with reactive oxygen species (ROS) scavengers confirm that hydrogen peroxide, the hydroxyl radical, singlet oxygen‐like species, and the superoxide anion are necessary diffusible intermediates in the scission process. A mechanism involving either the Fenton or theHaber–Weiss reaction plus the formation of copper oxene species is proposed for the DNA cleavage mediated by these compounds.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

et al. 2007

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“…Several reports have described that coordination of one metal ion, especially Cu II , to tptz induces the hydrolysis of tptz to form bis(2-pyridylcarbonyl)amine and its complexes. [22,23] In order to use tptz as a ferromagnetic coupler between three transition metal ions we investigated whether complexes with tptz as a bridging ligand between three metal ions in bipyridine-like sites would be accessible (V in Scheme 1). Herein we report the reaction of tptz with an excess of Cu II ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structures, and Magnetic Properties of a Mono‐ and a Dinuclear Copper(II) Complex of the 2,4,6‐Tris(2‐pyridyl)‐1,3,5‐triazine Ligand

2004

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The reaction of 2,4,6‐tris(2‐pyridyl)‐1,3,5‐triazine (tptz) with Cu(BF4)2·3H2O and N,N‐bis(3‐aminopropyl)methylamine (Medpt) yielded the monomeric complex [(tptz)CuII(Medpt)](BF4)2·2MeOH (1) whereas reaction of tptz with CuCl2·2H2O yielded the dinuclear complex [{CuIICl2}(tptz){CuIICl2(MeOH)}] (2). The molecular structures of 1 and 2 were established by single‐crystal X‐ray diffraction studies. The copper ion in complex 1 is elongated octahedral with the nitrogen atoms of Medpt and the triazine nitrogen atom of tptz in the equatorial positions, and the two pyridyl nitrogen atoms of tptz in axial positions. The two CuII ions in complex 2 are bridged by tptz, coordinating to Cu1 in a terpyridine‐like fashion and to Cu2 in a bipyridine‐like coordination mode. The triazine nitrogen atom bound to Cu1 is coordinated in an equatorial position whereas the triazine nitrogen atom bound to Cu2 is situated in the apical position. The equatorial plane of Cu1 is coplanar with the 1,3,5‐triazine plane whereas the equatorial plane of Cu2 is perpendicular to the 1,3,5‐triazine plane. Intermolecular interactions in the solid state result in both compounds in “dimeric units” due to hydrogen bonding. Both complexes were investigated by variable‐temperature magnetic susceptibility measurements. Through‐space dipolar couplings and/or weak through‐bond interactions in complex 1 result in a small intermolecular antiferromagnetic interaction (J = −0.09 cm−1). The intramolecular exchange coupling in the dinuclear complex 2 is antiferromagnetic (J = −2.5 cm−1). This antiferromagnetic interaction was analyzed in view of the molecular structure considering spin‐polarization, superexchange and orbital‐orthogonality. A spin‐polarization pathway seems to be the leading contribution which does not involve the 1,3 bridging pathway. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…However, in the presence of copper(II) ions, hydrolysis occurs under mild conditions to afford the highly stable bis(2-arylcarbonyl) amidocopper(II) species [Cu(bpcam)] + (tpymt) and [Cu(bpca)] + (tpyt) [4,5]. While other first-row transition metal ions are unable to cause this hydrolysis, it has recently been shown that Rh(III) promotes the hydrolysis of tptz yielding the same fragments [6].…”

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confidence: 99%

Design of single cyanide-bridged tetranuclear bimetallic rectangles exhibiting ferromagnetic coupling

Toma¹,

Lescouëzec²,

Cangussu³

et al. 2005

Inorganic Chemistry Communications

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Copper(II)-assisted hydrolysis of 2,4,6-tris(2-pyridyl)-1,3,5-triazine. Part 1. Crystal structures of [bis(2-pyridylcarbonyl)amido](2-pyridylformamide)-copper(II) perchlorate monohydrate and [bis(2-pyridylcarbonyl)amido]-copper(II) perchlorate

Abstract: Copper( 11)-assisted Hydrolysis of 2,4,6-Tris(2-pyridyl)-I ,3,5-triazine. Part 1. Crystal Structures of [ bis(2-pyridylcarbonyl)amido] (2-pyridy1formamide)copper( 11) Perchlorate Monohydrate and [ Bis(2-pyridylcarbonyl)amido]copper( 11) Perchlorate t

Cited by 61 publications

References 6 publications

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

Synthesis, Crystal Structures, and Magnetic Properties of a Mono‐ and a Dinuclear Copper(II) Complex of the 2,4,6‐Tris(2‐pyridyl)‐1,3,5‐triazine Ligand

Design of single cyanide-bridged tetranuclear bimetallic rectangles exhibiting ferromagnetic coupling

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