3,3-dibromo-1-(phenyl)propan-1-one | 41949-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dibromo-1-(phenyl)propan-1-one
• 英文别名: β,β-Dibromethylphenylketon；3,3-Dibromo-1-phenylpropan-1-one；3,3-dibromo-1-phenylpropan-1-one
• CAS: 41949-29-5
• 化学式: C₉H₈Br₂O
• 分子量: 291.97
• InChiKey: AMAHRIMDNLTTOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-dibromo-1-(phenyl)propan-1-one 在 sodium azide 作用下， 以 甲醇 、 氘代氯仿 、 水 、 丙酮 为溶剂， 反应 25.0h， 生成 苯甲酰乙腈
  参考文献：
  名称：

  Cracking under Internal Pressure: Photodynamic Behavior of Vinyl Azide Crystals through N₂ Release

  摘要：

  When exposed to UV light, single crystals of the vinyl azides 3-azido-1-phenylpropenone (1a), 3-azido-1-(4-methoxypheny0propenone (1b), and 3-azido-1-(4-chlorophenyl)propenone (1c) exhibit dramatic mechanical effects by cracking or bending with the release of N-2. Mechanistic studies using laser flash photolysis, supported by quantum mechanical calculations, show that each of the vinyl azides degrades through a vinylnitrene intermediate. However, despite having very similar crystal packing motifs, the three compounds exhibit distinct photomechanical responses in bulk crystals. While the crystals of la delaminate and release gaseous N-2 indiscriminately under paraffin oil, the crystals of lb and 1c visibly expand, bend, and fracture, mainly along specific crystallographic faces, before releasing N-2. The photochemical analysis suggests that the observed expansion is due to internal pressure exerted by the gaseous product in the crystal lattices of these materials. Lattice energy calculations, supported by nanoindentation experiments, show significant differences in the respective lattice energies. The calculations identify critical features in the crystal structures of 1b and 1c where elastic energy accumulates during gas release, which correspond to the direction of the observed cracks. This study highlights the hitherto untapped potential of photochemical gas release to elicit a photomechanical response and motility of photoreactive molecular crystals.

  DOI：

  10.1021/jacs.0c07830
• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 在 Jones reagent 、 silica gel 、 三溴化磷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.67h， 生成 3,3-dibromo-1-(phenyl)propan-1-one
  参考文献：
  名称：

  Cracking under Internal Pressure: Photodynamic Behavior of Vinyl Azide Crystals through N₂ Release

  摘要：

  When exposed to UV light, single crystals of the vinyl azides 3-azido-1-phenylpropenone (1a), 3-azido-1-(4-methoxypheny0propenone (1b), and 3-azido-1-(4-chlorophenyl)propenone (1c) exhibit dramatic mechanical effects by cracking or bending with the release of N-2. Mechanistic studies using laser flash photolysis, supported by quantum mechanical calculations, show that each of the vinyl azides degrades through a vinylnitrene intermediate. However, despite having very similar crystal packing motifs, the three compounds exhibit distinct photomechanical responses in bulk crystals. While the crystals of la delaminate and release gaseous N-2 indiscriminately under paraffin oil, the crystals of lb and 1c visibly expand, bend, and fracture, mainly along specific crystallographic faces, before releasing N-2. The photochemical analysis suggests that the observed expansion is due to internal pressure exerted by the gaseous product in the crystal lattices of these materials. Lattice energy calculations, supported by nanoindentation experiments, show significant differences in the respective lattice energies. The calculations identify critical features in the crystal structures of 1b and 1c where elastic energy accumulates during gas release, which correspond to the direction of the observed cracks. This study highlights the hitherto untapped potential of photochemical gas release to elicit a photomechanical response and motility of photoreactive molecular crystals.

  DOI：

  10.1021/jacs.0c07830

文献信息

• Cracking under Internal Pressure: Photodynamic Behavior of Vinyl Azide Crystals through N₂ Release
  作者：Dylan J. Shields、Durga Prasad Karothu、Karthik Sambath、Ranaweera A. A. Upul Ranaweera、Stefan Schramm、Alexander Duncan、Benjamin Duncan、Jeanette A. Krause、Anna D. Gudmundsdottir、Panče Naumov

  DOI：10.1021/jacs.0c07830

  日期：2020.10.28

  When exposed to UV light, single crystals of the vinyl azides 3-azido-1-phenylpropenone (1a), 3-azido-1-(4-methoxypheny0propenone (1b), and 3-azido-1-(4-chlorophenyl)propenone (1c) exhibit dramatic mechanical effects by cracking or bending with the release of N-2. Mechanistic studies using laser flash photolysis, supported by quantum mechanical calculations, show that each of the vinyl azides degrades through a vinylnitrene intermediate. However, despite having very similar crystal packing motifs, the three compounds exhibit distinct photomechanical responses in bulk crystals. While the crystals of la delaminate and release gaseous N-2 indiscriminately under paraffin oil, the crystals of lb and 1c visibly expand, bend, and fracture, mainly along specific crystallographic faces, before releasing N-2. The photochemical analysis suggests that the observed expansion is due to internal pressure exerted by the gaseous product in the crystal lattices of these materials. Lattice energy calculations, supported by nanoindentation experiments, show significant differences in the respective lattice energies. The calculations identify critical features in the crystal structures of 1b and 1c where elastic energy accumulates during gas release, which correspond to the direction of the observed cracks. This study highlights the hitherto untapped potential of photochemical gas release to elicit a photomechanical response and motility of photoreactive molecular crystals.