(4)N-phenyl-2-[1-(pyrrol-2-yl)ethylidene]-hydrazine carbothioamide | 381224-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (4)N-phenyl-2-[1-(pyrrol-2-yl)ethylidene]-hydrazine carbothioamide
• 英文别名: 2-acetylpyrrole-N-phenylthiosemicarbazone
• CAS: 381224-97-1
• 化学式: C₁₃H₁₄N₄S
• 分子量: 258.347
• InChiKey: VADWWAVGLDDFES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.21
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4)N-phenyl-2-[1-(pyrrol-2-yl)ethylidene]-hydrazine carbothioamide 、 trans-bis(triphenylphosphine)palladium dichloride 在 N(C₂H₅)3 作用下， 以 乙腈 为溶剂， 以71%的产率得到Pd(κ3-C4,N3,S-2-acetylpyrrole-N-phenylthiosemicarbazonato)
  参考文献：
  名称：

  Thiosemicarbazonates of palladium(II): The presence of methyl/phenyl substituents (R2) at C2 carbon atom induces C–H activation of R1 rings of thiosemicarbazones {R1R2C2N3–N2H–C1(S)–N1HR3}

  摘要：

  A series of palladium(II) complexes involving C-H and N-H bond activations of the R-1 rings of thiosemicarbazones {R-1(R-2)C-2-N-3-N-2(H)-C-1(=S)-(NHR3)-H-1; R-1, R-2: thiopheneyl, Me, H2L1 (R-3 = Me), H2L2 (R-3 = Ph); R-1, R-2: Ph, Me, H2L3 (R-3 = Me), H2L4 (R-3 = Ph); R-1, R-2: Ph, Ph, H2L5 (R-3 = Me), H2L6 (R-3 = Ph) and R-1, R-2: pyrrole, Me, H2L7 (R-3 = Me), H2L8 (R-3 = Ph)} are described. Methyl group (R-2) at C-2 carbon in H2L1 and H2L2 induced C-H bond activation of the thiopheneyl ring and formed cyclometallated complexes, [Pd(kappa(3)-C-4,N-3,S-L)(PPh3)] (L - L-1, 1; L-2, 2). Similarly, phenyl rings (R-1) in H2L3, H2L4, H2L5, H2L6 at C-2 carbon have shown C-H activations forming cyclometallated complexes, [Pd(kappa(3)-C-4,N-3, S-L)(PPh3)] (L = L-3, 3; L-4, 4; L-5, 5; L-6, 6). However, pyrrole ring did not exhibit similar C-H activation behavior, rather involved N-H activation and formed complexes, [Pd(kappa(3)-N-4,N-3, S-L)(PPh3)] {L = L-7, 7; L-8, 8}. All these complexes have been characterized with the help of analytical data, spectroscopic techniques (IR, H-1 and P-31 NMR), and single crystal X-ray crystallography (1, 2, 4, 5, 7 and 8). The thiosemicarbazone ligands behave as dinegative C-4, N-3, S-chelating in 1-6 and N-4, N-3, S-chelating in complexes 7 and 8. Interestingly, complexes 2, 4 and 8, with phenyl substituent at N-1 atom, have two independent molecules in their respective crystal lattices. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.11.028

文献信息

• Group 12 Metal Complexes of 2-Formylpyrrole-(4PL₁) and 2-Acetylpyrrole-N(4)-phenylthiosemicarbazone (4Pl₂), as Examples form Different Donor Modes. Crystal and Molecular Structures of [Hg(4PL₁- H)Br]₂ and [Zn(4PL₂)₂Br₂] · 2 EtOH
  作者：Rosa Carballo、Alfonso Castiñeiras、Teresa Pérez

  DOI：10.1515/znb-2001-0904

  日期：2001.9.1

  The reactions of ⁴N-phenyl-2-[ 1 -(pyrrol-2-yl)methylidene]-hydrazine carbothioamide (4PL₁) and ⁴N-phenyl-2-[l-(pyrrol-2-yl)ethylidene]-hydrazine carbothioamide (4PL₂) with Group 12 metal halides afford complexes of types [M(L)₂X₂] [M = Zn, L = 4PL₁ or 4PL₂, X = Cl, Br or I; M = Cd, L = 4PL₁, and X = Cl, or L = 4PL₂ and X = Cl, Br or I] and [M(L)X₂] [M = Cd, L = 4PL₁, X = Br or I; M = Hg, L = 4PL₁ or 4PL₂, X = Cl, Br or I]. The new compounds were characterized by elemental analysis, FAB mass spectrometry, IR spectroscopy, and, in the case of sufficiently soluble compounds, ¹H, ¹³C and, when appropriate, ¹¹³Cd or ¹⁹⁹Hg NMR spectrometry. The structures of [Hg(4PL₁-H)Br] and [Zn(4PL₂)₂Br₂] · 2 EtOH were also studied by single-crystal X-ray diffractometry. In [Hg(4PL₁-H)Br] crystallized from the mother liquor of its synthesis, 4PL₁ behaves as a monodeprotonated S,N-bidentate ligand. Otherwise, with Hg(II), Zn(II) and Cd(II), 4PL₁ and 4PL₂ both behave as neutral S-monodentate ligands.

  摘要：对4N-苯基-2-[1-(吡咯-2-基)甲基亚胺基]硫代甲酰肼（4PL1）和4N-苯基-2-[1-(吡咯-2-基)乙基亚胺基]硫代甲酰肼（4PL2）与12族金属卤化物的反应得到了类型为[M(L)2X2]（M = Zn，L = 4PL1或4PL2，X = Cl，Br或I；M = Cd，L = 4PL1，X = Cl，或L = 4PL2，X = Cl，Br或I）和[M(L)X2]（M = Cd，L = 4PL1，X = Br或I；M = Hg，L = 4PL1或4PL2，X = Cl，Br或I）的配合物。新化合物通过元素分析、FAB质谱、红外光谱以及在溶解度足够的化合物中的1H、13C和适当情况下的113Cd或199Hg核磁共振光谱进行了表征。[Hg(4PL1-H)Br]和[Zn(4PL2)2Br2]·2乙醇的结构也通过单晶X射线衍射学进行了研究。在从合成母液中结晶的[Hg(4PL1-H)Br]中，4PL1表现为一种单去质子的S，N-双齿配体。否则，对于Hg(II)，Zn(II)和Cd(II)，4PL1和4PL2均表现为中性S-单齿配体。