O-salicylbenzamidoxime | 134817-09-7

• 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: O-salicylbenzamidoxime
• 英文别名: N^2^-(2-Hydroxybenzoyloxy)benzamidine；[(Z)-[amino(phenyl)methylidene]amino] 2-hydroxybenzoate
• CAS: 134817-09-7
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: CDYSRHBAYVOGCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-salicylbenzamidoxime 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 22.0h， 以98%的产率得到2-(3-phenyl-1,2,4-oxadiazol-5-yl) phenol
  参考文献：
  名称：

  双功能分子的激发态酸度。2. 5-（2-羟苯基）-3-苯基-1,2,4-恶二唑的皮秒发射

  摘要：

  5-(2-Hydroxyphenyl)-3-phenyl-1,2,4-oxadiazole has been synthesized in high yields and the kinetics of its intramolecular proton-transfer process has been investigated by using steady-state and time-dependent picosecond laser spectroscopy. On the basis of these experimental determinations and the results of quantum-mechanical calculations, the structures of the two fluorescing species observed have been assigned to two different conformations of the same molecular structure, both being present in the ground state. Rapid proton transfer in the excited state is suggested as the predominant quenching process of one of these conformations.

  DOI：

  10.1021/j100170a031
• 作为产物：
  描述：

  苯甲酰胺肟 、 水杨酰氯 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以95%的产率得到O-salicylbenzamidoxime
  参考文献：
  名称：

  双功能分子的激发态酸度。2. 5-（2-羟苯基）-3-苯基-1,2,4-恶二唑的皮秒发射

  摘要：

  5-(2-Hydroxyphenyl)-3-phenyl-1,2,4-oxadiazole has been synthesized in high yields and the kinetics of its intramolecular proton-transfer process has been investigated by using steady-state and time-dependent picosecond laser spectroscopy. On the basis of these experimental determinations and the results of quantum-mechanical calculations, the structures of the two fluorescing species observed have been assigned to two different conformations of the same molecular structure, both being present in the ground state. Rapid proton transfer in the excited state is suggested as the predominant quenching process of one of these conformations.

  DOI：

  10.1021/j100170a031

文献信息

• Three<i>N</i>²-benzoyloxybenzamidines: sheet structures built from hard and soft hydrogen bonds and aromatic π–π stacking interactions
  作者：Carlos E. M. Carvalho、Solange M. S. V. Wardell、James L. Wardell、Janet M. S. Skakle、John N. Low、Christopher Glidewell

  DOI：10.1107/s0108270103025435

  日期：2004.1.15

  Molecules of the title compounds N-2-( benzoyloxy) benzamidine, C14H12N2O2, ( I), N-2-( 2- hydroxybenzoyloxy) benzamidine, C14H12N2O3, ( II), and N-2- benzoyloxy- 2- hydroxybenzamidine, C14H12N2O3, ( III), all have extended chain conformations, with the aryl groups remote from one another. In ( I), the molecules are linked into chains by a single N - H ... N hydrogen bond [H ... N = 2.15 Angstrom, N ... N = 3.029 (2) Angstrom and N - H ... N = 153degrees] and these chains are linked into sheets by means of aromatic pi - pi stacking interactions. There is one intramolecular O - H ... O hydrogen bond in ( II), and a combination of one three-centre N - H ...( N, O) hydrogen bond [H ... N = 2.46 Angstrom, H ... O = 2.31 Angstrom, N ... N = 3.190 ( 2) Angstrom, N ... O = 3.146 ( 2) Angstrom, N - H ... N = 138degrees and N - H ... O = 154degrees] and one two- centre C - H ... O hydrogen bond [H ... O = 2.46 Angstrom, C ... O = 3.405 (2) Angstrom and C - H ... O = 173degrees] links the molecules into sheets. In ( III), an intramolecular O H H ... N hydrogen bond and two N - H ... O hydrogen bonds [H ... O = 2.26 and 2.10 Angstrom, N ... O = 2.975 ( 2) and 2.954 ( 2) Angstrom, and N - H ... O = 138 and 163degrees] link the molecules into sheets.
• Excited-state acidity of bifunctional molecules. 2. Picosecond emission of 5-(2-hydroxyphenyl)-3-phenyl-1,2,4-oxadiazole
  作者：Ira M. Brinn、Carlos Eduardo M. Carvalho、Francine Heisel、Joseph Albert Miehe

  DOI：10.1021/j100170a031

  日期：1991.8

  5-(2-Hydroxyphenyl)-3-phenyl-1,2,4-oxadiazole has been synthesized in high yields and the kinetics of its intramolecular proton-transfer process has been investigated by using steady-state and time-dependent picosecond laser spectroscopy. On the basis of these experimental determinations and the results of quantum-mechanical calculations, the structures of the two fluorescing species observed have been assigned to two different conformations of the same molecular structure, both being present in the ground state. Rapid proton transfer in the excited state is suggested as the predominant quenching process of one of these conformations.