Synthesis, Structural Characteristics and Biological Activities of Complexes of ZnII, CdII, HgII, PdII, and PtII with 2-Acetylpyridine 4-Methylthiosemicarbazone

Bermejo, Elena; Carballo, Rosa; Castiñeiras, Alfonso; Domínguez, Ricardo; Liberta, Anthony E.; Maichle‐Mößmer, Cäcilia; Salberg, Michelle M.; West, Douglas X.

doi:10.1002/(sici)1099-0682(199906)1999:6<965::aid-ejic965>3.0.co;2-a

Cited by 70 publications

(38 citation statements)

References 46 publications

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“…These IR spectra of the zinc(II), cadmium(II), and mercury(II) complexes exhibit three bands between 3470Ϫ3340, 3330Ϫ3290 and 3210Ϫ3100 cm Ϫ1 due to the presence of the amino and imino groups. In all complexes the shift of the thiocarbonyl stretching mode (861 cm Ϫ1 in HAmpip) to lower frequencies is in accord with coordination through the sulfur atom [21], whereas the strong bands appearing at approximately 1590±10 cm Ϫ1 may be assigned to ν(CϭN) vibrations (1601 cm Ϫ1 in HAmpip) and point towards the coordinated azomethine groups [22]. The expected shifts of the pyridine bands, indicating coordination of the nitrogen atom, is less evident, since the 1600Ϫ1400 cm Ϫ1 region is complicated by the presence of thioamide bands.…”

Section: Spectral Studiesmentioning

confidence: 64%

Coordination of ZnII, CdII, and HgII by 2-Pyridineformamide-3-piperidyl-thiosemicarbazone

Castiñeiras

García

Bermejo

et al. 2002

Z. anorg. allg. Chem.

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Sodium in dry methanol reduces 2-cyanopyridine in the presence of 3-piperidylthiosemicarbazide and produces 2-pyridineformamide-3-piperidylthiosemicarbazone, HAmpip. Complexes with zinc(II), cadmium(II), and mercury (II) have been prepared and characterized by elemental analyses and spectroscopic techniques. In addition, the crystal structures of [Zn(Ampip) 2 ], [Zn(Ampip)(Oac)] 2 , [Cd(HAmpip)Cl 2 ]·(CH 3 ) 2 SO, [Cd(HAmpip)Br 2 ] · (CH 3 ) 2 SO, [Cd(HAmpip)I 2 ]·(CH 3 ) 2 SO, [Cd(Ampip) 2 ]and [Hg(HAmpip)Br 2 ]·(CH 3 ) 2 SO have been solved. Coordination of the anionic and neutral thiosemicarbazone ligand is via the pyridyl nitrogen, imine nitrogen and thiolato/thione sulfur atom,

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Section: Spectral Studiesmentioning

confidence: 64%

Coordination of ZnII, CdII, and HgII by 2-Pyridineformamide-3-piperidyl-thiosemicarbazone

Castiñeiras

García

Bermejo

et al. 2002

Z. anorg. allg. Chem.

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“…4). The Zn±I and Zn±S distances in 3 are within the normal range for [ZnS 2 I 2 ] kernels [21,22], and the Cd±Br and Cd±S distances in 5 are likewise similar to those of bromo complexes of other thiosemicarbazones acting as S-monodentate [23] or N,N,S-tridentate [24,25] ligands. In 7, the Hg±S distance and the distance between the mercury and non-bridging Cl atom are slightly shorter than in complexes of mercury chloride with N,S-didentate [26] or N,N,S-tridentate [24,25,27] thiosemicarbazones, but are similar to those found in other dimeric mercury chloride complexes with S-monodentate thiosemicarbazone ligands [28,29].…”

Section: Molecular Structuresmentioning

confidence: 84%

“…The Zn±I and Zn±S distances in 3 are within the normal range for [ZnS 2 I 2 ] kernels [21,22], and the Cd±Br and Cd±S distances in 5 are likewise similar to those of bromo complexes of other thiosemicarbazones acting as S-monodentate [23] or N,N,S-tridentate [24,25] ligands. In 7, the Hg±S distance and the distance between the mercury and non-bridging Cl atom are slightly shorter than in complexes of mercury chloride with N,S-didentate [26] or N,N,S-tridentate [24,25,27] thiosemicarbazones, but are similar to those found in other dimeric mercury chloride complexes with S-monodentate thiosemicarbazone ligands [28,29]. Of the distances between the mercury atom and bridging chlorine atoms, the shortest two are significantly shorter than in other chloro-bridged Hg dimers with S-monodentate ligands [28,32], while the longest two are at least 0.2 A Ê longer than in any other known dimer of this kind [28,30,31] (in those with long Hg±Cl br distances most closely approaching those of 7 the mercury atoms have coordination number five, like 7 [32]).…”

Section: Molecular Structuresmentioning

confidence: 84%

“…In the spectra of 10±13 coordination via the azomethine nitrogen atom is suggested by the appearance of a new band attributable to m(M±N) near 350 cm ±1 . The metal-halogen stretching bands have been identified on the basis of the literature [35,36] and in view of the ratios m(M±Br)/ m(M±Cl) = 0.74±0.77 and m(M±I)/m(M±Cl) = 0.65 that hold in other cases [23,24,28,37].…”

Section: Infrared Spectramentioning

confidence: 99%

“…M. p. (°C) 297. C 16 H24 N 8 OPdS 2 (514.97): calcd. C 37.3, H 4.7, N 21.8, S 12.5; found C 37.8, H 4.6, N 21.4, S 12.9%.…”

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Synthesis and Structural Characterization of Metal Complexes of 2-Formylpyrrole-4N-ethylthiosemicarbazone (4 EL1) and 2-Acetylpyrrole-4N-ethylthiosemicarbazone (4 EL2)

Bermejo¹,

Castiñeiras²,

Pérez³

et al. 2001

Z. anorg. allg. Chem.

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The reactions of 4 N-ethyl-2-[1-(pyrrol-2-yl)methylidene(hydrazine carbothioamide (4 EL 1 ) and 4 N-ethyl-2-[1-(pyrrol-2-yl)ethylidene(hydrazine carbothioamide (4 EL 2 ) with Group 12 metal halides afforded complexes of types [M(L) 2 X 2 ] (M = Zn, Cd; L = 4 EL 1 , 4 EL 2 ; X = Cl, Br, I; 1±6, 14±19) and [M(L)X 2 ] (M = Hg; L = 4 EL 1 , 4 EL 2 ; X = Cl, Br, I; 7±9, 20±22). In addition, reaction of 4 EL 1 with salts of Cu II , Ni II , Pd II and Pt II afforded compounds of type [M(4 EL 1 ±H) 2 ] (10±13). The new compounds were characterized by elemental analysis, FAB mass spectrometry, IR and electronic spectroscopy and, for sufficiently soluble compounds, 1 H, 13 C and, when appropriate, 113 Cd or 199 Hg NMR spectrometry. The spectral data suggest that in their complexes with Group 12 metal cations, both thiosemicarbazones are neutral and S-monodentate; and for [Zn(4 EL 1 ) 2 I 2 ](3), [Cd(4 EL 1 ) 2 Br 2 ] (5) and [Hg(4 EL 1 )Cl 2 ] 2 (7) this was confirmed by X-ray diffractometry. By contrast, in its complexes with Cu II and Group 10 metal cations, 4 EL 1 is monodeprotonated and S,N-bidentate, as was confirmed by X-ray diffractometry for [Ni(4 EL 1 ±H) 2 ] (11) and [Pd(4 EL 1 ±H) 2 ] (12).Synthese und Strukturelle Charakterisierung von Metall-Komplexen von 2-Formylpyrrol-4 N-ethylthiosemicarbazon (4 EL 1 ) und 2-Acetylpyrrol-4 N-ethylthiosemicarbazon (4 EL 2 ) Inhaltsu È bersicht. Die Reaktionen von 4 N-ethyl-2-[1-(pyrrol-2-yl)methyliden(hydrazin-carbothioamid (4 EL 1 ) und 4 Nethyl-2-[1-(pyrrol-2-yl)ethyliden(hydrazin-carbothioamid (4 EL 2 ) mit Halogeniden der Metalle der 12. Gruppe ergeben Komplexe des Typs [M(L) 2 X 2 ] (M = Zn, Cd; L = 4 EL 1 , 4 EL 2 ; X = Cl, Br, I; 1±6, 14±19) und [M(L)X 2 ] (M = Hg; L = 4 EL 1 , 4 EL 2 ; X = Cl, Br, I; 7±9, 20±22). Auûerdem fu È hrt die Reaktion von 4 EL 1 mit Salzen von Cu II , Ni II , Pd II und Pt II zu Verbindungen des Typs [M(4 EL 1 ±H) 2 ] (10±13). Die neuen Verbindungen wurden durch Elementaranalysen, FAB-Massenspektren sowie IR-und Elektronenspektren charakterisiert. Von den ausreichend lo È slichen Verbindungen wurden auûerdem 1 H-, 13 C-und bei den Cd-und Hg-Verbindungen auch die 113 Cd-oder 199 Hg-NMR-Spektren registriert. Die spektroskopischen Daten deuten darauf hin, daû die Thiosemicarbazon-Einheiten, 4 EL 1 , in den Komplexen der Kationen der 12. Gruppe als ungeladene Liganden vorliegen, die u È ber das S-Atom einza È hnig gebunden sind. Fu È r die Komplexe [Zn(4 EL 1 ) 2 I 2 ] (3), [Cd(4 EL 1 ) 2 Br 2 ] (5) und [Hg(4 EL 1 )Cl 2 ] 2 (7) wird dieser Befund durch Kristallstrukturanalysen bewiesen. Im Gegensatz dazu sind die Liganden 4 EL 1 in den Komplexen von Cu II und den Metallkationen der 10. Gruppe einfach deprotoniert und zweiza È hnig u È ber S,N gebunden, wie auch durch Kristallstrukturanalysen von [Ni(4 EL 1 ±H) 2 ] (11) and [Pd(4 EL 1 ±H) 2 ] (12) belegt wird.

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Selective oxidation of olefins and aromatic alcohols with tert‐butylhydroperoxide catalyzed by polymer‐anchored transition‐metal complexes

Roy

Mondal

et al. 2011

J of Applied Polymer Sci

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Three polymer-anchored metal complexes (Co, Cu, and Pd) were synthesized and characterized. The catalytic performance of these complexes was tested for the oxidation of olefins and aromatic alcohols. These complexes showed excellent catalytic activity and high selectivity. These complexes selectively gave epoxides and aldehydes from olefins and alcohols, respectively. Individually, the effect of various solvents, oxidants, substrate oxidant molar ratios, temperatures, and catalyst amounts for the oxidation of cyclohexene and benzyl alcohol were studied. Under optimized reaction conditions, 96, 81, and 71% conversions of cyclohexene and 86, 79, and 73% conversions of benzyl alcohol were obtained with Co(II), Cu(II), and Pd(II) catalysts, respectively. The catalytic results reveal that these complexes could be recycled more than five times without much loss in activity.

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Synthesis, Structural Characteristics and Biological Activities of Complexes of ZnII, CdII, HgII, PdII, and PtII with 2-Acetylpyridine 4-Methylthiosemicarbazone

Cited by 70 publications

References 46 publications

Coordination of ZnII, CdII, and HgII by 2-Pyridineformamide-3-piperidyl-thiosemicarbazone

Coordination of ZnII, CdII, and HgII by 2-Pyridineformamide-3-piperidyl-thiosemicarbazone

Synthesis and Structural Characterization of Metal Complexes of 2-Formylpyrrole-4N-ethylthiosemicarbazone (4 EL1) and 2-Acetylpyrrole-4N-ethylthiosemicarbazone (4 EL2)

Selective oxidation of olefins and aromatic alcohols with tert‐butylhydroperoxide catalyzed by polymer‐anchored transition‐metal complexes

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