3,5-Bis(2-pyridylethynyl)-4-chloronitrobenzene

• 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: 3,5-Bis(2-pyridylethynyl)-4-chloronitrobenzene
• 英文别名: 2-[2-[2-Chloro-5-nitro-3-(2-pyridin-2-ylethynyl)phenyl]ethynyl]pyridine
• 化学式: C₂₀H₁₀ClN₃O₂
• 分子量: 359.771
• InChiKey: CSJHVPYPHHMEKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙炔基吡啶 、 3,5-Diiodo-4-chloronitrobenzene 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 20.0h， 以62%的产率得到3,5-Bis(2-pyridylethynyl)-4-chloronitrobenzene
  参考文献：
  名称：

  Molecular Association Mediated by Nitrogen-Chlorine Donor-Acceptor Interactions

  摘要：

  3,5-Bis(2-pyridylethynyl)-4-chloronitrobenzene (5) and 3,5-bis[[3-(4-(tert-butylbenzyl)oxy)-2-pyridyl]- ethynyl]-4-chloronitrobenzene (13) were synthesized as potential tridentate ligands, via nitrogen-chlorine donor-acceptor interactions, of 2,6-dichloropyridine and related compounds. Compound 5 was also synthesized in N-15-labeled form, and its association with 2,6-dichloropyridine, 2,6-dibromopyridine, 2,4,6-trichloropyrimidine, and 1,3-dichlorobenzene was examined by means of N-15 NMR titration experiments. The first three compounds were weakly associated with 5 (K-assoc = 0.2-0.3 M(-1)) in toluene solution and induced significant upfield shifts in its N-15 NMR resonances, but 1,3-dichlorobenzene, which cannot fit satisfactorily into the proposed ''cleft'' of compound 5, had little effect. The X-ray structure of 5 and the proposed structures of its complexes are discussed.

  DOI：

  10.1021/jo00127a025

文献信息

• Molecular Association Mediated by Nitrogen-Chlorine Donor-Acceptor Interactions
  作者：Kui Xu、Douglas M. Ho、Robert A. Pascal

  DOI：10.1021/jo00127a025

  日期：1995.11

  3,5-Bis(2-pyridylethynyl)-4-chloronitrobenzene (5) and 3,5-bis[[3-(4-(tert-butylbenzyl)oxy)-2-pyridyl]- ethynyl]-4-chloronitrobenzene (13) were synthesized as potential tridentate ligands, via nitrogen-chlorine donor-acceptor interactions, of 2,6-dichloropyridine and related compounds. Compound 5 was also synthesized in N-15-labeled form, and its association with 2,6-dichloropyridine, 2,6-dibromopyridine, 2,4,6-trichloropyrimidine, and 1,3-dichlorobenzene was examined by means of N-15 NMR titration experiments. The first three compounds were weakly associated with 5 (K-assoc = 0.2-0.3 M(-1)) in toluene solution and induced significant upfield shifts in its N-15 NMR resonances, but 1,3-dichlorobenzene, which cannot fit satisfactorily into the proposed ''cleft'' of compound 5, had little effect. The X-ray structure of 5 and the proposed structures of its complexes are discussed.