4-chloro-benzaldehyde 4-p-tolyl-thiosemicarbazone | 97496-61-2

• 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: 4-chloro-benzaldehyde 4-p-tolyl-thiosemicarbazone
• 英文别名: 1-[(4-chlorophenyl)methylideneamino]-3-(4-methylphenyl)thiourea
• CAS: 97496-61-2
• 化学式: C₁₅H₁₄ClN₃S
• 分子量: 303.815
• InChiKey: LJMLWECHOWPSOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-benzaldehyde 4-p-tolyl-thiosemicarbazone 在 硫酸 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 [5-(4-Chloro-phenyl)-thiazolo[4,3-b][1,3,4]thiadiazol-2-yl]-p-tolyl-amine
  参考文献：
  名称：

  Singh; Yadav; Chaudhary, Journal of the Indian Chemical Society, 1983, vol. 60, # 8, p. 768 - 771

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲醛 、 4-4-甲苯基-3-胺基硫脲 以 乙醇 为溶剂， 生成 4-chloro-benzaldehyde 4-p-tolyl-thiosemicarbazone
  参考文献：
  名称：

  Singh; Yadav; Chaudhary, Journal of the Indian Chemical Society, 1983, vol. 60, # 8, p. 768 - 771

  摘要：

  DOI：

文献信息

• Synthesis of 2-amino-substituted-1,3,4-thiadiazoles via 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated intramolecular C–S bond formation in thiosemicarbazones
  作者：Sarangthem Joychandra Singh、Suresh Rajamanickam、Anupal Gogoi、Bhisma K. Patel

  DOI：10.1016/j.tetlet.2016.01.083

  日期：2016.3

  An effective oxidative intramolecular cyclization (C–S bond formation) of thiosemicarbazones using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has been developed to afford a diverse array of 2-amino-substituted-1,3,4-thiadiazoles. The attractive features of this protocol are operational simplicity, obviates the need of expensive transition-metal catalysts and broad substrate scope.

  已开发出使用2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）的硫半脲的有效氧化分子内环化（CS键形成），以提供各种2-氨基取代的- 1,3,4-噻二唑。该协议的吸引人的特点是操作简单，无需昂贵的过渡金属催化剂和广泛的底物范围。
• Srinivasan,V.R.; Ramachander,G., Indian Journal of Chemistry, 1963, vol. 1, p. 234 - 236
  作者：Srinivasan,V.R.、Ramachander,G.

  DOI：——

  日期：——
• Synthesis, spectroscopic and redox properties of some ruthenium(II) thiosemicarbazone complexes: Structural description of four of these complexes
  作者：Dipankar Mishra、Subhendu Naskar、Michael G.B. Drew、Shyamal Kumar Chattopadhyay

  DOI：10.1016/j.ica.2005.11.001

  日期：2006.1

  Sixteen neutral mixed ligand thiosemicarbazone complexes of ruthenium having general formula [Ru(PPh3)(2)L-2], where LH = 1-(arylidine)4-aryl thiosemicarbazones, have been synthesized and characterized. All complexes are diamagnetic and hence ruthenium is in the +2 oxidation state (low-spin d(6), S = 0). The complexes show several intense peaks in the visible region due to allowed metal to ligand charge transfer transitions. The structures of four of the complexes have been determined by single-crystal X-ray diffraction and they show that thiosemicarbazone ligands coordinate to the ruthenium center through the hydrazinic nitrogen and sulfur forming four-membered chelate rings with ruthenium in N2S2P2 coordination environment. In dichloromethane solution, the complexes show two quasi-reversible oxidative responses corresponding to loss of electron from HOMO and HOMO - 1. The E-0 values of the above two oxidations shows good linear relationship with Hammett substituents constant (sigma) as well as with the HOMO energy of the molecules calculated by the EHMO method. A DFT calculation on one representative complex suggests that there is appreciable contribution of the sulfur p-orbitals to the HOMO and HOMO - 1. Thus, assignment of the oxidation state of the metal in such complexes must be made with caution. (c) 2005 Elsevier B.V. All rights reserved.