2-{2-(dimethylaminomethyl)phenyl}-4,4-diphenyl-1,3,2-dioxaborolane | 80155-06-2

• 英文名称: 2-{2-(dimethylaminomethyl)phenyl}-4,4-diphenyl-1,3,2-dioxaborolane
• CAS: 80155-06-2
• 化学式: C₂₃H₂₄BNO₂
• 分子量: 357.26
• InChiKey: ZORACEUPJLEACU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  1,1-二苯基乙烷-1,2-二醇 、 2-(dimethylaminomethyl)benzeneboronic anhydride 以 甲苯 为溶剂， 以74%的产率得到2-{2-(dimethylaminomethyl)phenyl}-4,4-diphenyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Burgemeister, Thomas; Grobe-Einsler, Ronald; Grotstollen, Reiner, Chemische Berichte, 1981, vol. 114, # 10, p. 3403 - 3411

  摘要：

  DOI：

文献信息

• Dynamic NMR as a Nondestructive Method for the Determination of Rates of Dissociation. XVII. Dissociation of the N–B Bond in the Coordinated Form of 2-[2-(Dimethylaminomethyl)phenyl]-4,4-diphenyl-1,3,2-dioxaborolane and Related Compounds
  作者：Shinji Toyota、Michinori Oki

  DOI：10.1246/bcsj.63.1168

  日期：1990.4

  The rates of dissociation of the N–B bonds in the title compounds were reexamined by the dynamic NMR technique to get further insight into the mechanism of dissociation. Entropies of activation were fairly large positive to suggest that the dissociation of a bond of ionic characters is the rate-limiting step. The rates of dissociation were generally larger in nonpolar solvents than in polar solvents, suggesting that the stabilization of the ground state by solvation was important in determining the activation energy for dissociation. Diethyl ether, tetrahydrofuran, and acetone gave larger rate constants of dissociation than those expected from their polarity. Participation of solvent molecules in the dissociation is discussed on the basis of these results. Introduction of various substituents indicated that steric effects as well as electronic effects affect the N–B bond energy.

  我们利用动态核磁共振技术重新研究了标题化合物中 N-B 键的解离速率，以进一步了解解离机制。活化熵相当大，表明离子性键的解离是限速步骤。非极性溶剂中的解离速率通常大于极性溶剂中的解离速率，这表明溶解对基态的稳定在决定解离活化能方面起着重要作用。二乙醚、四氢呋喃和丙酮的解离速率常数大于根据其极性所预期的速率常数。根据这些结果对溶剂分子参与解离进行了讨论。引入各种取代基表明，立体效应和电子效应都会影响 N-B 键的能量。