(E)-2-(2-(thiophen-2-ylmethylene)hydrazinyl)benzo[d]thiazole | 53846-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (E)-2-(2-(thiophen-2-ylmethylene)hydrazinyl)benzo[d]thiazole
• 英文别名: (E)-2-Benzothiazolylhydrazone 2-thiophenecarboxaldehyde；(2Z)-2-[(2E)-(thiophen-2-ylmethylidene)hydrazinylidene]-2,3-dihydro-1,3-benzothiazole；N-[(E)-thiophen-2-ylmethylideneamino]-1,3-benzothiazol-2-amine
• CAS: 53846-93-8
• 化学式: C₁₂H₉N₃S₂
• 分子量: 259.356
• InChiKey: YHGVHRFSRANAMU-MDWZMJQESA-N

物化性质

• 沸点：
  427.2±37.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(thiophen-2-ylmethylene)hydrazinyl)benzo[d]thiazole 、 溶剂黄146 、 lead(IV) acetate 以52%的产率得到
  参考文献：
  名称：

  DESHPANDE D. S., J. INDIAN CHEM. SOC., 1979, 56, NO 7, 742-743

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻吩甲醛 、 2-肼基苯并噻唑 以 乙醇 为溶剂， 以60%的产率得到(E)-2-(2-(thiophen-2-ylmethylene)hydrazinyl)benzo[d]thiazole
  参考文献：
  名称：

  Structures of hydrazones, (E)-2-(1,3-benzothiazolyl)-NHNCHAr, [Ar=4-(pyridin-2-yl)phenyl, pyrrol-2-yl, thien-2-yl and furan-2-yl]: Difference in conformations and intermolecular hydrogen bonding

  摘要：

  Structures of hydrazones, (E)-2-(1,3-benzothiazolyl)-NH-N=CH-Ar(Ar = pyridine-2-yl (1), pyrrol-2-yl (2), thien-2-yl (3) and furan-2-yl (4), prepared from 2-hydrazinyl-1,3-benzothiazole and ArCHO, followed by recrystallisation from alcohol solutions, are reported. No significant intramolecular hydrogen bonds are present in any of the four molecules. Different conformations were found between 2 and 3, on one hand and for 4, on the other. Thus for 4, the oxygen atom of the furanyl ring is on the same side of the molecule as is the sulfur atom of the benzothiazole unit, while in contrast, each of the heteroatoms of the thienyl and pyrrole rings lies on opposite sides to the benzothiazole sulphur atom. In addition to the conformational variations, differences are noted in the connections between molecules. Despite the presence in each case of N-(hydrazono)-H-N-(benzothiazolo) intermolecular hydrogen bonds, molecules of 4 are linked into spiral chains, while molecules of 2 and 3 (and indeed all compounds having Ar = substituted phenyl) form symmetric dimers. Further intermolecular interactions, albeit weaker ones, are found in 2 [C-H center dot center dot N and N-H center dot center dot pi], 3 [C-H center dot center dot pi] and 4 [pi center dot center dot pi] while dimers of 1 remain essentially free. Calculations carried out using the DFT(B3LYP)/6-311++G(d,p) method indicated that the conformations determined by crystallography for 2-4 were the more stable. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.09.058

文献信息

• MECHKOV, TS. D.;DEMIREVA, Z. I.;DAVARSKI, K. A., GOD. VISSH. XIM.-TEXNOL. IN-T. BURGAS, 1983, 18, N 2, 85-92
  作者：MECHKOV, TS. D.、DEMIREVA, Z. I.、DAVARSKI, K. A.

  DOI：——

  日期：——
• DESHPANDE D. S., CURR. SCI. (INDIA) <CUSC-AM>, 1977, 46, NO 4, 97-99
  作者：DESHPANDE D. S.

  DOI：——

  日期：——
• Structures of hydrazones, (E)-2-(1,3-benzothiazolyl)-NHNCHAr, [Ar=4-(pyridin-2-yl)phenyl, pyrrol-2-yl, thien-2-yl and furan-2-yl]: Difference in conformations and intermolecular hydrogen bonding
  作者：Eric B. Lindgren、Julliane D. Yoneda、Katia Z. Leal、Antônio F. Nogueira、Thatyana R.A. Vasconcelos、James L. Wardell、Solange M.S.V. Wardell

  DOI：10.1016/j.molstruc.2012.09.058

  日期：2013.3

  Structures of hydrazones, (E)-2-(1,3-benzothiazolyl)-NH-N=CH-Ar(Ar = pyridine-2-yl (1), pyrrol-2-yl (2), thien-2-yl (3) and furan-2-yl (4), prepared from 2-hydrazinyl-1,3-benzothiazole and ArCHO, followed by recrystallisation from alcohol solutions, are reported. No significant intramolecular hydrogen bonds are present in any of the four molecules. Different conformations were found between 2 and 3, on one hand and for 4, on the other. Thus for 4, the oxygen atom of the furanyl ring is on the same side of the molecule as is the sulfur atom of the benzothiazole unit, while in contrast, each of the heteroatoms of the thienyl and pyrrole rings lies on opposite sides to the benzothiazole sulphur atom. In addition to the conformational variations, differences are noted in the connections between molecules. Despite the presence in each case of N-(hydrazono)-H-N-(benzothiazolo) intermolecular hydrogen bonds, molecules of 4 are linked into spiral chains, while molecules of 2 and 3 (and indeed all compounds having Ar = substituted phenyl) form symmetric dimers. Further intermolecular interactions, albeit weaker ones, are found in 2 [C-H center dot center dot N and N-H center dot center dot pi], 3 [C-H center dot center dot pi] and 4 [pi center dot center dot pi] while dimers of 1 remain essentially free. Calculations carried out using the DFT(B3LYP)/6-311++G(d,p) method indicated that the conformations determined by crystallography for 2-4 were the more stable. (c) 2012 Elsevier B.V. All rights reserved.
• DESHPANDE D. S., J. INDIAN CHEM. SOC., 1979, 56, NO 7, 742-743
  作者：DESHPANDE D. S.

  DOI：——

  日期：——