4-chloro-N-(1-pyridin-2-ylethylideneamino)aniline;hydrochloride | 1164478-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-N-(1-pyridin-2-ylethylideneamino)aniline;hydrochloride
• CAS: 1164478-85-6
• 化学式: C₁₃H₁₂ClN₃*ClH
• 分子量: 282.172
• InChiKey: YCCXFPJUPRNBBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基吡啶 、 对氯苯肼盐酸盐 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-chloro-N-(1-pyridin-2-ylethylideneamino)aniline;hydrochloride
  参考文献：
  名称：

  Structural comparison of threeN-(4-halogenophenyl)-N′-[1-(2-pyridyl)ethylidene]hydrazine hydrochlorides

  摘要：

  2-{1-[(4-Chloroanilino)methylidene]ethyl}pyridinium chloride methanol solvate, C(13)H(13)ClN(3)(+)center dot Cl(-)center dot CH(3)OH, (I), crystallizes as discrete cations and anions, with one molecule of methanol as solvent in the asymmetric unit. The N-C-C-N torsion angle in the cation indicates a cis conformation. The cations are located parallel to the ((2) over bar 02) plane and are connected through hydrogen bonds by a methanol solvent molecule and a chloride anion, forming zigzag chains in the direction of the b axis. The crystal structure of 2-{1-[(4-fluoroanilino)methylidene]ethyl}pyridinium chloride, C(13)H(13)FN(3)(+)center dot Cl(-), (II), contains just one anion and one cation in the asymmetric unit but no solvent. In contrast with (I), the N-C-C-N torsion angle in the cation corresponds with a trans conformation. The cations are located parallel to the (100) plane and are connected by hydrogen bonds to the chloride anions, forming zigzag chains in the direction of the b axis. In addition, the crystal packing is stabilized by weak pi-pi interactions between the pyridinium and benzene rings. The crystal of (II) is a nonmerohedral monoclinic twin which emulates an orthorhombic diffraction pattern. Twinning occurs via a twofold rotation about the c axis and the fractional contribution of the minor twin component refined to 0.324 (3). 2-{1-[(4-Fluoroanilino)methylidene]ethyl}pyridinium chloride methanol disolvate, C(13)H(13)FN(3)(+)center dot Cl(-)center dot 2CH(3)OH, (III), is a pseudopolymorph of (II). It crystallizes with two anions, two cations and four molecules of methanol in the asymmetric unit. Two symmetry-equivalent cations are connected by hydrogen bonds to a chloride anion and a methanol solvent molecule, forming a centrosymmetric dimer. A further methanol molecule is hydrogen bonded to each chloride anion. These aggregates are connected by C-H center dot center dot center dot O contacts to form infinite chains. It is remarkable that the geometric structures of two compounds having two different formula units in their asymmetric units are essentially the same.

  DOI：

  10.1107/s0108270110019827

文献信息

• Structural comparison of three<i>N</i>-(4-halogenophenyl)-<i>N</i>′-[1-(2-pyridyl)ethylidene]hydrazine hydrochlorides
  作者：Julia Heilmann-Brohl、Matthias Wagner、Hans-Wolfram Lerner、Michael Bolte

  DOI：10.1107/s0108270110019827

  日期：2010.7.15

  2-1-[(4-Chloroanilino)methylidene]ethyl}pyridinium chloride methanol solvate, C(13)H(13)ClN(3)(+)center dot Cl(-)center dot CH(3)OH, (I), crystallizes as discrete cations and anions, with one molecule of methanol as solvent in the asymmetric unit. The N-C-C-N torsion angle in the cation indicates a cis conformation. The cations are located parallel to the ((2) over bar 02) plane and are connected through hydrogen bonds by a methanol solvent molecule and a chloride anion, forming zigzag chains in the direction of the b axis. The crystal structure of 2-1-[(4-fluoroanilino)methylidene]ethyl}pyridinium chloride, C(13)H(13)FN(3)(+)center dot Cl(-), (II), contains just one anion and one cation in the asymmetric unit but no solvent. In contrast with (I), the N-C-C-N torsion angle in the cation corresponds with a trans conformation. The cations are located parallel to the (100) plane and are connected by hydrogen bonds to the chloride anions, forming zigzag chains in the direction of the b axis. In addition, the crystal packing is stabilized by weak pi-pi interactions between the pyridinium and benzene rings. The crystal of (II) is a nonmerohedral monoclinic twin which emulates an orthorhombic diffraction pattern. Twinning occurs via a twofold rotation about the c axis and the fractional contribution of the minor twin component refined to 0.324 (3). 2-1-[(4-Fluoroanilino)methylidene]ethyl}pyridinium chloride methanol disolvate, C(13)H(13)FN(3)(+)center dot Cl(-)center dot 2CH(3)OH, (III), is a pseudopolymorph of (II). It crystallizes with two anions, two cations and four molecules of methanol in the asymmetric unit. Two symmetry-equivalent cations are connected by hydrogen bonds to a chloride anion and a methanol solvent molecule, forming a centrosymmetric dimer. A further methanol molecule is hydrogen bonded to each chloride anion. These aggregates are connected by C-H center dot center dot center dot O contacts to form infinite chains. It is remarkable that the geometric structures of two compounds having two different formula units in their asymmetric units are essentially the same.