(Z)-N'-(1-phenylethylidene)isonicotinic hydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (Z)-N'-(1-phenylethylidene)isonicotinic hydrazide
• 英文别名: Isonicotinic acid (1-phenyl-ethylidene)-hydrazide；N-[(Z)-1-phenylethylideneamino]pyridine-4-carboxamide
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: KBNUSICRUXGHRJ-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-N'-(1-phenylethylidene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 0.5h， 生成 isonicotinic acid-(1-phenyl-ethylidenehydrazide)
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  isonicotinic acid-(1-phenyl-ethylidenehydrazide) 以 乙腈 为溶剂， 反应 0.42h， 生成 (Z)-N'-(1-phenylethylidene)isonicotinic hydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519

文献信息

• Surface interaction and inhibition mechanisms of hydrazide derivatives on N80 steel in acidizing media: A comprehensive analysis through experimental and theoretical methods
  作者：Badr El-Haitout、Hassane Lgaz、Mustafa R. Al-Hadeethi、Han-Seung Lee、Raihana Jannat Adnin、Mouslim Messali、Khadija Haboubi、Lahcen Bazzi、Rachid Salghi

  DOI：10.1016/j.cplett.2023.140980

  日期：2024.1

  hydrazide derivatives, PEH and PAH, as corrosion inhibitors for N80 steel in acidic conditions. Utilizing a blend of experimental tests and theoretical calculations, including EIS, PDP, SEM, DFTB, and MD simulations, up to 96% inhibition efficiency was attained. Specifically, the PAH compound displayed notable protection. The Langmuir adsorption model confirmed dual adsorption, and theoretical simulations

  本研究评估了酰肼衍生物、PEH 和 PAH 作为 N80 钢在酸性条件下的缓蚀剂。综合利用实验测试和理论计算（包括 EIS、PDP、SEM、DFTB 和 MD 模拟），抑制效率高达 96%。具体而言，PAH 化合物显示出显着的保护作用。Langmuir 吸附模型证实了双重吸附，理论模拟揭示了相互作用机制。该研究为抑制剂分子和铁原子之间共价键的形成提供了宝贵的见解，并为开发适合工业应用的先进腐蚀抑制剂提供了一条有前途的道路。
• Arena; Capozza; Maccari, Revista Bras il eira de Farmaco gnosia, 1996, vol. 51, # 7, p. 517 - 523
  作者：Arena、Capozza、Maccari、Ottana、Vigorita

  DOI：——

  日期：——
• Acylhydrazones as Widely Tunable Photoswitches
  作者：Derk Jan van Dijken、Petr Kovaříček、Svante P. Ihrig、Stefan Hecht

  DOI：10.1021/jacs.5b09519

  日期：2015.12.2

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.