2-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)benzoic acid | 85090-56-8

• 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: 2-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)benzoic acid
• 英文别名: 2-[2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl]benzoic acid
• CAS: 85090-56-8
• 化学式: C₁₇H₁₄N₂O₄
• 分子量: 310.309
• InChiKey: MBPJXKPQBWNPMY-UHFFFAOYSA-N

物化性质

• 沸点：
  501.1±52.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  三氢化镧 、 2-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)benzoic acid 在 水 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  La(III) 配合物与苯甲酰丙酮和二苯甲酰甲烷的一些芳基腙的稳定性常数、结构和热重分析

  摘要：

  摘要 La(III) 与一些苄基丙酮 (BAAH) 和二苯甲酰甲烷 (DBMAH) 的芳基腙的连续稳定性常数已在 Bjerrum pH 计量滴定后通过电位测定法确定。金属螯合物的稳定性常数与哈米特取代基常数 (σ x ) 和分子结构相关。基于元素分析、红外光谱、核磁共振光谱和热重分析 (TG) 确定了配合物的结构。发现除了 OH - 基团之外，还通过 -NH 和 β-二酮的一个羰基发生螯合。配位数范围从 6 到 8，这是通过热重分析确认的。建议结构式。

  DOI：

  10.1016/0040-6031(89)85267-0
• 作为产物：
  描述：

  2-carboxybenzene diazonium chloride 、 1-苯基-1,3-丁二酮 在 sodium hydroxide 作用下， 生成 2-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)benzoic acid
  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

• New arylhydrazones of β-diketones and their optical and thermal properties
  作者：Zhen Ma、Abel M. Maharramov、Ismayil A. Aliyev、Irada N. Aliyeva、Maximilian N. Kopylovich、Gunel I. Amanullayeva、Kamran T. Mahmudov、Armando J.L. Pombeiro

  DOI：10.1016/j.molstruc.2012.03.054

  日期：2012.7

  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.
• Stability constants, structure and thermogravimetric analysis of La(III) complexes with some arylhydrazones of benzoylacetone and dibenzoylmethane
  作者：M.M. Khater、Y.M. Issa、A.L. El-Ansary、H.A. Mohamed

  DOI：10.1016/0040-6031(89)85267-0

  日期：1989.9

  Abstract The successive stability constants of La(III) with some arylhydrazones of benzylacetone (BAAH) and dibenzoylmethane (DBMAH) have been determined potentiometrically following the Bjerrum pH-metric titration. The stability constants of the metal chelates are correlated to the Hammett substituent constant (σ x ) and to the molecular structure. The structures of the complexes have been assigned on

  摘要 La(III) 与一些苄基丙酮 (BAAH) 和二苯甲酰甲烷 (DBMAH) 的芳基腙的连续稳定性常数已在 Bjerrum pH 计量滴定后通过电位测定法确定。金属螯合物的稳定性常数与哈米特取代基常数 (σ x ) 和分子结构相关。基于元素分析、红外光谱、核磁共振光谱和热重分析 (TG) 确定了配合物的结构。发现除了 OH - 基团之外，还通过 -NH 和 β-二酮的一个羰基发生螯合。配位数范围从 6 到 8，这是通过热重分析确认的。建议结构式。