N-methyldi(1H-2-imidazolyl)methanamine | 64269-83-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyldi(1H-2-imidazolyl)methanamine
• 英文别名: bis(imidazol-2-yl)methylaminomethane；bis(imidazol-2-yl)methyl amino methane；BIMAM；[bis-(1H-imidazol-2-yl)-methyl]-methyl-amine；Bismethylaminomethan；1,1-bis(1H-imidazol-2-yl)-N-methylmethanamine
• CAS: 64269-83-6
• 化学式: C₈H₁₁N₅
• 分子量: 177.209
• InChiKey: LFUHSYLBTATEIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyldi(1H-2-imidazolyl)methanamine 、 copper(II) choride dihydrate 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Copper(II) Coordination Compounds with Bis(imidazol-2-yl)methylamine and Bis(imidazol-2-yl)methylaminomethane in Relation to Bis(imidazol-2-yl)methylamine-Modified Poly(glycidyl methacrylate) Polymers and Other Bis(imidazol-2-yl)-Containing Ligands

  摘要：

  The synthesis, spectroscopy, and structure of three Cu(II) coordination compounds of the ligands bis(imidazol-2-yl)methylaminomethane (bimam) and bis(imidazol-2-yl)methylamine (bima) are described. The ligands bimam and bima both coordinate to Cu(II) ions in a didentate fashion. In all three complexes the copper(II) ions are coordinated in a distorted octahedral geometry. In [Cu(Hbimam)Cl-3](2)(H2O)(2) and [Cu(Hbima)Cl-3](2)(H2O)(2) each Cu(lI) ion is coordinated by two imidazole nitrogens and four chloride anions. The two mononuclear units are connected by two asymmetric chloride bridges. In [Cu(Hbimam)(2)Cl-2]Cl-2(H2O)(2) the Cu(II) ion is coordinated by four imidazole nitrogens and two chloride anions. In the present complexes the amine nitrogen donor of the ligand is hydronated and not coordinated to the Cu(II) ion. [(De)hydronated is the recommended IUPAC expression to indicate loss/addition of H+.] In all three complexes strong hydrogen bonding is observed between the amine nitrogen donor(s) and the axial coordinated chloride(s). X-ray crystallographic parameters for the copper complexes are as follows: [Cu(Hbimam)Cl-3](2)(H2O)(2), monoclinic, space group P2(1)/c, Z = 4, a = 12.6259(8) Angstrom, b = 8.3452(4) Angstrom, c = 15.9280(8) Angstrom, beta = 124.458(5)degrees, V = 1383.80(15) Angstrom(3), R = 0.037, R(w) = 0.047 for 2792 reflections with I > 2.5 sigma(I); Cu-N 2.0271(18) and 1.992(2) Angstrom, Cu-Cl 2.2705(8), 2.2854(8) 2.9266(11), and 3.2212(12) Angstrom. [Cu(Hbimam)(2)Cl-2]Cl-2(H2O)(2), monoclinic, space group P2(1)/c, Z = 4, a = 7.6507(5) Angstrom, b = 21.4241(13) Angstrom, c = 14.8152(12) Angstrom, beta 93.285(6)degrees, V = 2424.4(3) Angstrom(3), R = 0.0289 for 4781 reflections with I > 2 sigma(I), wR2 = 0.0716 for 5534 reflections; Cu-N 2.0201(15), 1.9970(15), 2.0082(15), and 2.0102(15) Angstrom; Cu-Cl2.9019(5) and 2.9064(5) Angstrom. [Cu(Hbima)Cl-3](2)(H2O)(2), monoclinic space group P2(1)/c, Z = 4, a = 12.549(2) Angstrom, b = 8.345(2) Angstrom, c = 16.630(4) Angstrom, beta 126.22(2)degrees, V = 1405.0(6) Angstrom(3), R = 0.077 for 1774 reflections with I > 2 sigma(I), wR2 = 0.190 for 3208 reflections; Cu-N 1.997(6) and 2.018(6) Angstrom; Cu-Cl2.284(2), 2.286(2), 2.970(3), and 2.9843(3) Angstrom. The ligand bimam was also immobilized onto a solid support, poly(glycidyl methacrylate-co-trimethylolpropane trimethacrylate) (p(GMT)), yielding a very Cu(II)-selective chelating ion-exchange resin pGMT-bimam with high uptake capacity. The resin retains its high uptake capacity for Cu(II) even in the presence of 1,2-diaminoethane, 1,3-diaminopropane and 1,4-diaminobutane as competing ligands in solution. When tartrate is used as a competitor, even a positive effect on the Cu(II) uptake is observed. For Na(2)H(2)edta as competitor in solution, both a pH effect and a concentration effect were noticed; i.e., with increasing pH and increasing molar ratios (Na(2)H(2)edta: Cu(II)) the Cu(II) uptake of the ion exchanger decreases rapidly. Comparative spectroscopic studies of the coordination compounds with bimam and bima in their relationship to chelation of Cu(lI) ions on the ion-exchange resin pGMT-bimam, have shown that on the resin only 1:2 (Cu(II):bimam) complexes are formed.

  DOI：

  10.1021/ic9513705
• 作为产物：
  描述：

  2,2'-(nitromethylene)bis(1H-imidazole) 、 甲胺 以80%的产率得到
  参考文献：
  名称：

  JOSEPH M.; LEIGH T.; SWAIN M. L., SYNTHESIS , 1977, NO 7, 459-461

  摘要：

  DOI：

文献信息

• A novel dinuclear manganese(II) compound incorporating two bis(imidazolyl) based ligands with single μ2-η1:η1-carboxylato bridges. Molecular and crystal structure and magnetic properties of [Mn2Cl(BIP)(HBIMAM)(H2O)5]Cl3·4H2O (BIP=3,3-di(2-1H-2-imidazolyl)propanoate; BIMAM=N-methyldi(1H-2-imidazolyl)methanamine)
  作者：Emilio Escrivà、Luis Lezama、Lucía Soto、Amparo Sancho、José-Vicente Folgado、Carmen Ramírez de Arellano

  DOI：10.1016/j.poly.2013.11.008

  日期：2014.1

  characterization of [Mn 2 Cl(BIP) (HBIMAM)(H 2 O) 5 ]Cl 3 ·4H 2 O a novel dinuclear manganese(II) incorporating two related bis(imidazolyl)-based ligands, BIP (3,3-di(2-1 H -2-imidazolyl)propanoate) and BIMAM ( N -methyldi(1 H -2-imidazolyl)methanamine). The metal atoms in the dinuclear entity are bridged by a μ 2 -η 1 :η 1 carboxylate group (from the propionate arm of the BIP ligand) acting in an anti – anti coordination

  摘要本文报道了一种新型的[Mn 2 Cl（BIP）（HBIMAM）（H 2 O）5] Cl 3·4H 2 O的合成，X射线结构和磁特性。基于咪唑基）的配体，BIP（3,3-二（2-1 H -2-咪唑基）丙酸酯）和BIMAM（N-甲基二（1 H -2-咪唑基）甲胺）。双核实体中的金属原子被μ2-η1：η1羧酸根基团（来自BIP配体的丙酸酯臂）桥接，以抗-反配位桥接方式起作用，分子内Mn⋯Mn距离为6.47答：Mn（II）离子周围的配位对于MnClN 2 O 3和MnN 2 O 4发色团均显示扭曲的八面体几何形状。在相邻的双核单元的咪唑环之间，存在明显的芳族-芳族相互作用。这些相互作用的传播产生了π堆积的双核单元的链，大致沿[1 0 0]方向延伸。在2–300 K范围内的磁化率测量结果显示弱的反铁磁交换相互作用，可以通过各向同性S 1 = S 2 = 5/2自旋耦合二聚体模型H ˆ =-2 J（S
• Structure, spectroscopic and magnetic properties of a novel 1-D coordination copper(II) polymer containing BIMAM ligand [BIMAM=bis(imidazol-2-yl)methylaminomethane] and μ-1,3 squarato bridges
  作者：Lucía Soto、Nailette Ruiz、Hugo Núñez、Juan Server-Carrió、Emilio Escrivà、Amparo Sancho、Julia García-Lozano

  DOI：10.1016/j.ica.2006.03.039

  日期：2006.7

  coordination polyhedron about the copper(II) ion is distorted square pyramidal. The EPR spectrum is indicative of a d z 2 -y 2 d z 2 - y 2 ground state for the Cu(II) ions with significant contribution of d z 2 d z 2 . Magnetic susceptibility measurements in the range 1.8–200 K show weak antiferromagnetic exchange interactions (2 J = −3.5(1) cm −1 ). The observed magnetic behaviour is discussed in terms

  本文报道了[Cu（HBIMAM）Cl（C 4 O 4）] n·（H 2 O）n [BIMAM =双（咪唑-2-基）甲基氨基甲烷]的合成及完整表征（结构，光谱和磁性）。 。该化合物由[cCl（HBIMAM）] +由μ-O1，O 3 -bis（单齿）方酸根阴离子桥连的单元组成，沿c轴延伸的无限链组成。非共价相互作用（H键和π–π）驱动无限的三维阵列的建立。关于铜（II）离子的配位多面体是扭曲的方形锥体。EPR谱表示Cu（II）离子的adz 2 -y 2 dz 2-y 2基态，对dz 2 dz 2的贡献很大。在1.8-200 K范围内的磁化率测量结果显示弱的反铁磁交换相互作用（2 J = -3.5（1）cm -1）。
• A novel coordination polymer with an unusual [3×2] oblique copper(II) grid: [Cu2(HBIMAM)2(C4O4)3(H2O)2]n·2nH2O [BIMAM=bis(imidazol-2-yl)methylaminomethane]. X-ray structure and magnetic characterization
  作者：Emilio Escrivá、Lucía Soto、Juan Server-Carrió、Carlos J. Gómez-García、Guillermo Mínguez Espallargas、Nailette Ruiz、Amparo Sancho、Julia García-Lozano、Carmen Ramírez de Arellano

  DOI：10.1016/j.poly.2013.03.016

  日期：2013.6

  characterization of [Cu2(HBIMAM)2(C4O4)3(H2O)2]n·2nH2O [BIMAM = bis(imidazol-2-yl)methylamino methane]. This compound is made of infinite chains – running along the [1 1 0] direction – with copper ions bridged by μ1,3-squarato ligands. Furthermore, these chains are further cross-linked through additional squarate anions (with the same μ1,3-bis(monodentate) bridging mode) to generate two-dimensional sheets parallel

  本文报道了[Cu 2（HBIMAM）2（C 4 O 4）3（H 2 O）2 ] n ·2 n H 2 O [BIMAM = bis（imidazol-2） -基）甲氨基甲烷]。该化合物是由无限链-沿[1 1 0]方向运行-与铜离子桥接由μ 1,3 -squarato配体。此外，这些链是进一步交联通过附加方酸二阴离子（具有相同的μ 1,3-双（单齿）桥接模式），以产生平行于二维薄片AB飞机。链中每两个铜原子有链间链接，形成不寻常的（3×2）斜铜（II）网格。在2–300 K范围内的磁化率测量结果显示弱的反铁磁交换相互作用。对结构的详细分析表明，用于重现磁性能的更合适的模型是包含 链间相互作用（j '）的常规S = 1/2反铁磁链模型。最后，所观察到的磁性行为（Ĵ链 = -0.97（1）厘米-1和Ĵ '= -0.03（1）厘米-1）与在相关的六配位铜观察到（II）的化合物相比，含有μ 1,3 -方形桥。
• Copper(II) Coordination Compounds with Bis(imidazol-2-yl)methylamine and Bis(imidazol-2-yl)methylaminomethane in Relation to Bis(imidazol-2-yl)methylamine-Modified Poly(glycidyl methacrylate) Polymers and Other Bis(imidazol-2-yl)-Containing Ligands
  作者：G. J. Anthony A. Koolhaas、Petronella M. van Berkel、Saskia C. van der Slot、Guillermo Mendoza-Diaz、Willem L. Driessen、Jan Reedijk、Huub Kooijman、Nora Veldman、Anthony L. Spek

  DOI：10.1021/ic9513705

  日期：1996.1.1

  The synthesis, spectroscopy, and structure of three Cu(II) coordination compounds of the ligands bis(imidazol-2-yl)methylaminomethane (bimam) and bis(imidazol-2-yl)methylamine (bima) are described. The ligands bimam and bima both coordinate to Cu(II) ions in a didentate fashion. In all three complexes the copper(II) ions are coordinated in a distorted octahedral geometry. In [Cu(Hbimam)Cl-3](2)(H2O)(2) and [Cu(Hbima)Cl-3](2)(H2O)(2) each Cu(lI) ion is coordinated by two imidazole nitrogens and four chloride anions. The two mononuclear units are connected by two asymmetric chloride bridges. In [Cu(Hbimam)(2)Cl-2]Cl-2(H2O)(2) the Cu(II) ion is coordinated by four imidazole nitrogens and two chloride anions. In the present complexes the amine nitrogen donor of the ligand is hydronated and not coordinated to the Cu(II) ion. [(De)hydronated is the recommended IUPAC expression to indicate loss/addition of H+.] In all three complexes strong hydrogen bonding is observed between the amine nitrogen donor(s) and the axial coordinated chloride(s). X-ray crystallographic parameters for the copper complexes are as follows: [Cu(Hbimam)Cl-3](2)(H2O)(2), monoclinic, space group P2(1)/c, Z = 4, a = 12.6259(8) Angstrom, b = 8.3452(4) Angstrom, c = 15.9280(8) Angstrom, beta = 124.458(5)degrees, V = 1383.80(15) Angstrom(3), R = 0.037, R(w) = 0.047 for 2792 reflections with I > 2.5 sigma(I); Cu-N 2.0271(18) and 1.992(2) Angstrom, Cu-Cl 2.2705(8), 2.2854(8) 2.9266(11), and 3.2212(12) Angstrom. [Cu(Hbimam)(2)Cl-2]Cl-2(H2O)(2), monoclinic, space group P2(1)/c, Z = 4, a = 7.6507(5) Angstrom, b = 21.4241(13) Angstrom, c = 14.8152(12) Angstrom, beta 93.285(6)degrees, V = 2424.4(3) Angstrom(3), R = 0.0289 for 4781 reflections with I > 2 sigma(I), wR2 = 0.0716 for 5534 reflections; Cu-N 2.0201(15), 1.9970(15), 2.0082(15), and 2.0102(15) Angstrom; Cu-Cl2.9019(5) and 2.9064(5) Angstrom. [Cu(Hbima)Cl-3](2)(H2O)(2), monoclinic space group P2(1)/c, Z = 4, a = 12.549(2) Angstrom, b = 8.345(2) Angstrom, c = 16.630(4) Angstrom, beta 126.22(2)degrees, V = 1405.0(6) Angstrom(3), R = 0.077 for 1774 reflections with I > 2 sigma(I), wR2 = 0.190 for 3208 reflections; Cu-N 1.997(6) and 2.018(6) Angstrom; Cu-Cl2.284(2), 2.286(2), 2.970(3), and 2.9843(3) Angstrom. The ligand bimam was also immobilized onto a solid support, poly(glycidyl methacrylate-co-trimethylolpropane trimethacrylate) (p(GMT)), yielding a very Cu(II)-selective chelating ion-exchange resin pGMT-bimam with high uptake capacity. The resin retains its high uptake capacity for Cu(II) even in the presence of 1,2-diaminoethane, 1,3-diaminopropane and 1,4-diaminobutane as competing ligands in solution. When tartrate is used as a competitor, even a positive effect on the Cu(II) uptake is observed. For Na(2)H(2)edta as competitor in solution, both a pH effect and a concentration effect were noticed; i.e., with increasing pH and increasing molar ratios (Na(2)H(2)edta: Cu(II)) the Cu(II) uptake of the ion exchanger decreases rapidly. Comparative spectroscopic studies of the coordination compounds with bimam and bima in their relationship to chelation of Cu(lI) ions on the ion-exchange resin pGMT-bimam, have shown that on the resin only 1:2 (Cu(II):bimam) complexes are formed.
• JOSEPH M.; LEIGH T.; SWAIN M. L., SYNTHESIS <SYNT-BF>, 1977, NO 7, 459-461
  作者：JOSEPH M.、 LEIGH T.、 SWAIN M. L.

  DOI：——

  日期：——