Crystal structures and magnetic properties of bi- and tetra-nuclear copper(<scp>II</scp>) complexes of 2,6-diformyl-4-methylphenol di(benzoylhydrazone)

Sakamoto, Masatomi; Itose, Shoichi; Ishimori, Tomitaro; Matsumoto, Naohide; Ökawa, Hisashi; Kida, Sigeo

doi:10.1039/dt9890002083

Cited by 37 publications

(12 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The formation of similar di‐ and tetranuclear structures based on bis‐hydrazones or bis‐thiosemicarbazones has been reported before: In rare cases, “in situ” aromatic ligand hydroxylation was also observed 22,23. As in compound 1 , dinuclear complexes can be stabilized by an exogenous monodentate and monoanionic ligand (hydroxide,22,24 ethanolate,25 chloride,23 methanolate,22,26,27 or azide28).…”

Section: Resultssupporting

confidence: 69%

Reaction of a Bis(benzoylhydrazone) with Copper(II): Complex Formation, Hydroxylation, and DNA Cleavage Activity

et al. 2013

View full text Add to dashboard Cite

The reaction of the ditopic bis(benzoylhydrazone) of isophthalaldehyde (H2L) with copper(II) acetate in methanol under aerobic conditions afforded a green solid that contains the tetranuclear complex [Cu4L*2(OCH3)2] (1). The ligand L*, a bis(benzoylhydrazone) of 2,6‐diformylphenol, resulted from hydroxylation of the corresponding isophthalaldehyde derivative. H2L and 1 were characterized by different spectroscopic techniques, and their molecular structures were confirmed by single‐crystal X‐ray diffraction. The reaction of H2L with copper(II) under argon, on the other hand, resulted in a brown diamagnetic solid [Cu2L]·H2O (2) containing copper(I), which was readily transformed into 1 when exposed to air. In contrast, the reaction with [Cu(CH3CN)4][BF4] afforded a mononuclear complex [Cu(H2L)][BF4]·H2O (3), and single crystals of [Cu(H2L)2][BF4] (4) were isolated from its dichloromethane solution. H2L cleaved plasmid DNA in the presence of copper(II) independently of any reducing agent, but more efficiently when ascorbate was present. The cleavage process is likely oxidative because the enzyme catalase, which decomposes hydrogen peroxide, quenched the reaction. In the absence of ascorbate, the ligand H2L presumably acts as the reductant in the redox reaction, as exploited also in the synthesis of 1. As a consequence, a variety of reactive oxygen species were generated, eventually also leading to the cleavage of DNA (“self‐activating” chemical nuclease).

show abstract

Section: Resultssupporting

confidence: 69%

Reaction of a Bis(benzoylhydrazone) with Copper(II): Complex Formation, Hydroxylation, and DNA Cleavage Activity

et al. 2013

View full text Add to dashboard Cite

show abstract

“…Skeletal metal-oxygen and metal-nitrogen vibrations can be assigned from the far IR, 579-556 and 479-429 cm À1 to v(M-O) and v(M-N), respectively [23,24].…”

Section: Ir Spectramentioning

confidence: 99%

Phenoxo-bridged symmetrical homobinuclear complexes derived from an “end-off” compartmental ligand, 2,6- bis [5′-chloro-3′-phenyl- 1H -indole-2′-carboxamidyliminomethyl]-4-methylphenol

Rahaman

Ijare

Jadegoud

et al. 2009

Journal of Coordination Chemistry

View full text Add to dashboard Cite

A compartment ligand 2,6-bis[5 0 -chloro-3 0 -phenyl-1H-indole-2 0 -carboxamidyliminomethyl]-4-methylphenol was prepared and homobinuclear phenol-bridged Cu(II), Ni(II), Co(II), Zn(II), Cd(II), Hg(II), Fe(III), and Mn(II) complexes have been prepared by the template method using the precursors 2,6-diformyl-4-methylphenol, 5-chloro-3-phenylindole-2-carbohydrazide and metal chlorides in 1 : 2 : 2 ratio, respectively. The complexes were characterized by elemental analyses, conductivity measurements, magnetic susceptibility data, IR, NMR, FAB mass and ESR spectra, TGA, and powder XRD data. Cu(II), Co(II), Zn(II), Cd(II) and Hg(II) complexes exhibit square pyramidal geometry whereas Ni(II), Mn(II), and Fe(III) complexes are octahedral. Low magnetic moment values for Cu(II), Ni(II), Co(II), Fe(III), and Mn(II) complexes show antiferromagnetic spin-exchange interaction between two metal centers in binuclear complexes. The ligand and its complexes were tested for antibacterial activity against Escherichia coli and Staphyloccocus aureus, and antifungal activity against Aspergillus niger and Candida albicans.

show abstract

“…An E configuration with respect to the N-N bond is observed, with a C-N-N-C torsion angle of À176.6 (2) . The C1-O1 and C3-O2 distances are 1.233 (3) and 1.226 (2) Å , respectively, typical of double bonds (Sakarnoto et al, 1989;Yan et al, 1993). The C3-N2, C1-N1 and N1-N2 bond distances are typical for a single bond, at 1.331 (3), 1.328 (3) and 1.384 (3) Å , respectively, and these are in agreement with the values found in the analogous compound, N 0 -(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide (Galić et al, 2001).…”

mentioning

confidence: 96%

2′-Acetyl-2-hydroxynaphthohydrazide

Zhao

Dou

et al. 2006

Acta Cryst E

View full text Add to dashboard Cite

The title compound, C13H12N2O3, has been synthesized and characterized by X‐ray diffraction and FT–IR spectroscopic analysis. The approximately planar molecule is in an E configuration with respect to the N—N bond [torsion angle −176.6 (2)°]. In the crystal structure, each hydrazide adopts the ketoamine form to link adjacent molecules by the maximum possible number of O—H⋯O and N—H⋯O intermolecular hydrogen bonds. A one‐dimensional chain framework is formed by this hydrogen bonding.

show abstract

Crystal structures and magnetic properties of bi- and tetra-nuclear copper(II) complexes of 2,6-diformyl-4-methylphenol di(benzoylhydrazone)

Cited by 37 publications

References 1 publication

Reaction of a Bis(benzoylhydrazone) with Copper(II): Complex Formation, Hydroxylation, and DNA Cleavage Activity

Reaction of a Bis(benzoylhydrazone) with Copper(II): Complex Formation, Hydroxylation, and DNA Cleavage Activity

Phenoxo-bridged symmetrical homobinuclear complexes derived from an “end-off” compartmental ligand, 2,6- bis [5′-chloro-3′-phenyl- 1H -indole-2′-carboxamidyliminomethyl]-4-methylphenol

2′-Acetyl-2-hydroxynaphthohydrazide

Contact Info

Product

Resources

About