1,1-Dimethylallylradikal | 60288-52-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,1-Dimethylallylradikal
• 英文别名: 3-methyl-but-1->3-enyl；3-methyl-2-butenyl radical；3-Methyl-2-butenyl
• CAS: 60288-52-0
• 化学式: C₅H₉
• 分子量: 69.1265
• InChiKey: ICPOKTZORRQGLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1,1-Dimethylallylradikal 生成 天然橡胶
  参考文献：
  名称：

  Homolytic Bond Dissociation Enthalpies of the C−H Bonds Adjacent to Radical Centers

  摘要：

  Homolytic bond dissociation enthalpies (BDEs) at 0 and 298 K of the C-H bonds adjacent to various radical centers have been obtained from ab initio CBS-4 (complete basis set) model calculations and experimental data available in the literature. The BDEs of the C-H bonds adjacent to the radical centers derived from 11 saturated hydrocarbons were found to be 33.5 +/- 3 kcal/mol at 298 K. The BDEs of the C-H bonds adjacent to nine allylic and benzylic radical centers were found to be 48 +/- 3 kcal/mol at 298 K, but the benzylic C-H BDE of the PhCH2CH2. radical was found to be only 29.7 and 30.5 kcal/mol at 0 and 298 K, respectively. The BDEs of the vinylic C-H bonds adjacent to four vinylic radical centers were found to be 35.5 +/- 3.5 kcal/mol at 298 K. The BDEs of the vinylic C-H bonds adjacent to three allylic radical centers were found to be 56.5 +/- 3 kcal/mol at 298 K. These results suggest that the radical centers weaken the adjacent C-H bond strengths by about 50-70 kcal/mol. The calculated BDEs agree within +/-2 kcal/mol with most of the available experimental results. Isomerization enthalpies of butenes and pentenes have been obtained. Substituent effects on BDEs have also been examined.

  DOI：

  10.1021/jo971768d
• 作为产物：
  描述：

  3,3,6-三甲基庚-1,5-二烯 生成 1,1-Dimethylallylradikal
  参考文献：
  名称：

  Roth, Wolfgang R.; Staemmler, Volker; Neumann, Martin, Liebigs Annalen, 1995, # 6, p. 1061 - 1118

  摘要：

  DOI：

文献信息

• Time-resolved observation of sequential bond cleavage in a gas-phase azoalkane
  作者：J. Stephen. Adams、Katherine A. Burton、B. Kim. Andrews、R. Bruce. Weisman、Paul S. Engel

  DOI：10.1021/ja00285a009

  日期：1986.12
• ——
  作者：A. V. Voronenkov、N. A. Simonov、O. P. Yablonskii、S. G. Koshel'、V. V. Voronenkov

  DOI：10.1023/a:1012359819642

  日期：——

  Products of liquid-phase oxidation of 2-methyl-2-butene and 2-methyl-2-pentene were studied by NMR and IR spectroscopy. Steric hindrances in liquid-phase oxidation of olefins with iso structure were shown to arise from branching of the alkyl group at the alpha -carbon atom.
• Cuthbertson, Matthew J.; Rizzardo, Ezio; Solomon, David H., Australian Journal of Chemistry, 1983, vol. 36, # 10, p. 1957 - 1973
  作者：Cuthbertson, Matthew J.、Rizzardo, Ezio、Solomon, David H.

  DOI：——

  日期：——
• Roth, Wolfgang R.; Staemmler, Volker; Neumann, Martin, Liebigs Annalen, 1995, # 6, p. 1061 - 1118
  作者：Roth, Wolfgang R.、Staemmler, Volker、Neumann, Martin、Schmuck, Carsten

  DOI：——

  日期：——
• Homolytic Bond Dissociation Enthalpies of the C−H Bonds Adjacent to Radical Centers
  作者：Xian-Man Zhang

  DOI：10.1021/jo971768d

  日期：1998.3.1

  Homolytic bond dissociation enthalpies (BDEs) at 0 and 298 K of the C-H bonds adjacent to various radical centers have been obtained from ab initio CBS-4 (complete basis set) model calculations and experimental data available in the literature. The BDEs of the C-H bonds adjacent to the radical centers derived from 11 saturated hydrocarbons were found to be 33.5 +/- 3 kcal/mol at 298 K. The BDEs of the C-H bonds adjacent to nine allylic and benzylic radical centers were found to be 48 +/- 3 kcal/mol at 298 K, but the benzylic C-H BDE of the PhCH2CH2. radical was found to be only 29.7 and 30.5 kcal/mol at 0 and 298 K, respectively. The BDEs of the vinylic C-H bonds adjacent to four vinylic radical centers were found to be 35.5 +/- 3.5 kcal/mol at 298 K. The BDEs of the vinylic C-H bonds adjacent to three allylic radical centers were found to be 56.5 +/- 3 kcal/mol at 298 K. These results suggest that the radical centers weaken the adjacent C-H bond strengths by about 50-70 kcal/mol. The calculated BDEs agree within +/-2 kcal/mol with most of the available experimental results. Isomerization enthalpies of butenes and pentenes have been obtained. Substituent effects on BDEs have also been examined.