κ2-N,N'-di-2-pyridyl ketone thiophene-2-carboxylic acid hydrazone | 141315-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: κ2-N,N'-di-2-pyridyl ketone thiophene-2-carboxylic acid hydrazone
• 英文别名: N'-(bis(2-pyridyl)methylidene)-thiophen-2-carboxylic acidhydrazide；di-2-pyridyl ketone thiophene-2-carboxylic acid hydrazone；di-2-pyridylketonethiophene-2-carboxylic acid hydrazone；di-2-pyridylketone 2-thiophenecarboxaldehyde hydrazone；1-(2-thenoyl)-2-(2,2'-dipyridyl methylene)hydrazine；di-2-pyridylketone 2-thenoylhydrazone；N-[bis(2-pyridyl)methyleneamino]thiophene-2-carboxamide；N-(dipyridin-2-ylmethylideneamino)thiophene-2-carboxamide
• CAS: 141315-41-5
• 化学式: C₁₆H₁₂N₄OS
• 分子量: 308.363
• InChiKey: BZIUUPPTELHLQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五羰基溴化锰(I) 、 κ2-N,N'-di-2-pyridyl ketone thiophene-2-carboxylic acid hydrazone 以 乙醚 为溶剂， 以68%的产率得到fac-[Mn(CO)3(η2-N,N di-2-pyridyl ketone thiophene-2-carboxylic acid hydrazone)Br]
  参考文献：
  名称：

  二-2-吡啶基酮噻吩-2-羧酸腙 (dpktch) 锰化合物的合成、光谱和 X 射线晶体学分析：Mn(CO)5Br 与 dpktch 的反应

  摘要：

  摘要 [Mn(CO)5Br]、二-2-吡啶基酮噻吩-2-甲腙(dpktch)和乙醚的混合物在空气中超声辐射得到fac-[Mn(CO)3(η2-N ,N-dpktch)Br]。在回流条件下 [MnBr2(η3-N,N,O-dpktch)] 和 [Mn(η3-N,N,O-dpktch-H)2] 从 Mn(CO)5Br、dpktch 和CH3CN。分离化合物的红外光谱揭示了 fac-[Mn(CO)3(η2-N,N-dpktch)Br] 中羰基 (CO) 基团的面配位，[ MnBr2(η3-N,N,O-dpktch)]和[Mn(η3-N,N,O-dpktch-H)2]，以及dpktch/dpktch-H的配位。分离出的化合物的电子吸收光谱显示出两个配体内电荷转移 (ILCT) 跃迁，它们对其周围环境的变化很敏感。fac-[Mn(CO)3(η2-N, N-dpktch)Br] 及其共轭碱 fac-[Mn(CO)3(η2-N

  DOI：

  10.1016/j.molstruc.2010.01.005
• 作为产物：
  描述：

  2-噻吩甲酰肼 、 2-二吡啶基酮 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 κ2-N,N'-di-2-pyridyl ketone thiophene-2-carboxylic acid hydrazone
  参考文献：
  名称：

  di-2-pyridylketone-2-thenoylhydrazone (dpktah) 在非水介质中的分子传感行为

  摘要：

  摘要 在二甲基亚砜 (dmso) 和 N , N - 二甲基甲酰胺 (dmf) 介质中对二-2-吡啶基酮-2-thenoylhydrazone (dpktah) 进行的光学测量揭示了两种对其环境变化敏感的配体内电荷转移 (ILCT) 跃迁。dpktah 化学环境的变化证明了两种构象之间的可逆互变（α-dpktah 与在 400 nm 处观察到的低能电子跃迁相关，β-dpktah 与在 326 nm 处观察到的电子跃迁相关），并允许计算它们的消光系数。热光测量证实了 α-dpktah 和 β-dpktah 之间的可逆互变，并给出 Δ H o = -39.57, -36.58 kJ mol -1 , Δ S o = -145.37, +108.57 J mol -1 , Δ G o = +3.77, +4.22 kJ mol -1 和 K = +0.22, +0.38 在 dmf 和 dmso

  DOI：

  10.1016/j.molstruc.2006.09.014

文献信息

• Spectroscopic and electrochemical properties of group 12 acetates of di-2-pyridylketone thiophene-2-carboxylic acid hydrazone (dpktch-H) complexes. The structure of [Cd(η3-N,N,O-dpktch-H)2]
  作者：Mohammed Bakir、Mark A.W. Lawrence、Shameal McBean

  DOI：10.1016/j.saa.2015.03.079

  日期：2015.7

  O-dpktch-H)]·nH2O and it conjugate acid [M(η(2)-O,O-OAc)(η(3)-N,N,O-dpktch)]·nH2O pointing to ligand exchange between the acetate and benzoate anions. When CH2Cl2 solutions of [M(η(2)-O,O-OAc)(η(3)-N,N,O-dpktch-H)]·nH2O were titrated with dmso, changes appeared pointing to solvolysis or ligand exchange reactions. Electrochemical measurements on dmso solutions of [M(η(2)-O,O-OAc)(η(3)-N,N,O-dpktch-H)]·nH2O

  [dpktch]与[M（OAc）2]（M =第12组金属原子）在回流的CH3CN中反应，得到[M（η（2）-O，O-OAc）（η（3）-N，N， O-dpktch-H）]·nH2O（n = 0或1）。红外和（1）H NMR光谱与[η（2）-O，O-OAc]和[η（3）-N，N，O-dpktch-H]（-）的配位相一致配方。在非水溶剂中测得的[M（η（2）-O，O-OAc）（η（3）-N，N，O-dpktch-H）]·nH2O的电子吸收光谱显示由于dpk的π-π∗导致配体电荷转移（ILCT）过渡，随后是dpk→噻吩电荷转移。[M（η（2）-O，O-OAc）（η（3）-N，N，O-dpktch-H）]·nH2O的电子跃迁取决于溶剂和浓度。用苯甲酸分光光度滴定[M（η（2）-O，O-OAc）（η（3）-N，N，O-dpktch-H）]·nH2O的dmso溶液显示[M之间不可逆的相互转化（η（2）
• Synthesis, characterization and structure of the first rhenium compound of di-2-pyridyl ketone thiophene-2-carboxylic acid hydrazone (dpktah), fac-[Re(CO)3(N,N-κ2-dpktah)Cl]
  作者：Mohammed Bakir、Colin Gyles

  DOI：10.1016/j.molstruc.2008.07.026

  日期：2009.1

  fac-[Re(CO)3(κ2-N,N-dpktah)Cl] confirmed its identity and divulge two symmetry-independent molecules in the asymmetric unit. The supramolecular structure of fac-[Re(CO)3(κ2-N,N-dpktah)Cl] disclosed anti-parallel chains locked via a network of hydrogen bonds. Non-classic hydrogen bonds of the type C–H…Cl connect molecules in the chain and classic hydrogen bonds of the type N–H…O connect adjacent chains.

  摘要 fac-[Re(CO)3(κ2-N,N -dpktah)Cl]，从 [Re(CO)5Cl] 和二-2-吡啶基酮噻吩-2-羧酸腙 (dpktah) 之间的反应中分离出来在回流的甲苯中，表现出丰富的理化性质。fac-[Re(CO)3(κ2-N,N-dpktah)Cl]的配方是根据其元素分析和光谱测量的结果确定的，并使用 X 射线晶体学进行确认。fac-[Re(CO)3(κ2-N,N-dpktah)Cl]的 1H NMR 谱揭示了 dpktah 的配位和酰胺质子的交换。电子吸收测量显示两个配体内电荷转移跃迁 (ILCT) 以及 fac-[Re(CO)3(κ2-N,N-dpktah)Cl] 与其共轭碱之间建立的相互转化。热光学研究证实了 fac-[Re(CO)3(κ2-N,N-dpktah)Cl] 与其共轭碱之间容易相互转化。光敏测量显示 [MCl2]（M = Zn、Cd 或 Hg）的浓度低至
• The different behaviour of the di-2-pyridylketone 2-thenoylhydrazone in two organotin compounds. Synthesis, X-ray structure and biological activity
  作者：Mauro Carcelli、Corrado Pelizzi、Giancarlo Pelizzi、Piergiorgio Mazza、Franca Zani

  DOI：10.1016/0022-328x(94)00003-u

  日期：1995.2

  Two organotin compounds [SnPh(dpt)Cl-2] (1) and [SnPh(3)Cl(OH2)].Hdpt (2) (Hdpt = di-2-pyridylketone 2-thenoylhydrazone) have been synthesized and characterized by IR spectroscopy and X-ray diffraction. Hdpt behaves differently in the two compounds: it is deprotonated and ONN tridentate in 1 and uncoordinated in 2, where pairs of hydrogen-bonded [SnPh(3)Cl(OH2)] and Hdpt molecules are present. The tin environment is octahedral in 1 and trigonal bipyramidal in 2. Compound 2 has shown good antimicrobial activity against Gram-positive bacteria and moulds in vitro. Neither compound showed genotoxic properties.
• Christidis, P. C.; Tossidis, I. A.; Hondroudis, C. A., Zeitschrift fur Kristallographie
  作者：Christidis, P. C.、Tossidis, I. A.、Hondroudis, C. A.

  DOI：——

  日期：——
• X-ray crystallographic, spectroscopic, and electrochemical properties of [HgCl2 (κ2-N,N′-dpktch)] (κ2-N,N′-dpktch=di-2-pyridyl ketone thiophene-2-carboxylic acid hydrazone)
  作者：Mohammed Bakir、Rebecca R. Conry、Orville Green

  DOI：10.1016/j.molstruc.2008.12.018

  日期：2009.3

  When dpktch was allowed to react with HgCl2 in acetonitrile under reflux, [HgCl2(kappa(2)-N,N '-dpktch)] was isolated in good yield. Infrared spectra disclosed the absence of Hg-O coordination and H-1 NMR Studies in d(6)-dmso revealed that [HgCl2(kappa(2)-N,N'-dpktch)] is sensitive to its environment and that its amide proton is exchangeable. Electronic absorption spectral measurements confirmed the sensitivity of [HgCl2(kappa(2)-N,N'-dpktch)] to changes ill its Surroundings. In an aprotic solvent Such as CH2Cl2, a single intra-ligand-charge-transfer transition (ILCT) due to [HgCl2(kappa(2)-N,N'-dpktch)] appeared, and in a protophilic solvent, two intra-ligand-charge-transfer transitions appeared due to [HgCl2(kappa(2)-N,N'-dpktch)] and its conjugate base. Electrochemical Measurements in dmf show electrochemical decomposition following redox processes, and highlight metal and ligand based redox properties due to HgCl2, and dpktch, X-ray crystallographic Studies On a triclinic, P (1) over bar single crystal of [HgCl2(kappa(2)-N,N'-dpktch)] show the N,N'-coordination of dpktch and the extended structure revealed polymeric stacks of anti-parallel sheets of [HgCl2(kappa(2)-N,N'-dpktch)] stabilized by a web of non-covalent bonds that include pi-pi stacking, hydrogen bonds, and short non-hydrogen intermolecular interactions. (c) 2008 Elsevier B.V. All rights reserved.