perchloroacenaphthylene | 7267-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 吖萘类
• 英文名称: perchloroacenaphthylene
• 英文别名: octachloroacenaphthylene；Acenaphthylene, octachloro-；1,2,3,4,5,6,7,8-octachloroacenaphthylene
• CAS: 7267-16-5
• 化学式: C₁₂Cl₈
• 分子量: 427.756
• InChiKey: ZAFNYNRBTOVYPF-UHFFFAOYSA-N

物化性质

• 熔点：
  375 °C
• 沸点：
  505.9±50.0 °C(Predicted)
• 密度：
  1.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  perchloroacenaphthylene 以 neat (no solvent) 为溶剂， 生成 足球烯
  参考文献：
  名称：

  Formation of Buckminsterfullerene and Its Perchlorinated Fragments by Laser Ablation of Perchloroacenaphthylene

  摘要：

  Perchloroacenaphthylene(C12Cl8), a perchlorinated polycyclic hydrocarbon composed of two hexagons and a pentagon, was ablated by a pulsed laser beam in a vacuum. The products created from the laser ablation were characterized by high-performance liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry and rapid-scan ultraviolet spectrophotometric detection. Buckminsterfullerene C-60 and various perchlorinated carbon clusters have been observed among the products. The observation is helpful for understanding the formation mechanisms of fullerenes and suggests that the Pentagon Road scheme is feasible with the involvement of chlorines.

  DOI：

  10.1021/jp0012395
• 作为产物：
  描述：

  苊 在 五氯化磷 、 三苯基膦 作用下， 以 氯苯 为溶剂， 反应 16.0h， 生成 perchloroacenaphthylene
  参考文献：
  名称：

  全氯苯二烯基自由基

  摘要：

  我们报告了全氯苯烯基自由基的制备和固态表征 (1)。该自由基最初是通过还原全氯苯鎓盐 (12(+)) 获得的黄绿色固体。该固体在密封管中升华，得到全氯苯二烯基 (1) 的黑色闪亮六方晶体。该结构由单体自由基的一维堆叠组成。周围氯原子迫使苯烯基系统成为强烈非平面的，导致堆叠内相邻分子之间的大间隔 (3.78 A)，并且分子采用两个不同的堆叠基序（准叠加并相对于相邻分子旋转 60 度）。由于晶格中的堆积挫折和较大的分子间间距，固体在 100-400 K 的温度范围内表现出居里顺磁性，在低温下反铁磁耦合开始之前。由于单个分子的隔离产生的窄带宽，固体是莫特-哈伯德绝缘体，室温电导率为 rho(RT) = 10(-10) S/cm。

  DOI：

  10.1021/ja0018015

文献信息

• Preparation of Decachlorocorannulene and Other Perchlorinated Fragments of Fullerenes by Electrical Discharge in Liquid Chloroform
  作者：Rongbin Huang、Weijie Huang、Yuhuang Wang、Zichao Tang、Lansun Zheng

  DOI：10.1021/ja970238w

  日期：1997.6.1

  地址: 1. XIAMEN UNIV, DEPT CHEM, STATE KEY LAB PHYS CHEM SOLID SURFACE, XIAMEN 361005, FUJIAN PEOPLES R CHINA

  地址: 1. 厦门大学化学系国家重点实验室物理化学固体表面, 厦门 361005, 福建人民 R 中国
• Glow discharge synthesis and molecular structures of perchlorofluoranthene and other perchlorinated fragments of buckminsterfullerene
  作者：Su-Yuan Xie、Rong-Bin Huang、Li-Hua Chen、Wei-Jie Huang、Lan-Sun Zheng

  DOI：10.1039/a806160b

  日期：——

  A series of perchlorinated fragments of buckminsterfullerene were prepared by glow discharge using chloroform vapor; their structural features are of significance in understanding the formation mechanism of fullerenes.

  利用氯仿蒸汽通过辉光放电制备了一系列龅牙匠富勒烯的高氯碎片；它们的结构特征对于了解富勒烯的形成机理具有重要意义。
• Crystal Structure of 4,7-Dichloro-1,2,3,5,6,8-hexakis-(4-methoxy-phenylsulfanyl)-acenaphthylene
  作者：Shun-Liu Deng、Sa Li、Rong-Bin Huang、Lan-Sun Zheng

  DOI：10.1007/s10870-008-9373-3

  日期：2008.9

  The title compound was prepared from the reaction of perchloroacenaphthylene with an excess of sodium salt of 4-methyloxythiophenol in toluene/ethanol (1:1) solvent and structurally characterized by single-crystal X-ray diffraction. The compound crystallizes in the Monoclinic space group P2(1) with the parameters: a = 10.351(1) Å, b = 20.453(3) Å, c = 12.1837(16) Å, β = 105.584(3)°, V = 2484.5(6) Å3, with Z = 2 formula units. The title compound 4,7-dichloro-1,2,3,5,6,8-hexakis-(4-methoxy-phenylsulfanyl)-acenaphthylene was synthesized from perchloroacenaphthylene C 12 Cl 8 with an excess of 4-methoxybenzene thiolate in toluene/ethanol (1:1) .

  标题化合物由全氯苊烯与过量的4-甲基氧基苯硫酚钠盐在甲苯/乙醇（1:1）溶剂中的反应制备而成，并通过单晶X射线衍射确定了其结构。该化合物在单斜晶系空间群P2(1)中结晶，其参数为：a=10.351(1)Å，b=20.453(3)Å，c=12.1837(16)Å，β=105.584(3)°，V=2484.5(6)Å3，Z=2个公式单元。标题化合物4,7-二氯-1,2,3,5,6,8-六（4-甲氧基苯硫基）苊烯由全氯苊烯C 12 Cl 8与过量的4-甲氧基苯硫醇在甲苯/乙醇（1:1）中合成。
• Formation of octachloroacenaphthylene in the pyrolysis of decachlorobiphenyl
  作者：A. Bleise、E. Kleist、K. Günther、M.J. Schwuger

  DOI：10.1016/s0045-6535(97)00110-0

  日期：1997.8

  The pyrolytic degradation of decachlorobiphenyl (PCB 209) in the temperature range of 700 - 1000 degrees C and at a pyrolysis time of 10 seconds generated one main chloroaromatic product. This compound has been identified by HPLC-UV, GC-MS, GC-FTIR and C-13-NMR as octachloroacenaphthylene (OCAN).The mechanism of the nearly quantitative formation of octachloroacenaphthylene (OCAN) occurs via a nonachlorobenzobarrylene radical (ZIR) as an intermediate followed by a rearrangement and further dechlorination to form OCAN, Calculations with the program THERM based on the Benson-group-theory indicated that this mechanism is not possible for lower or nonchlorinated biphenyls. (C) 1997 Elsevier Science Ltd.
• Dodecachlorotetracyclo[7.2.1.02,8.05,12]dodeca-3,6,10-triene, a fully chlorinated valence isomer of [12]annulene
  作者：V. N. Mallikarjuna Rao、Catherine J. Hurt、Kousuke Kusuda、Joseph C. Calabrese、Robert West

  DOI：10.1021/ja00856a030

  日期：1975.11