Synthesis, Magnetic Measurements and Spectroscopic Studies of Copper(I) and Copper(II) Complexes of Thiosemicarbazones Derived from Aromatic Aldehydes and Ketones

Akinchan, Naraylan T.; Akinchan, R.; Drożdżewski, Piotr; Yang, Yong Hong; Klein, Tracey L.; West, Douglas X.

doi:10.1080/00945719608004404

Cited by 12 publications

(4 citation statements)

References 15 publications

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“…The ligands benzaldehyde thiosemicarbazone (Hbtsc), furan-2-carbaldehyde thiosemicarbazone (Hftsc), pyridine-2-carbaldehyde thiosemicarbazone (Hpytsc), pyrrole-2-carbaldehyde thiosemicarbazone (Hptsc), and thiophene-2-carbaldehyde thiosemicarbazone (Httsc) were prepared by reported methods. 11 Copper(I) chloride, copper(I) bromide, and copper(I) iodide were prepared by the reduction of CuSO 4 ‚5H 2 O using SO 2 in the presence of NaCl, NaBr or iodide in water. 15 The C, H, and N elemental analyses were obtained with a Carlo Erba 1108 microanalyzer from University of Santiago, Santiago, Spain.…”

Section: Methodsmentioning

confidence: 99%

“…Benzaldehyde, furan-2-carbaldehyde, pyridine-2-carbaldehyde, pyrrole-2-carbaldehyde, thiophene-2-carbaldehyde, and Ph 3 P were procured from Aldrich Sigma Ltd. The ligands benzaldehyde thiosemicarbazone (Hbtsc), furan-2-carbaldehyde thiosemicarbazone (Hftsc), pyridine-2-carbaldehyde thiosemicarbazone (Hpytsc), pyrrole-2-carbaldehyde thiosemicarbazone (Hptsc), and thiophene-2-carbaldehyde thiosemicarbazone (Httsc) were prepared by reported methods . Copper(I) chloride, copper(I) bromide, and copper(I) iodide were prepared by the reduction of CuSO 4 ·5H 2 O using SO 2 in the presence of NaCl, NaBr or iodide in water .…”

Section: Methodsmentioning

confidence: 99%

“…There are only limited reports on the structural chemistry of complexes of thiosemicarbazones with Cu I . [1][2][3][4][5]7,[9][10][11][12][13] The main reason for the lack of copper(I) thiosemicarbazone studies is their insolubility in different organic solvents. Tertiary phosphines are known to play an important role in solubilizing Cu I complexes of heterocyclic thioamides.…”

Section: Introductionmentioning

confidence: 99%

“…The use of copper(II) thiosemicarbazone compounds in biological systems is bound to involve Cu II reduction to Cu I in the cells, and thus the stability of Cu I species is crucial to the hypotoxic reactivity and biological activity of topo-II inhibitors. There are only limited reports on the structural chemistry of complexes of thiosemicarbazones with Cu I . − ,,− The main reason for the lack of copper(I) thiosemicarbazone studies is their insolubility in different organic solvents. Tertiary phosphines are known to play an important role in solubilizing Cu I complexes of heterocyclic thioamides .…”

Section: Introductionmentioning

confidence: 99%

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Bonding Trends of Thiosemicarbazones in Mononuclear and Dinuclear Copper(I) Complexes: Syntheses, Structures, and Theoretical Aspects

et al. 2006

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Reactions of copper(I) halides with a series of thiosemicarbazone ligands (Htsc) in the presence of triphenylphosphine (Ph(3)P) in acetonitrile have yielded three types of complexes: (i) monomers, [CuX(eta1-S-Htsc)(Ph3P)2] [X, Htsc = I (1), Br (2), benzaldehyde thiosemicarbazone (Hbtsc); I (5), Br (6), Cl (7), pyridine-2-carbaldehyde thiosemicarbazone (Hpytsc)], (ii) halogen-bridged dimers, [Cu2(mu2-X)2(eta1-S-Htsc)2(Ph3P)2] [X, Htsc = Br (3), Hbtsc; I (8), furan-2-carbaldehyde thiosemicarbazone (Hftsc); I (11), thiophene-2-carbaldehyde thiosemicarbazone (Httsc)], and (iii) sulfur-bridged dimers, [Cu2X2(mu2-S-Htsc)2(Ph3P)2] [X, Htsc = Cl (4), Hbtsc; Br (9), Cl (10), pyrrole-2-carbaldehyde thiosemicarbazone (Hptsc); Br (12), Httsc]. All of these complexes have been characterized with the help of elemental analysis, IR, 1H, 13C, or 31P NMR spectroscopy, and X-ray crystallography (1-12). In all of the complexes, thiosemicarbazones are acting as neutral S-donor ligands in eta()S or mu2-S bonding modes. The Cu...Cu separations in the Cu(mu2-X)2Cu and Cu(mu2-S)2Cu cores lie in the ranges 2.981(1)-3.2247(6) and 2.813(1)-3.2329(8) Angstroms, respectively. The geometry around each Cu center in monomers and dimers may be treated as distorted tetrahedral. Ab initio density functional theory calculations on model monomeric and dimeric complexes of the simplest thiosemicarbazone [H2C=N-NH-C(S)-NH2, Htsc] have revealed that monomers and halogen-bridged dimers have similar stability and that sulfur-bridged dimers are stable only when halogen atoms are engaged in hydrogen bonding with the solvent of crystallization or H2O molecules.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%