1-hydroxy-2-(2'-methylthiophenylazo)naphthalene | 1374558-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-hydroxy-2-(2'-methylthiophenylazo)naphthalene
• 英文别名: 2-[(2-Methylsulfanylphenyl)diazenyl]naphthalen-1-ol
• CAS: 1374558-42-5
• 化学式: C₁₇H₁₄N₂OS
• 分子量: 294.377
• InChiKey: ZRZGNKZBDCFQHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1-hydroxy-2-(2'-methylthiophenylazo)naphthalene 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 [Pt(1-oxy-2-(2'-methylthiophenylazo)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-氨基苯硫醇 在 亚硝基硫酸 、 sodium methylate 作用下， 反应 3.0h， 生成 1-hydroxy-2-(2'-methylthiophenylazo)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

文献信息

• Alkyl-sulfur versus aryl-sulfur bond cleavage in tridentate alkylthiophenylazonaphthols by group 9 metal ions
  作者：Suvra Acharya、Pinaki Bandyopadhyay、Purak Das、Sachidulal Biswas、Achintesh Narayan Biswas

  DOI：10.1016/j.jorganchem.2018.04.001

  日期：2018.7

  resulting complexes have been determined by single crystal X-ray crystallography. Rhodium(III) or iridium(III) binds desulfurized modified HL1-HL10 ligands via O, N, C(aryl) donor set. Cobalt(I), the remaining member of the group 9, regiospecifically cleaves the C(sp3)–S bond of the diazene ligands with concomitant two-electron oxidation leading to the formation of novel cobalt(III) complexes. The molecular

  具有C（sp 3）–S和芳基C（sp 2）–S键的单阴离子三齿烷基硫代苯基萘酚与低价的9族金属化合物的反应通过C（sp 2）–S或C（sp）提供单体金属络合物3）–S裂解。铑（I）和铱（I）选择性裂解2-羟基-1-（2'-烷基硫代苯基偶氮）萘（HL 1 -HL 5）和1-羟基-2-（2'的C（sp 2）–S键-烷基硫代苯基偶氮）萘（HL 6 -HL 10）伴随的基于双电子金属的氧化作用导致形成新型M（III）环金属盐。所得配合物的分子结构已通过单晶X射线晶体学测定。铑（III）或铱（III）通过O，N，C（芳基）供体对结合脱硫的修饰的HL 1 -HL 10配体。钴（I），第9组的剩余成员，通过区域特异性地裂解了重氮配体的C（sp 3）-S键，并伴随着两​​个电子的氧化，从而导致了新型钴（III）配合物的形成。所得钴（III）配合物之一的分子结构已通过单晶X射线晶体学测定。钴（III）中心结