(2-methylimidazol-4-yl)methylideneamino-2-ethylpyridine | 945663-02-5

• 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: (2-methylimidazol-4-yl)methylideneamino-2-ethylpyridine
• 英文别名: 1-(2-methyl-1H-imidazol-5-yl)-N-(2-pyridin-2-ylethyl)methanimine
• CAS: 945663-02-5
• 化学式: C₁₂H₁₄N₄
• 分子量: 214.27
• InChiKey: LBCSCYIVZIWEDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-methylimidazol-4-yl)methylideneamino-2-ethylpyridine 、 iron(II) perchlorate hexahydrate 以 乙醇 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Synthesis, structures, and magnetic properties of iron(II) complexes, [FeII(HLMe)2](ClO4)2 and its ethanol adduct [FeII(HLMe)2](ClO4)2·EtOH (HLMe=2-methylimidazol-4-yl-methylideneamino-2-ethylpyridine): Their structural distortion and spin states

  摘要：

  Two new iron(II) complexes, [Fe-II(HLMe)(2)](ClO4)(2) (1) and its ethanol adduct [Fe-II(HLMe)(2)](ClO4)(2)center dot EtOH (2) were synthesized by selective crystallization in methanol and ethanol, respectively, where HLMe is a tridentate N-3 ligand, 2-methylimidazol-4-yl-methylideneamino-2-ethylpyridine, and their structures and magnetic properties were investigated. Each compound contains the same octahedrally N-6 coordinated complex-cation [Fe-II(HLMe)(2)](2+) and two ClO4- ions. The non-solvated compound 1 is the HS (S = 2) complex without spin transition over the 5-300 K temperature range, and has the homochiral 1D helical-chain structure constructed of the intermolecular NH center dot center dot center dot O- hydrogen bonds between ClO4- ions and neighboring imidazole NH groups of the [Fe-II(HLMe)(2)](2+) cations. The ethanol adduct 2 shows a gradual one-step spin transition between the HS (S = 2) and LS (S = 0) states, and has two crystallographically independent iron(II) sites with two NH(imidazole)center dot center dot OH(EtoH)center dot center dot center dot O(ClO4-) hydrogen bonds of Fe(1) site and two NH(imidazole)center dot center dot center dot O(ClO4-) hydrogen bonds of Fe(2) site. There are no further intermolecular interactions to produce an extended structure in a crystal lattice of 2. The presence or absence of thermal spin transition is related to the structural distortion of each HS molecule of these perchlorate salts associated with their surroundings of intermolecular hydrogen bonds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.09.010
• 作为产物：
  描述：

  2-(2-氨乙基)吡啶 、 2-甲基咪唑-4-甲醛 以 甲醇 为溶剂， 反应 0.25h， 生成 (2-methylimidazol-4-yl)methylideneamino-2-ethylpyridine
  参考文献：
  名称：

  (2-甲基咪唑-4-基)亚甲基氨基-2-乙基吡啶的自旋交叉铁(II)配合物：2:1 [Fe(HLMe)2](PF6)2和3:1 [Fe(HLMe)3](PF6) 2

  摘要：

  (2-甲基咪唑-4-基)亚甲基氨基-2-乙基吡啶 (HLMe) 作为 FeII 离子的双齿或三齿配体，产生 2:1 复合物 [Fe(HLMe)2](PF6)2 (1) 和3:1 复杂 [F...

  DOI：

  10.1246/cl.2007.778

文献信息

• One-Dimensional Spin-Crossover Iron(II) Complexes Bridged by Intermolecular Imidazole−Pyridine NH···N Hydrogen Bonds, [Fe(HL^Me)₃]X₂ (HL^Me = (2-Methylimidazol-4-yl-methylideneamino-2-ethylpyridine; X = PF₆, ClO₄, BF₄)
  作者：Koshiro Nishi、Shinobu Arata、Naohide Matsumoto、Seiichiro Iijima、Yukinari Sunatsuki、Hiroyuki Ishida、Masaaki Kojima

  DOI：10.1021/ic9017344

  日期：2010.2.15

  2-Methylimidazol-4-yl-methylideneamino-2-ethylpyddine (abbreviated as HLMe) is the 1:1 condensation product of 2-methyl-4-formylimidazole and 2-aminoethylpyridine and functions as a bidentate ligand to the iron(II) ion to produce the 3:1 complexes together with anions, [Fe(HLMe)(3)]X-2 (X = PF6 (1), ClO4 (2), BF4 (3)). The magnetic susceptibilities, differential scanning calorimetric measurements, and Mossbauer spectral measurements demonstrated that complexes 1, 2, and 3 showed a steep one-step spin crossover (SCO) between the high-spin (HS, S=2) and low-spin (LS, S = 0) states with small thermal hysteresis. Three complexes have an isomorphous structure and are crystallized in the same monoclinic space group, C2/c, both in the HS and LS states. The iron(II) ion has the octahedral coordination geometry of a facial isomer with N-6 donor atoms of three bidentate ligands, in which an imidazole and an imine nitrogen atom per ligand participate in the formation of the coordination bond, but the pyridine nitrogen is free from coordination. The complex cation fac-[Fe(HLMe)(3)](2+) is a chiral species with a Delta or Lambda isomer, and the adjacent Delta and Lambda isomers are linked alternately by an intermolecular imidazole-pyridine NH center dot center dot center dot N hydrogen bond to produce an achiral 1D chain. The two remaining imidazole moieties per complex are hydrogen-bonded to the anions that occupy the space among the chains. The SCO profile becomes steeper with the decrease of the anion size (73.0 angstrom(3) for PF6-, 54.4 angstrom(3) for ClO4-, and 53.4 angstrom(3) for BF4-). The SCO transition temperature T-1/2 of the PF6 (1), ClO4 (2), and BF4 (3) salts estimated from the magnetic susceptibility measurements are (T-down arrow = 151.8 K, T-up arrow = 155.3 K), (T-down arrow = 184.5 K, T-up arrow = 186.0 K), and (T-down arrow = 146.4 K, T-up arrow = 148.2 K), respectively, indicating that the T-1/2 value is not in accord with the anion size.