Ni(salicylaldehyde thiosemicarbazone(-2H))(4,4'-bipyridine) | 936740-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Ni(salicylaldehyde thiosemicarbazone(-2H))(4,4'-bipyridine)
• 英文别名: (Ni(2-hydroxybenzaldehyde thiosemicarbazone-2H))2(4,4'-bipyridine)；(Ni(2-hydroxybenzaldehyde thiosemicarbazone-2H))2(bipy)；2-[(E)-carbamothioylazanidyliminomethyl]phenolate;nickel(2+);4-pyridin-4-ylpyridine
• CAS: 936740-85-1
• 化学式: C₂₆H₂₂N₈Ni₂O₂S₂
• 分子量: 660.025
• InChiKey: YYBCFXMONOOAIR-UHFFFAOYSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  40
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  215
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4,4'-联吡啶 、 Ni2(salicylaldehyde thiosemicarbazone(-2H))2 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到Ni(salicylaldehyde thiosemicarbazone(-2H))(4,4'-bipyridine)
  参考文献：
  名称：

  Nickel complexes of some thiosemicarbazones: Synthesis, structure, catalytic properties and cytotoxicity studies

  摘要：

  Reaction of salicylaldehyde thiosemicarbazone (H2L1), 2-hydroxyacetophenone thiosemicarbazone (H2L2) and 2-hydroxynaphthaldehyde thiosemicarbazone (H2L3) with Ni(ClO4)(2)center dot 6H(2)O afforded dimeric complexes of type [{Ni(L)} 2]. Reaction of these complexes with triphenylphosphine (PPh3), pyridine (py) and 4,4'-bipyridine (bpy) has yielded complexes of type [Ni(L)(PPh3)], [Ni(L)(py)] and [{Ni(L)}(2)(bpy)], respectively, which have also been obtained from reaction of the thiosemicarbazones with Ni(ClO4)2 center dot 6H(2)O and PPh3 or pyridine or 4,4'-bipyridine. Structures of the [{Ni(L)}(2)] complexes have been optimized by DFT calculations. Crystal structures of [Ni(L-2)(PPh3)], [Ni(L-2)(py)] and [{Ni(L-1)}(2)(bpy)] have been determined. In all these complexes thiosemicarbazone is coordinated to nickel as ONS-donor. All these complexes show characteristic H-1 NMR spectra and intense absorptions in the visible and ultraviolet region. Cyclic voltammetry on the complexes shows one irreversible oxidation on the positive side of SCE, and one irreversible reduction on the negative side. The mixed-ligand nickel complexes are found to be efficient catalysts for Heck type C-C coupling reactions. In vitro cytotoxicity screenings of the six mononuclear nickel complexes have been also carried out in a human tumor cell lines, viz. breast carcinoma cell line (MCF-7). [Ni(L-3)(py)] shows the lowest LD50 value. An apoptosis study in MCF-7 with all the complexes confirms that at concentrations near LD50 they induce apoptosis. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.034

文献信息

• Synthesis, structure, sorption and magnetic properties of Ni(II) and Cu(II) complexes with thiosemicarbazone of 2-hydroxybenzaldehyde, bridged by 4,4′-bipyridine
  作者：Sergey V. Kolotilov、Olivier Cador、Stéphane Golhen、Oleksiy Shvets、Vladimir G. Ilyin、Vitaly V. Pavlishchuk、Lahcène Ouahab

  DOI：10.1016/j.ica.2006.09.025

  日期：2007.4

  (ML)(2)(bipy) complexes (LH2 = thiosemicarbazone of 2-hydroxybenzaldehyde, bipy = 4,4'-bipyridine, M = Ni(II), 1, or Cu(II), 2) were synthesized and characterized by X-ray crystallography. Compound 1 possessed porous structure due to peculiarities of crystal packing, whereas 2 formed infinite zig-zag chains with dense non-porous packing. It was shown that 1 absorbed 0.013 cm(3)/g of methanol vapor in two steps. Complex 1 was diamagnetic; for 2, the dependency of chi versus T could be interpreted by Bleaney-Bowers expression in 20-300 K temperature range (J = -6.8 cm(-1), g = 2.07). (C) 2006 Elsevier B.V. All rights reserved.