2-hydroxy-1-(2'-propylthiophenylazo)naphthalene | 1374558-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-1-(2'-propylthiophenylazo)naphthalene
• 英文别名: 2-hydroxy-1-(2′-(n-propyl)thiophenylazo)naphthalene；1-[(2-Propylsulfanylphenyl)diazenyl]naphthalen-2-ol
• CAS: 1374558-40-3
• 化学式: C₁₉H₁₈N₂OS
• 分子量: 322.431
• InChiKey: YYQHFTXUMWEAOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1-(2'-propylthiophenylazo)naphthalene 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 [Pt(2-oxy-1-(2′-(n-propyl)thiophenylazo)naphthalene)I]
  参考文献：
  名称：

  Synthesis, characterization, X-ray structure and spectroscopic study of platinum(II) complexes with tridentate diazene ligands having O,N,S donor set

  摘要：

  At room temperature, 2-hydroxy-1-(2'-alkylthiophenylazo)naphthalenes and 1-hydroxy-2-(2'-alkylthiophenylazo)napthalenes (HL) slowly react with di-mu-chloro-bis(eta(3)-2-methylallyl)platinum(II) in chloroform and afford complexes of the type [Pt-II(L) Cl]. Potassium tetrachloroplatinate also reacts with the HL group of ligands in acetonitrile medium under reflux condition and produces complexes of the type [Pt-II (L)Cl]. All the platinum complexes [Pt-II(L)Cl] have been successfully isolated in pure form and characterized by spectroscopic techniques. The solid state structures of [Pt-II(L-3)Cl] (3) and [Pt-II(L-9)Cl] (9) have been determined by single crystal X-ray diffraction. The crystal structures have revealed that diazene ligands bind to the metal ion as monoanionic terdentate O,N,S donors and the fourth coordination position is occupied by a halide ion. All the platinum(II) complexes absorb strongly in the ultraviolet and visible region. The TD-DFT (time-dependent density functional theory) calculation has been carried out for better understanding of the electronic structure of platinum(II) complexes and the nature of spectral transitions. The low energy absorptions are attributed to intraligand charge transfer transitions having admixtures of metal-to-ligand charge-transfer transitions whereas the high energy absorptions are due to ILCT and LLCT transitions. The reactivity of [Pt-II(L) Cl] with iodine and methyl iodide has been studied. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.09.041
• 作为产物：
  描述：

  2-(硫代丙基)苯胺 1盐酸盐 、 2-萘酚 在 亚硝基硫酸 作用下， 以38%的产率得到2-hydroxy-1-(2'-propylthiophenylazo)naphthalene
  参考文献：
  名称：

  Palladium(II) complexes of terdentate azo ligands with an O,N,S donor set: Synthesis, spectroscopic characterization, X-ray structure and TD-DFT calculations

  摘要：

  The reaction of 2-hydroxy-1-(2'-alkylthiophenylazo)naphthalenes (HL1-HL5) and 1-hydroxy-2-(2'-alkylthiophenylazo)naphthalenes (HL6-HL10) with sodium tetrachloropalladate in ethanol medium at room temperature leads to the formation of a new series of complexes of the type [Pd(L)Cl]. All the palladium compounds have been isolated in their pure form and characterized by spectral and elemental analysis data. The crystal structures of [(PdLCl)-Cl-3] (3) and [(PdLCl)-Cl-6] (6) have been determined by single crystal Xray diffraction as representative cases. The crystal structures show that both complexes have distorted square-planar structures in which he palladium(II) centers are bonded to O1 of the naphtholato function, N2 of the diazene group and Si at the 2' position of the phenyl fragment. Therefore, the ligands bind palladium(II) in a tridentate monoanionic [O, N, S] fashion, which give rise to five- and six-membered chelate rings in each case. The fourth coordination site is occupied by a chloride ion. These complexes show intense absorption bands in the visible and UV region. The nature of the electronic transitions has been examined using (TD-DFT) formalism. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.02.021