3-triethoxysilylpropyl-carbamic acid 1-phenyl-1-deutero-ethyl ester

• 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: 3-triethoxysilylpropyl-carbamic acid 1-phenyl-1-deutero-ethyl ester
• 英文别名: (1-deuterio-1-phenylethyl) N-(3-triethoxysilylpropyl)carbamate
• 化学式: C₁₈H₃₁NO₅Si
• 分子量: 370.525
• InChiKey: ZZGMLKONISAUPZ-QNLPYAOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氨基丙基三乙氧基硅烷 、 甲基苯甲醇-D1 、 N,N'-羰基二咪唑 在 sodium ethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以77%的产率得到3-triethoxysilylpropyl-carbamic acid 1-phenyl-1-deutero-ethyl ester
  参考文献：
  名称：

  Molecular Motion of Tethered Molecules in Bulk and Surface-Functionalized Materials:  A Comparative Study of Confinement

  摘要：

  Achieving high degrees of molecular confinement in materials is a difficult synthetic challenge that is critical for understanding supramolecular chemistry on solid surfaces and control of host-guest complexation for selective adsorption and heterogeneous catalysis. In this Article, using H-2 MAS NMR spectroscopy of tethered carbamates as a molecular probe, we systematically investigate the degree of steric confinement within three types of materials: two-dimensional silica surface, bulk amorphous microporous silica, and bulk amorphous mesoporous silica. The resulting NMR spectra are described with a simple two-site hopping model for motion and prove that the bulk silica network severely limits the molecular mobility of the immobilized carbamate at room temperature to the same degree as surface-functionalized materials at low-temperatures (similar to 210 K). Raising the temperature of the bulk materials to 413 K still demonstrates the effect of confinement, as manifested in significantly longer characteristic times for the immobilized carbamate relative to surface-functionalized materials at room temperature. The environment surrounding the carbonyl functionality of the immobilized carbamate is investigated using FT-IR spectroscopy, which shows the carbonyl stretching band to be equally shifted for all materials to lower wavenumbers relative to its noninteracting value in carbon tetrachloride solvent. These results suggest that electrostatic interactions between the carbonyl of the immobilized carbarnate and silica surface may play an important role in confining the immobilized carbarnate and nucleating the formation of a pore wall close to the immobilized carbarnate during bulk materials synthesis.

  DOI：

  10.1021/ja0556474

文献信息

• Molecular Motion of Tethered Molecules in Bulk and Surface-Functionalized Materials:  A Comparative Study of Confinement
  作者：Jessica L. Defreese、Son-Jong Hwang、A. Nicholas G. Parra-Vasquez、Alexander Katz

  DOI：10.1021/ja0556474

  日期：2006.5.1

  Achieving high degrees of molecular confinement in materials is a difficult synthetic challenge that is critical for understanding supramolecular chemistry on solid surfaces and control of host-guest complexation for selective adsorption and heterogeneous catalysis. In this Article, using H-2 MAS NMR spectroscopy of tethered carbamates as a molecular probe, we systematically investigate the degree of steric confinement within three types of materials: two-dimensional silica surface, bulk amorphous microporous silica, and bulk amorphous mesoporous silica. The resulting NMR spectra are described with a simple two-site hopping model for motion and prove that the bulk silica network severely limits the molecular mobility of the immobilized carbamate at room temperature to the same degree as surface-functionalized materials at low-temperatures (similar to 210 K). Raising the temperature of the bulk materials to 413 K still demonstrates the effect of confinement, as manifested in significantly longer characteristic times for the immobilized carbamate relative to surface-functionalized materials at room temperature. The environment surrounding the carbonyl functionality of the immobilized carbamate is investigated using FT-IR spectroscopy, which shows the carbonyl stretching band to be equally shifted for all materials to lower wavenumbers relative to its noninteracting value in carbon tetrachloride solvent. These results suggest that electrostatic interactions between the carbonyl of the immobilized carbarnate and silica surface may play an important role in confining the immobilized carbarnate and nucleating the formation of a pore wall close to the immobilized carbarnate during bulk materials synthesis.