1-tert-butyl-1-(4-methylphenyl)methyl bromide | 251967-27-8

• 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: 1-tert-butyl-1-(4-methylphenyl)methyl bromide
• 英文别名: 1-(1-Bromo-2,2-dimethylpropyl)-4-methylbenzene
• CAS: 251967-27-8
• 化学式: C₁₂H₁₇Br
• 分子量: 241.171
• InChiKey: JOWCTIPHJIUIGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,2-dimethyl-1-(4-methylphenyl)propan-1-ol 在 三溴化磷 作用下， 生成 1-tert-butyl-1-(4-methylphenyl)methyl bromide
  参考文献：
  名称：

  Solvolysis of 1-Aryl-1-tert-butylmethyl Bromides. Hammett-Type Correlation Analysis and RevisedY_BnBrScale

  摘要：

  AbstractThe solvolysis of a series of 1‐aryl‐1‐tert‐butylmethyl bromides (1a–1g) in a variety of solvents were carried out. Linear relationships were observed from Hammett‐type analysis of logarithm of rate constants using single‐parameter Brown‐Okamoto equation (Eqn. 1) and dual‐parameter Yukawa‐Tsuno equation (Eqn. 2), respectively. The ρ values and the γ values were found to depend mainly on the range of substituents and not the type of solvents employed. The observation of an upward deviation for the data points of strongly deactivating substrates 1f and 1g could be interpreted by an electrophilic acceleration owing to the solvation of leaving group. It is likely an additional example of overshadowed solvent effect in the dual‐parameter treatment of rate data. Moreover, the variation of γ values was found contradicting the general consideration of resonance contribution. The observed excellent linear correlations with YBnBr and the good solubility in aqueous solution with high percentage of water made 1c a better reference standard than 2‐bromo‐2‐(4‐trifluormethyl)adamantane (3) for obtaining revised and extended YBnBr values. Correlation analysis using the single‐parameter Grunwald‐Winstein equation (Eqn. 3) with YBnBr was found to be superior over the dual‐parameter equation containing YBr and I (Eqn. 5).

  DOI：

  10.1002/jccs.199900107

文献信息

• Solvolysis of 1-Aryl-1-<i>tert</i>-butylmethyl Bromides. Hammett-Type Correlation Analysis and Revised<i>Y</i>_BnBrScale
  作者：Kwang-Ting Liu、Chin-Pu Chin、Der-Gann Yu、Yeh-Fang Duann

  DOI：10.1002/jccs.199900107

  日期：1999.10

  AbstractThe solvolysis of a series of 1‐aryl‐1‐tert‐butylmethyl bromides (1a–1g) in a variety of solvents were carried out. Linear relationships were observed from Hammett‐type analysis of logarithm of rate constants using single‐parameter Brown‐Okamoto equation (Eqn. 1) and dual‐parameter Yukawa‐Tsuno equation (Eqn. 2), respectively. The ρ values and the γ values were found to depend mainly on the range of substituents and not the type of solvents employed. The observation of an upward deviation for the data points of strongly deactivating substrates 1f and 1g could be interpreted by an electrophilic acceleration owing to the solvation of leaving group. It is likely an additional example of overshadowed solvent effect in the dual‐parameter treatment of rate data. Moreover, the variation of γ values was found contradicting the general consideration of resonance contribution. The observed excellent linear correlations with YBnBr and the good solubility in aqueous solution with high percentage of water made 1c a better reference standard than 2‐bromo‐2‐(4‐trifluormethyl)adamantane (3) for obtaining revised and extended YBnBr values. Correlation analysis using the single‐parameter Grunwald‐Winstein equation (Eqn. 3) with YBnBr was found to be superior over the dual‐parameter equation containing YBr and I (Eqn. 5).