Perchloro-2-methylnaphthalene | 150986-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Perchloro-2-methylnaphthalene
• 英文别名: 1,2,3,4,5,6,8-heptachloro-7-(trichloromethyl)naphthalene
• CAS: 150986-19-9
• 化学式: C₁₁Cl₁₀
• 分子量: 486.651
• InChiKey: MAIQPUMBTHGCAF-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C(Solvent: Hexane)
• 沸点：
  494.4±40.0 °C(predicted)
• 密度：
  1.882±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  Perchloro-2-methylnaphthalene 在 硫酸 作用下， 反应 6.0h， 以88%的产率得到Heptachloro-2-naphthoic acid
  参考文献：
  名称：

  Perchloro-2-methylnaphthalene, a Novel Chlorocarbon with a Highly Strained Structure

  摘要：

  Perchloro-2-methylnaphthalene (1) is prepared in a two-step reaction: treatment of 2H-heptachloronaphthalene (3) with CCl3F in the presence of AlCl3 yields heptachloro-7-(trifluoromethyl)naphthalene (4), which in CS2 and with an excess of AlCl3 affords 1. The spectra and X-ray crystal structure of chlorocarbon 1 are reported, as well as that of the much less strained heptachloro-7-(dichloromethyl)naphthalene (10). The unusual UV spectrum, due to the distortion of the aromatic rings, is also discussed. The reduction of 1 with copper wire to give perchloro(2-naphthyl)methyl radical (11) has been studied by means of electron spin resonance. Steric inhibition to resonance of the free electron within the aromatic ring in 11 has been estimated by a semiempirical AM1 method.

  DOI：

  10.1021/jo00114a019
• 作为产物：
  描述：

  2-甲基萘 在 二氯化二硫 、 三氯化铝 、 磺酰氯 作用下， 反应 4.0h， 以45%的产率得到Perchloro-2-methylnaphthalene
  参考文献：
  名称：

  Application of thermal kinetics to small carbon ion clusters

  摘要：

  Kinetic energy release distributions (KERDS') were obtained experimentally for unimolecular decomposition of small carbon ion clusters C(n)+, n = 10-13 and 18, made by dissociative ionization from perchloro conjugated hydrocarbons. A model-free approach due to Klots, based on the application of thermal kinetics to small systems, allowed the extraction of binding energies for these clusters. The results were found to be in very good agreement with literature values for collisionally activated dissociation (CAD) threshold energies. The ion C-11+ demonstrates a particularly high binding energy in agreement with its magic character in C(n)+ mass spectra, while C-13+ has a relatively low binding energy, reflected in its low abundance in such spectra.

  DOI：

  10.1021/j100127a006

文献信息

• Ion/molecule reactions of carbon cluster ions and acrylonitrile
  作者：Jing Sun、Hans F. Gruetzmacher、Chava Lifshitz

  DOI：10.1021/ja00071a054

  日期：1993.9

  cluster ions (C(n).+, n = 10-18 and 20) in the gas phase with acrylonitrile (ACN) as the neutral reagent were investigated by Fourier transform ion cyclotron resonance spectrometry (FT-ICR). The carbon cluster ions studied were generated by electron impact ionization of perchlorinated polyaromatic compounds (PPA) and subsequent exhaustive chlorine elimination in the external ion source of the FT-ICR spectrometer

  通过傅里叶变换离子回旋共振光谱法 (FT-ICR) 研究了以丙烯腈 (ACN) 为中性试剂的气相中碳簇离子 (C(n).+, n = 10-18 和 20) 的离子/分子反应）。研究的碳簇离子是通过高氯多环芳烃化合物 (PPA) 的电子碰撞电离和随后在 FT-ICR 光谱仪的外部离子源中彻底消除氯产生的。前体 PPA 是通过使用 BMC 试剂氯化适当的多环芳烃来制备的。对 C(n).+ 观察到的唯一反应是形成通过辐射缔合稳定的加合离子（对于 n = 10-18 和 20），但 C-16.+ 除外，它通过失去中性来稳定加合离子C3. C(n).+ 与 ACN 反应的速率常数从 k(bi) = < 10(-13) cm3 分子-1 s-1 (C18.+, C20.+) 到 k(bi) = 7.1 x 10(-10) cm3 分子-1 s-1 (C-13.+) 并且是明显大于之前研究的 HCN 和
• Application of thermal kinetics to small carbon ion clusters
  作者：Chava Lifshitz、Pablo Sandler、Hans Friedrich Gruetzmacher、Jing Sun、Thomas Weiske、Helmut Schwarz

  DOI：10.1021/j100127a006

  日期：1993.6

  Kinetic energy release distributions (KERDS') were obtained experimentally for unimolecular decomposition of small carbon ion clusters C(n)+, n = 10-13 and 18, made by dissociative ionization from perchloro conjugated hydrocarbons. A model-free approach due to Klots, based on the application of thermal kinetics to small systems, allowed the extraction of binding energies for these clusters. The results were found to be in very good agreement with literature values for collisionally activated dissociation (CAD) threshold energies. The ion C-11+ demonstrates a particularly high binding energy in agreement with its magic character in C(n)+ mass spectra, while C-13+ has a relatively low binding energy, reflected in its low abundance in such spectra.
• Perchloro-2-methylnaphthalene, a Novel Chlorocarbon with a Highly Strained Structure
  作者：J. Carilla、Ll. Fajari、R. Garcia、L. Julia、C. Marcos、J. Riera、C. R. Whitaker、J. Rius、C. Aleman

  DOI：10.1021/jo00114a019

  日期：1995.5

  Perchloro-2-methylnaphthalene (1) is prepared in a two-step reaction: treatment of 2H-heptachloronaphthalene (3) with CCl3F in the presence of AlCl3 yields heptachloro-7-(trifluoromethyl)naphthalene (4), which in CS2 and with an excess of AlCl3 affords 1. The spectra and X-ray crystal structure of chlorocarbon 1 are reported, as well as that of the much less strained heptachloro-7-(dichloromethyl)naphthalene (10). The unusual UV spectrum, due to the distortion of the aromatic rings, is also discussed. The reduction of 1 with copper wire to give perchloro(2-naphthyl)methyl radical (11) has been studied by means of electron spin resonance. Steric inhibition to resonance of the free electron within the aromatic ring in 11 has been estimated by a semiempirical AM1 method.