N,N'-bis(5-nitrosalicylidene)-1,2-diaminoethane | 6337-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N'-bis(5-nitrosalicylidene)-1,2-diaminoethane
• 英文别名: N,N’-bis(5-nitrosalicylidene)ethane-1,2-diamine；N,N’-1,2-bis(5-nitrosalicylidine)ethylenediamine；ethylenebis(N,N'-5-nitrosalicylideneimine)；bis-(5-nitro-salicylidene)-ethylenediamine；N,N'-bis(5-nitrosalicylidene)ethane-1,2-diamine；N,N'-bis-(2-hydroxy-5-nitro-benzyliden)-ethylenediamine；N,N'-Bis-(2-hydroxy-5-nitro-benzyliden)-aethylendiamin；N,N'-bis(5-nitrosalicylidene)-1,2-ethylenediimine；n,n'-Bis(5-nitrosalicylidene)ethylenediamine；2-[2-[(2-hydroxy-5-nitrophenyl)methylideneamino]ethyliminomethyl]-4-nitrophenol
• CAS: 6337-28-6
• 化学式: C₁₆H₁₄N₄O₆
• 分子量: 358.31
• InChiKey: YLTXOGYEOSBKDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-bis(5-nitrosalicylidene)-1,2-diaminoethane 在 aq. NaOH 、 air 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Electronic and steric effects in manganese Schiff-base complexes as models for the water oxidation complex in photosystem II. The isolation of manganese-(II) and -(III) complexes of 3- and 3,5-substituted N,N′-bis(salicylidene)ethane-1,2-diamine (H₂salen) ligands

  摘要：

  Manganese-(II) and -(III) complexes of substituted N,N'-bis(salicylidene)ethane-1,2-diamine (H(2)salen) ligands H(2)L (substituents are in the 3,5 or 3,5 positions of the phenyl rings of the salen moiety) have been prepared and thoroughly characterised. The reaction of Mn(ClO4)(2) . 6H(2)O with H(2)L in ethanol in air normally leads to manganese(III) complexes ligated by both the N2O2 ligand and water molecule(s). However, by employing electron-withdrawing substituents on the ligand, e.g. 3-Br,5-NO2, a manganese(II) complex can be obtained. A 'borderline' ligand is represented by the 5-NO2 derivative (nsalen), which produces a manganese(II) complex contaminated with a small amount of a manganese(In) species. Using a more rigorous oxidising agent in the synthesis, [Fe(eta-C5H5)(2)][FeCl4], drives the reaction totally to a manganese(III) complex [Mn(nsalen)Cl(H2O)]. In addition to magnetic susceptibility studies, cyclic voltammetry has been employed. All the complexes exhibit an oxidation and reduction peak, the reversible character being confirmed by pulse voltammetry. Pulse voltammetry also confirmed the nature of the manganese(II) species [Mn(bnsalen)(H2O)(2)]. 2H(2)O [H(2)bnsalen = N,N'-bis(3-bromo-5-nitrosalicylidene)ethane-1,2-diamine] and that a slight amount of a manganese(III) species is present in [Mn(nsalen)(H2O)(2)]. 2H(2)O. Six complexes have been crystallographically characterised. Despite the retention of an octahedral manganese environment in all of them, the supramolecular structures exhibit a wide diversity. The 3,5-dichloro and 5-bromo salen complexes containing co-ordinated water display combined pi and hydrogen bonding, as well as dimerisation. The complex [{Mn(mu-dbsalen)(mu-O)}(2)] (dbsalen = 3,5-dibromo derivative) offers an alternative bridging arrangement, and [Mn(bsalen)(MeOH)(OClO3)]. H2O (bsalen = 5-bromo derivative) highlights the versatility of the manganese centre in these systems where, unexpectedly, perchlorate is co-ordinated in place of a lattice water. A more subtle rearrangement of supramolecular structure is obtained in [Mn(nsalen)Cl(H2O)] where the usual combination of pi- or hydrogen-bonding interaction is modified by the corresponding ability of the 5-NO2 substituent.

  DOI：

  10.1039/dt9960002935
• 作为产物：
  描述：

  乙二胺 、 5-硝基水杨醛 在 乙醇 作用下， 生成 N,N'-bis(5-nitrosalicylidene)-1,2-diaminoethane
  参考文献：
  名称：

  Tsumaki et al., Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1943, vol. 64, p. 727,730

  摘要：

  DOI：

文献信息

• Experimental and theoretical structural determination, spectroscopy and electrochemistry of cobalt (III) Schiff base complexes: immobilization of complexes onto Montmorillonite-K10 nanoclay
  作者：Ali Hossein Kianfar、Sanaz Tavanapour、Kiamars Eskandari、Mohammad Hossein Azarian、Wan Ahmad Kamil Mahmood、Maryam Bagheri

  DOI：10.1007/s13738-017-1238-2

  日期：2018.2

  X = H, MeO, NO2, Br) complexes were successfully synthesized and characterized by different techniques such as FT-IR, UV–Vis, 1HNMR, 13CNMR and 31PNMR. The coordination geometry of the [Co(5-BrSalen)(PEt3)(H2O)]ClO4 complex was determined by X-ray crystallography. The complex has six-coordinated pseudo-octahedral geometry in which the O(1), O(2), N(1) and N(2) atoms of the Schiff base form the equatorial

  摘要[Co（5-XSalen）（PEt 3）（H 2 O）] ClO 4（其中Salen =双（水杨醛）1,2-乙二胺和X = H，MeO，NO 2，Br）配合物已成功合成并合成通过FT-IR，UV-Vis，1 HNMR，13 CNMR和31 PNMR等不同技术进行表征。[Co（5-BrSalen）（PEt 3）（H 2 O）] ClO 4的配位几何配合物通过X射线晶体学测定。该配合物具有六配位的伪八面体几何形状，其中席夫碱的O（1），O（2），N（1）和N（2）原子形成赤道面。循环伏安法研究了钴配合物的电化学性质，结果表明，当MeO
• New tetradentate Schiff bases, their oxovanadium(IV) complexes, and some complexes of bidentate Schiff bases with vanadium(III)
  作者：Nosheen Choudhary、David L. Hughes、Uwe Kleinkes、Leslie F. Larkworthy、G.Jeffery Leigh、Michael Maiwald、Celine J. Marmion、J.Roger Sanders、Gallenius W. Smith、Claas Sudbrake

  DOI：10.1016/s0277-5387(96)00436-6

  日期：1997.1

  Abstract New vanadyl(IV) complexes of tetradentate Schiff-base dianions containing one, two or three carbon atoms between the two iminato-nitrogen atoms are described. The compounds are either mononuclear or polymeric, as shown by the value of v(V=O), and depending upon the Schiff-base dianion. There is no evidence for electron delocalization along the polymeric chains. Some vanadium(III) complexes

  摘要描述了在两个亚氨基氮原子之间包含一个，两个或三个碳原子的四齿席夫碱双阴离子新的钒（IV）配合物。这些化合物是单核的或高分子的，如v（V = O）的值所示，具体取决于席夫碱的二价阴离子。没有证据表明电子会沿着聚合物链发生离域化。还分离了一些双齿席夫碱单阴离子钒（III）配合物。报道了[VO（2-OC6H4CHNH）2]的晶体结构和[V（Prhap）3]·甲苯[HPrhap = 2-HOC6H4C（Me）NCH2CH2Me]的结构的初步数据。
• Epoxidation of olefins with cationic (salen)manganese(III) complexes. The modulation of catalytic activity by substituents
  作者：K. Srinivasan、P. Michaud、Jay K. Kochi

  DOI：10.1021/ja00269a029

  日期：1986.4

  Augmentation d'activite avec des substituants attracteurs d'electrons (dichloro ou dinitro)

  增强 d'activite avec des substituants 吸引力 d'electrons (dichloro ou dinitro)
• Reactions of Manganese(III) Schiff Base Complexes with Superoxide Ion in Dimethyl Sulfoxide
  作者：Takayuki Matsushita、Toshiyuki Shono

  DOI：10.1246/bcsj.54.3743

  日期：1981.12

  The reactions of the chloromanganese(III) complexes of the Schiff bases derived from salicylaldehydes or β-diketones and diamines or monoamines with superoxide ion, O2−, in dimethyl sulfoxide were investigated. The complexes were found to react to give either the oxygenated Mn Schiff base complexes or the reduced Mn(II) Schiff base complexes. The difference in the reactivity toward O2− was correlated

  研究了衍生自水杨醛或 β-二酮和二胺或单胺的希夫碱的氯锰 (III) 配合物与超氧离子 O2- 在二甲基亚砜中的反应。发现这些配合物反应生成氧化的 Mn Schiff 碱配合物或还原的 Mn(II) Schiff 碱配合物。对 O2- 反应性的差异与极谱半波电位相关，对应于配合物的 Mn(III) 还原为 Mn(II)。一些含氧配合物被分离和表征。
• Synthesis, Crystal Structures and Catalytic Oxidation of Manganese(III) Complexes Derived from Salen-Type Schiff Base N,N’-Bis(5-nitrosalicylidene)ethane-1,2-diamine
  作者：Qing-Bin Li、Yong-Jun Han、Gan-Qing Zhao、Ling-Wei Xue

  DOI：10.17344/acsi.2017.3416

  日期：2017.6.15

  Schiff base manganese(III) complexes, [MnL(N3)(OH2)]·CH3OH (1) and [MnL(NCS)(OH2)] · H2O (2), where L is the dianionic form of N,N'-bis(5-nitrosalicylidene)ethane-1,2-diamine, have been prepared and characterized by elemental analysis, IR and UV-Vis spectroscopy and single crystal X-ray diffraction. The Mn atom in each complex is in an octahedral coordination. Molecules of the complexes are linked through

  两种单核席夫碱锰（III）配合物[MnL（N3）（OH2）]·CH3OH（1）和[MnL（NCS）（OH2）]·H2O（2），其中L是N，N的二价阴离子形式已制备了'-双（5-亚硝基水杨基）乙烷-1，2-二胺，并通过元素分析，IR和UV-Vis光谱以及单晶X射线衍射对其进行了表征。每个络合物中的Mn原子为八面体配位形式。配合物的分子通过分子间的氢键连接。已经研究了使用PhIO和NaOCl作为氧化剂的配合物对苯乙烯环氧化的催化性能。