Preparation, Structural Characterization, and Antifungal Activities of Complexes of Group 12 Metals with 2-Acetylpyridine- and 2-Acetylpyridine-N-oxide-4N-phenylthiosemicarbazones

Bermejo, Elena; Castiñeiras, Alfonso; Domínguez, Ricardo; Carballo, Rosa; Maichle‐Mößmer, Cäcilia; Strähle, Joachim; West, Douglas X.

doi:10.1002/(sici)1521-3749(199906)625:6<961::aid-zaac961>3.0.co;2-j

Cited by 41 publications

(38 citation statements)

References 21 publications

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“…The distances and bond angles of both thiosemicarbazone arms are very similar, and the molecular conformation of the atoms and the azomethine nitrogen atoms N(6) and N(3) is cis with respect to the C(4)−N(5) and C(1)−N(2) bonds. The N−N distances are shorter than 1.44 Å, accepted as typical for a single N−N bond, and agree well with those of similar thiosemicarbazones . C−S bonds distances are intermediate between those of single and double bond (1.82 and 1.56, respectively), showing the partial double bond character implied by the canonical structures usually considered for thiosemicarbazones.…”

Section: Resultssupporting

confidence: 77%

Versatile Chelating Behavior of Benzil Bis(thiosemicarbazone) in Zinc, Cadmium, and Nickel Complexes

et al. 2004

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Reactions of benzil bis(thiosemicarbazone), LH(6), with M(NO(3))(2).nH(2)O (M = Zn, Cd, and Ni), in the presence of LiOH.H(2)O, show the versatile behavior of this molecule. The structure of the ligand, with the thiosemicarbazone moieties on opposite sides of the carbon backbone, changes to form complexes by acting as a chelating molecule. Complexes of these metal ions with empirical formula [MLH(4)] were obtained, although they show different molecular structures depending on their coordinating preferences. The zinc complex is the first example of a crystalline coordination polymer in which a bis(thiosemicarbazone) acts as bridging ligand, through a nitrogen atom, giving a 1D polymeric structure. The coordination sphere is formed by the imine nitrogen and sulfur atoms, and the remaining position, in a square-based pyramid, is occupied by an amine group of another ligand. The cadmium derivative shows the same geometry around the metal ion but consists of a dinuclear structure with sulfur atoms acting as a bridge between the metal ions. However, in the nickel complex LH(6) acts as a N(2)S(2) ligand yielding a planar structure for the nickel atom. The ligand and its complexes have been characterized by X-ray crystallography, microanalysis, mass spectrometry, IR, (1)H, and (13)C NMR spectroscopies and for the cadmium complex by (113)Cd NMR in solution and in the solid state.

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Section: Resultssupporting

confidence: 77%

Versatile Chelating Behavior of Benzil Bis(thiosemicarbazone) in Zinc, Cadmium, and Nickel Complexes

et al. 2004

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“…The C8 S1 and C8ÐN2 and C8ÐN3 bond distances (Table 1) are close to C S double bonds and CÐN single bonds in thiosemicarbazones (Usman et al, 2002;Chattopadhyay et al, 1988;Latheef et al, 2006) and con®rm the thione form for (I). The C8 S1 bond length of (I) is in agreement with its di-2-pyridyl (Suni et al, 2006), 2-acetylpyridine (Bermejo et al, 1999) and acetophenone (Jian et al, 2005) counterparts, but is less than the 1.688 2…”

Section: Commentsupporting

confidence: 71%

2-Hydroxyacetophenone 4-phenylthiosemicarbazone

Seena¹,

Manoj²,

Kurup³

2006

Acta Crystallogr C

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“…HApT, HAp4mT, HAp4pT) intramolecular H-bonding stabilises both the E thione and Z thione forms; N 1 ◊ ◊ ◊ HN 3 for the Z form and N 2 ◊ ◊ ◊ HN 4 in all cases. 6, 19 The corresponding tautomers, ZE thiol and ZZ thiol, are expected to be unimportant once the N 1 ◊ ◊ ◊ HN 3 Hbonding is lost, despite the possible existence of a new N 2 ◊ ◊ ◊ HS interaction. Summarising, even though six different forms of the TSC ligands studied could be present in solution, only some of them are expected to be observable once thermodynamic equilibrium conditions are attained.…”

Section: Ligand Isomeric Distribution In Solutionmentioning

confidence: 99%

Biologically active thiosemicarbazone Fe chelators and their reactions with ferrioxamine B and ferric EDTA; a kinetic study

et al. 2012

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The Fe III abstraction from Fe III /DFO and Fe III /EDTA complex systems by thiosemicarbazone ligands derived from 2-acetylpyridine has been studied from a kinetico-mechanistic perspective at relevant pH conditions and at varying temperatures and buffer solutions. The reactions have been found to be extremely dependent on the dominant E/Z isomeric form of the TSC ligands present in the reaction medium. Consequently the isomerisation processes occurring on the free ligands have also been monitored under equivalent conditions. The isomerisation process is found to be acid dependent, despite the absence of protonation under the conditions used, and presumably proceeds via an azo-type tautomer of the ligand. In all cases the existence of outer-sphere interaction processes has been established, both promoting the reactions and producing dead-end complexes. has also been conducted with significant differences in the kinetic features that implicate keystone outer-sphere interactions which dominate reactivity, even with isomeric forms that are not the best suited for direct complexation.

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Preparation, Structural Characterization, and Antifungal Activities of Complexes of Group 12 Metals with 2-Acetylpyridine- and 2-Acetylpyridine-N-oxide-4N-phenylthiosemicarbazones

Cited by 41 publications

References 21 publications

Versatile Chelating Behavior of Benzil Bis(thiosemicarbazone) in Zinc, Cadmium, and Nickel Complexes

Versatile Chelating Behavior of Benzil Bis(thiosemicarbazone) in Zinc, Cadmium, and Nickel Complexes

2-Hydroxyacetophenone 4-phenylthiosemicarbazone

Biologically active thiosemicarbazone Fe chelators and their reactions with ferrioxamine B and ferric EDTA; a kinetic study

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