4,6-dinitro-N,N'-di-n-undecylbenzene-1,3-diamine | 217079-87-3

• 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: 4,6-dinitro-N,N'-di-n-undecylbenzene-1,3-diamine
• 英文别名: 4,6-Dinitro-n,n'-di-n-undecylbenzene-1,3-diamine；4,6-dinitro-1-N,3-N-di(undecyl)benzene-1,3-diamine
• CAS: 217079-87-3
• 化学式: C₂₈H₅₀N₄O₄
• 分子量: 506.729
• InChiKey: CGIAPWHQKGYXSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  正十一胺 、 1,5-二氟-2,4-二硝基苯 在 potassium carbonate 作用下， 以 异丁酰胺 、 甲苯 为溶剂， 以78%的产率得到4,6-dinitro-N,N'-di-n-undecylbenzene-1,3-diamine
  参考文献：
  名称：

  4,6-Dinitro-N,N′-di-n-octylbenzene-1,3-diamine, 4,6-dinitro-N,N′-di-n-undecylbenzene-1,3-diamine andN,N′-bis(2,4-dinitrophenyl)octane-1,8-diamine

  摘要：

  4,6-Dinitro-N,N'-di-n-octylbenzene-1,3-diamine, C22H38N4O4, (I), 4,6-dinitro-N, N'-di-n-undecylbenzene-1,3-diamine, C28H50N4O4, (II), and N, N'-bis(2,4-dinitrophenyl)octane-1,8-diamine, C20H24N6O8, (III), are the first synthetic meta-dinitroarenes functionalized with long-chain aliphatic amine groups to be structurally characterized. The intra-and intermolecular interactions in these model compounds provide information that can be used to help understand the physical properties of corresponding polymers with similar functionalities. Compounds (I) and (II) possess near-mirror symmetry, with the octyl and undecyl chains adopting fully extended anti conformations in the same direction with respect to the ring. Compound (III) rests on a center of inversion that occupies the mid-point of the central C-C bond of the octyl chain. The middle six C atoms of the chain form an anti arrangement, while the remaining two C atoms take hard turns almost perpendicular to the rest of the chain. All three molecules display intramolecular N-H center dot center dot center dot O hydrogen bonds between the amine and nitro groups, with the same NH group forming a bifurcated intermolecular hydrogen bond to the nitro O atom of an adjacent molecule. In each case, these interactions link the molecules into one-dimensional molecular chains. In (I) and (II), these chains pack so that the pendant alkyl groups are interleaved parallel to one another, maximizing non-bonded C-H contacts. In (III), the alkyl groups are more isolated within the molecular chains and the primary non-bonded contacts between the chains appear to involve the nitro groups not involved in the hydrogen bonding.

  DOI：

  10.1107/s0108270109001619

文献信息

• 4,6-Dinitro-<i>N</i>,<i>N</i>′-di-<i>n</i>-octylbenzene-1,3-diamine, 4,6-dinitro-<i>N</i>,<i>N</i>′-di-<i>n</i>-undecylbenzene-1,3-diamine and<i>N</i>,<i>N</i>′-bis(2,4-dinitrophenyl)octane-1,8-diamine
  作者：Gary Teng、Christopher P. Walczak、Philip J. Squattrito、Dillip K. Mohanty、William Scharer、Mark R. Giolando、Kristin Kirschbaum

  DOI：10.1107/s0108270109001619

  日期：2009.2.15

  4,6-Dinitro-N,N'-di-n-octylbenzene-1,3-diamine, C22H38N4O4, (I), 4,6-dinitro-N, N'-di-n-undecylbenzene-1,3-diamine, C28H50N4O4, (II), and N, N'-bis(2,4-dinitrophenyl)octane-1,8-diamine, C20H24N6O8, (III), are the first synthetic meta-dinitroarenes functionalized with long-chain aliphatic amine groups to be structurally characterized. The intra-and intermolecular interactions in these model compounds provide information that can be used to help understand the physical properties of corresponding polymers with similar functionalities. Compounds (I) and (II) possess near-mirror symmetry, with the octyl and undecyl chains adopting fully extended anti conformations in the same direction with respect to the ring. Compound (III) rests on a center of inversion that occupies the mid-point of the central C-C bond of the octyl chain. The middle six C atoms of the chain form an anti arrangement, while the remaining two C atoms take hard turns almost perpendicular to the rest of the chain. All three molecules display intramolecular N-H center dot center dot center dot O hydrogen bonds between the amine and nitro groups, with the same NH group forming a bifurcated intermolecular hydrogen bond to the nitro O atom of an adjacent molecule. In each case, these interactions link the molecules into one-dimensional molecular chains. In (I) and (II), these chains pack so that the pendant alkyl groups are interleaved parallel to one another, maximizing non-bonded C-H contacts. In (III), the alkyl groups are more isolated within the molecular chains and the primary non-bonded contacts between the chains appear to involve the nitro groups not involved in the hydrogen bonding.