1,4-naphthalenedione, mono[(2,4-dinitrophenyl)hydrazone] | 40881-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-naphthalenedione, mono[(2,4-dinitrophenyl)hydrazone]
• 英文别名: <1.4>Naphthochinon-mono-<2.4-dinitro-phenylhydrazon>；(4E)-4-[(2,4-dinitrophenyl)hydrazinylidene]naphthalen-1-one
• CAS: 40881-80-9
• 化学式: C₁₆H₁₀N₄O₅
• 分子量: 338.279
• InChiKey: UXPVTTSLZXVQGC-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127.74
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2,4-二硝基苯肼 、 1,4-萘醌 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 1,4-naphthalenedione, mono[(2,4-dinitrophenyl)hydrazone]
  参考文献：
  名称：

  Resonance Raman Observation of Surface Carbonyl Groups on Carbon Electrodes Following Dinitrophenylhydrazine Derivatization

  摘要：

  Dinitrophenylhydrazine (DNPH) was used to form hydrazone derivatives of carbonyl groups on glassy carbon (GC) and pyrolytic graphite surfaces. The DNPH adducts of benzoquinone and acetone have cross sections of 488 nm, much larger than those of either DNPH or the underivatized carbonyl group. The result of this enhancement is that the Raman spectrum of DNPH-modified GC is dominated by adduct features and is not sensitive to residual adsorbed reagents. In addition, resonance Raman active adducts were not formed from DNPH reactions with model compounds containing lactone, phenol, or carboxylate groups. Assuming that the cross section of surface carbonyl adducts on GC is comparable to that of the benzoquinone adduct, the detection limit for carbonyl groups on GC is less than 1% of a monolayer. The coverage of carbonyl groups increases significantly following electrochemical oxidation of both GC and highly ordered pyrolytic graphite. Analysis of the spectra of the benzoquinone/DNPH adduct permitted assignment of prominent resonance Raman and IR features and revealed that the electrons in the hydrazone linkage are delocalized extensively.

  DOI：

  10.1021/ac00101a026

文献信息

• Resonance Raman Observation of Surface Carbonyl Groups on Carbon Electrodes Following Dinitrophenylhydrazine Derivatization
  作者：Mark A. Fryling、Jun. Zhao、Richard L. McCreery

  DOI：10.1021/ac00101a026

  日期：1995.3.1

  Dinitrophenylhydrazine (DNPH) was used to form hydrazone derivatives of carbonyl groups on glassy carbon (GC) and pyrolytic graphite surfaces. The DNPH adducts of benzoquinone and acetone have cross sections of 488 nm, much larger than those of either DNPH or the underivatized carbonyl group. The result of this enhancement is that the Raman spectrum of DNPH-modified GC is dominated by adduct features and is not sensitive to residual adsorbed reagents. In addition, resonance Raman active adducts were not formed from DNPH reactions with model compounds containing lactone, phenol, or carboxylate groups. Assuming that the cross section of surface carbonyl adducts on GC is comparable to that of the benzoquinone adduct, the detection limit for carbonyl groups on GC is less than 1% of a monolayer. The coverage of carbonyl groups increases significantly following electrochemical oxidation of both GC and highly ordered pyrolytic graphite. Analysis of the spectra of the benzoquinone/DNPH adduct permitted assignment of prominent resonance Raman and IR features and revealed that the electrons in the hydrazone linkage are delocalized extensively.