1,3-bis-(2′-benzimidazolylimino)isoindoline | 20102-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1,3-bis-(2′-benzimidazolylimino)isoindoline
• 英文别名: 1,3-bis(benzimidazol-2-ylimino)isoindoline；bis(2-benzimidazolylimino)isoindoline；N,N-bis-(1H-benzoimidazol-2-yl)-isoindole-1,3-diylidenediamine
• CAS: 20102-70-9
• 化学式: C₂₂H₁₅N₇
• 分子量: 377.408
• InChiKey: HEYBKKRWMNXZFX-UHFFFAOYSA-N

物化性质

• 沸点：
  734.2±43.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.11
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-bis-(2′-benzimidazolylimino)isoindoline 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 Fe^III(1,3-bis-(2′-benzimidazolylimino)isoindolinate)(catecholate)
  参考文献：
  名称：

  子午线配体的铁（III）配合物作为内二醇裂解邻苯二酚双加氧酶的功能模型。

  摘要：

  1,3-双（2'-芳基）异吲哚啉（BAIH）与各种N-给体芳基的六种二氯铁（III）配合物已通过光谱（红外，紫外可见），电化学（循环伏安法），微分析，以及两种情况下的X射线晶体学分析。Fe III Cl 2（L n）配合物的结构特征（n = 3，L 3 = 1,3-双（2'-噻唑基亚氨基）异吲哚啉，n = 5，L 5＝ 1，3-双（4-甲基-2′-哌啶基亚氨基）异吲哚啉是五配位的三角双锥体，异吲哚啉配体在子午线上占据两个轴向和一个赤道位置。这些化合物用作儿茶酚双加氧酶模型的前体，该模型是在添加3,5-二叔丁基邻苯二酚（H 2 DBC）和过量的三乙胺后在溶液中形成的。这些加合物与N，N中的双氧反应-二甲基甲酰胺，以及通过色谱和质谱法对产物的分析显示出较高的内部二醇相对于额外的二醇选择性（内部二醇/雌二醇产物的比率在46.5至6.5之间变化）。通过跟踪儿茶酚酸到铁配体到金属的电荷转移（LMCT

  DOI：

  10.1021/ic302378r

文献信息

• Binding a meridional ligand in a facial geometry: A square peg in a round hole
  作者：Briana R. Schrage、Dominick Vitale、Kimberly A. Kelly、Victor N. Nemykin、Richard S. Herrick、Christopher J. Ziegler

  DOI：10.1016/j.jorganchem.2020.121331

  日期：2020.7

  bis(pyridylimino)isoindoline (BPI) ligand is a tridentate chelate that binds to metals via a meridional coordination mode. However, when this ligand forms a complex with Re(CO)3, an almost exclusively facial moiety, the BPI ligand deforms to coordinate in a facial mode. We have investigated this deformation via structural and theoretical means, and the non-planar binding mode of the ligand bathochromically shifts

  双（吡啶亚氨基）异二氢吲哚（BPI）配体是一种三齿螯合物，通过经向配位模式与金属结合。然而，当该配体与 Re(CO) 3（几乎完全是面部部分）形成复合物时，BPI 配体会变形以在面部模式下配位。我们通过结构和理论手段研究了这种变形，配体的非平面结合模式使金属向配体电荷转移 (MLCT) 转变。
• Correlation between the SOD-like activity of hexacoordinate iron(II) complexes and their Fe3+/Fe2+ redox potentials
  作者：Balázs Kripli、Gábor Baráth、É. Balogh-Hergovich、Michel Giorgi、A. Jalila Simaan、László Párkányi、József S. Pap、József Kaizer、Gábor Speier

  DOI：10.1016/j.inoche.2010.10.023

  日期：2011.1

  Abstract Hexacoordinate, high-spin iron(II) complexes with different isoindoline-derivative ligands have been prepared and characterized. The Fe3+/Fe2+ redox transition is reversible in each case, but the E1/2 values vary in a ~ 400 mV range depending on the ligand. SOD-like activity of the complexes was determined by indirect methods with cytochrome c, and nitroblue tetrazolium indicator at pH 7.6

  摘要 已制备并表征了具有不同异二氢吲哚衍生物配体的六配位高自旋铁 (II) 配合物。Fe3+/Fe2+ 氧化还原转变在每种情况下都是可逆的，但 E1/2 值在 ~ 400 mV 范围内变化，具体取决于配体。复合物的 SOD 样活性通过间接方法用细胞色素 c 和硝基四唑指示剂在 pH 7.6 下测定。测量的活性与 Fe3+/Fe2+ 对的氧化还原电位相关。结果表明超氧化物歧化是通过铁位点的内球机制发生的。
• Transition metal catalysts for olefin polymerization
  申请人：——

  公开号：US20030065113A1

  公开（公告）日：2003-04-03

  A catalyst system useful for polymerizing olefins is disclosed. It comprises an activator and an organometallic complex. The complex includes a Group 3-10 transition or lanthanide metal and a 1,3-bis(arylimino)isoindoline or 1,3-bis(heteroarylimino)isoindoline ligand. Activities of the Group 8-10 catalyst systems rival or exceed those of late transition metal bis(imines). The resulting polyolefins typically have high molecular weights, broad molecular weight distributions, and a high degree of crystallinity, which makes them valuable for film applications.

  本发明揭示了一种用于聚合烯烃的催化剂系统。它包括一个活化剂和一个有机金属配合物。该配合物包括一个3-10族过渡金属或镧系金属和一个1,3-双(芳基亚胺)异吲哚啉或1,3-双(杂芳基亚胺)异吲哚啉配体。8-10族催化剂系统的活性可与晚期过渡金属双亚胺相媲美甚至超越。由此产生的聚烯烃通常具有高分子量，广泛的分子量分布和高结晶度，这使它们在薄膜应用中非常有价值。
• Tetra-, penta- and hexacoordinate copper(II) complexes with N3 donor isoindoline-based ligands: Characterization and SOD-like activity
  作者：József S. Pap、Balázs Kripli、Vanda Bányai、Michel Giorgi、László Korecz、Tamás Gajda、Dávid Árus、József Kaizer、Gábor Speier

  DOI：10.1016/j.ica.2011.06.001

  日期：2011.10

  Reaction of 1,3-bis(2'-Ar-imino)isoindolines (HLn, n = 1-7, Ar = benzimidazolyl, N-methylbenzimidazolyl, thiazolyl, pyridyl, 3-methylpyridyl, 4-methylpyridyl, and benzthiazolyl, respectively) with Cu(OCH3)(2) yields mononuclear hexacoordinate complexes with Cu(L-n)(2) composition. With cupric perchlorate square-pyramidal [Cu-II(HLn)(NCCH3)(OClO3)]ClO4 complexes (n = 1, 3, 4) were isolated as perchlorate salts, whereas with chloride Cu-II(HLn)Cl-2 (n = 1, 4), or square-planar (CuCl2)-Cl-II(HLn) (n = 2, 3, 7) complexes are formed. The X-ray crystal structures of Cu(L-3)(2), Cu(L-5)(2), [Cu-II(HL4)(NCCH3)(OClO3)]ClO4, (CuCl)-Cl-II(L-2) and (CuCl)-Cl-II(L-7) are presented along with electrochemical and spectral (UV-Vis, FT-IR and X-band EPR) characterization for each compound. When combined with base, the isoindoline ligands in the [Cu-II(HLn)(NCCH3)(OClO3)]ClO4 complexes undergo deprotonation in solution that is reversible and induces UV-Vis spectral changes. Equilibrium constants for the dissociation are calculated. X-band EPR measurements in frozen solution show that the geometry of the complexes is similar to the corresponding X-ray crystallographic structures. The superoxide scavenging activity of the compounds determined from the McCord-Fridovich experiment show dependence on structural features and reduction potentials. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis, structure, and catalase-like activity of a novel manganese(II) complex: Dichloro[1,3-bis(2′-benzimidazolylimino)isoindoline]manganese(II)
  作者：József Kaizer、Balázs Kripli、Gábor Speier、László Párkányi

  DOI：10.1016/j.poly.2009.01.008

  日期：2009.4

  Reaction of the ligand 1,3-bis(2'-benzimidazolylimino)isoindoline with manganese(II) chloride in acetonitrile/methanol leads to the novel mononuclear manganese(II) complex 1,3-bis(2'-benzimidazolylimino)isoindolinedichloro manganese(II) [Mn(bimindH)Cl-2], which has been characterized by various techniques such as elemental analysis, IR, UV-Vis, ESR spectroscopy. and X-ray diffraction. The ligand bimindH was synthesized by fusing phthalonitrile and 2-aminobenzimidazole at high temperature until ammonia evolution ceased. The catalase-like activity of the complex was tested in propionitrile, and it proved to be active in the dihydrogen peroxide dismutation. Based on kinetic studies the reaction is first-order in relation to both the complex and hydrogen peroxide. (C) 2009 Elsevier Ltd. All rights reserved.