1,4-Dioxo-1,2,3,4-tetrahydro-phthalazine-5-diazonium; chloride | 113443-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1,4-Dioxo-1,2,3,4-tetrahydro-phthalazine-5-diazonium; chloride
• 英文别名: 1,4-Dioxo-1,2,3,4-tetrahydrophthalazine-5-diazonium chloride；1,4-dioxo-2,3-dihydrophthalazine-5-diazonium;chloride
• CAS: 113443-78-0
• 化学式: C₈H₅N₄O₂*Cl
• 分子量: 224.606
• InChiKey: ZHLHAUBMNNDMNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-Dioxo-1,2,3,4-tetrahydro-phthalazine-5-diazonium; chloride 、 乙酰丙酮 在 sodium hydroxide 作用下， 生成 5-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)-2,3-dihydrophthalazine-1,4-dione
  参考文献：
  名称：

  New arylhydrazones of β-diketones and their optical and thermal properties

  摘要：

  New arylhydrazones of beta-diketones, 2-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl) benzoic acid (1) and (Z)-ethyl-2-(2-(2-nitrophenyl)hydrazono)-3-oxobutanoate (2), have been synthesized by reaction of activated beta-diketones with the corresponding aryldiazonium salts, and characterized by IR, H-1 and C-13 NMR spectroscopies and elemental analysis. In DMSO solution, 1 is stable exclusively in the hydrazone form, while 2 exists in DMSO and H2O solutions as a mixture of enol-azo and hydrazone tautomeric forms. In the latter case, an increase in the solvent polarity shifts the tautomeric balance to the enol-azo form. Solvatochromic, thermal and photoluminescent properties of 1,2 and the known related 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzoic acid (3), (2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)phenyl)arsonic acid (4), (Z)-2-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)benzoic acid (5) and 5-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)-2,3-dihydrophthalazine-1,4-dione (6) were studied. The obtained UV-vis absorption spectra confirm that epsilon(max) depends on the solvent and on the nature of AHBD, but no clear correlation was found. Upon heating, 1-3,5 and 6 are stable up to 474 K and decompose in two steps whereas 4 decomposes in three steps starting from 343 K. The kinetic parameters of the thermal decomposition were estimated suggesting a low rate of the thermal decomposition. Compounds 2 and 3 exhibit luminescence with intense emission bands with maxima at lambda(em) of 466.0 (lambda(ex) = 318 nm) and 532.5 nm (lambda(ex) = 315 nm), respectively, while compounds 4 and 6 show low-intensity bands at lambda(em) of 501 (lambda(ex) = 396 nm) and 503 nm (lambda(ex) = 389 nm). Compounds 1 and 5 display no photoluminescence. (C) Crown Copyright 2012 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.03.054

文献信息

• Thankarajan, N.; Krishnankutty, K.; Srinivasan, T. K. K., Journal of the Indian Chemical Society, <hi>1986</hi>, vol. 63, p. 977 - 979
  作者：Thankarajan, N.、Krishnankutty, K.、Srinivasan, T. K. K.

  DOI：——

  日期：——