2,7-dimethyl-4,9-diazapyrene | 220934-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2,7-dimethyl-4,9-diazapyrene
• 英文别名: 6,13-Dimethyl-2,9-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaene
• CAS: 220934-96-3
• 化学式: C₁₆H₁₂N₂
• 分子量: 232.285
• InChiKey: PMQBLNPVZYTRIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 2,7-dimethyl-4,9-diazapyrene 以 various solvent(s) 为溶剂， 反应 0.5h， 以66%的产率得到2,4,7,9-tetramethyl-4,9-diazapyrene-4,9-diium triflate
  参考文献：
  名称：

  Piantanida, Ivo; Tomisic, Vladislav; Zinic, Mladen, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 2, p. 375 - 383

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2'-diformamido-4,4'-dimethylbiphenyl 在 三氯化铝 、 sodium chloride 作用下， 反应 2.0h， 以25%的产率得到2,7-dimethyl-4,9-diazapyrene
  参考文献：
  名称：

  Piantanida, Ivo; Tomisic, Vladislav; Zinic, Mladen, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 2, p. 375 - 383

  摘要：

  DOI：

文献信息

• Crystal and molecular structures of diazapyrenes and a study of π\cdotsπ interactions
  作者：Rudolf Kiralj、Biserka Kojić-Prodić、Ivo Piantanida、Mladen Žinić

  DOI：10.1107/s0108768198006557

  日期：1999.2.1

  Two diazapyrenes, 5,10-dimethyl-4,9-diazapyrene (1) and novel 2,7-dimethyl-4,9-diazapyrene (2) have been synthesized. Their crystal structures are reported here and are the first representatives of diazapyrenes. Crystal data: (1) monoclinic, P2₁/c, a = 4.0246 (5), b = 15.5147 (5), c = 9.1453 (9) Å, β = 101.23 (1)°, V = 560.1 (1) ų, Z = 2, R = 0.043; (2) monoclinic, C2/m, a = 12.4968 (3), b = 11.4751 (4), c = 3.9615 (5) Å, β = 96.80 (1)°, V = 564.09 (5) ų, Z = 2, R = 0.0405. The experimental bond lengths are compared with those calculated by molecular mechanics (MM3), semi-empirical methods (MOPAC6.0-PM3, AM1, MNDO) and values predicted by valence-bond and variable-electronegativity self-consistent field (VESCF) methods. π\cdotsπ interactions in (1), (2) and seventeen other pyrene and pyrene-like molecules selected from the Cambridge Structural Database [Allen & Kennard (1993). Chem. Des. Autom. News, 8, 131–137] have been studied. The following quantitative parameters of π\cdotsπ interactions have been calculated: the shortest crystallographic axis, the offset parameter, the interplanar angle, the interactive volume and the overlapping surfaces. They are used for the classification of crystal-packing motifs; a high predominance of β and a few cases of γ and sandwich-herringbone types are observed. In addition, electronegativity, the sum of partial atomic charges of the ring non-H atoms and the number of aromatic skeleton electrons are used as parameters for classification. MOPAC-PM3 was used to calculate the partial atomic charges in (1), (2) and pyrene analogues. Correlations between geometrical and electronic structure parameters reveal an analogy between the β-type structures and the crystal structure of graphite.

  我们合成了两种二氮杂环戊烯，即 5,10-二甲基-4,9-二氮杂环戊烯（1）和新型 2,7-二甲基-4,9-二氮杂环戊烯（2）。本文报告了它们的晶体结构，它们是二氮杂并芘的首批代表。晶体数据：(1) 单斜，P21/c，a = 4.0246 (5)，b = 15.5147 (5)，c = 9.1453 (9) Å，β = 101.23 (1)°，V = 560.1 (1) Å3，Z = 2，R = 0.043；（2）单斜，C2/m，a = 12.4968 (3)，b = 11.4751 (4)，c = 3.9615 (5)埃，β = 96.80 (1)°，V = 564.09 (5) Å3，Z = 2，R = 0.0405。实验键长与分子力学 (MM3)、半经验方法 (MOPAC6.0-PM3、AM1、MNDO) 计算的键长以及价键和变电负性自洽场 (VESCF) 方法预测的键长进行了比较。从剑桥结构数据库 [Allen &AMp; Kennard (1993). Chem. Des. Autom. News, 8, 131-137] 中选取了 (1)、(2) 和其他十七种芘和类芘分子中的πcdotsπ 相互作用进行了研究。计算出了π/cdotsπ相互作用的以下定量参数：最短晶轴、偏移参数、平面间角度、相互作用体积和重叠面。它们被用于晶体堆积图案的分类；观察到的晶体堆积图案主要是 β 型，少数是 γ 型和三明治-人字形型。此外，电负性、环上非 H 原子的部分原子电荷之和以及芳香骨架电子数也被用作分类参数。MOPAC-PM3 用于计算 (1)、(2) 和芘类似物的部分原子电荷。几何和电子结构参数之间的相关性揭示了 β 型结构与石墨晶体结构之间的相似性。