N,N-diethyl-3,5-dimethyl-4-nitroaniline | 723733-82-2

• 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: N,N-diethyl-3,5-dimethyl-4-nitroaniline
• CAS: 723733-82-2
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: FCEMIXSNSVYVSH-UHFFFAOYSA-N

物化性质

• 沸点：
  353.5±30.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-3,5-dimethyl-4-nitroaniline 在 盐酸 、 锌 作用下， 反应 1.0h， 生成 2,6-dimethyl-4-(diethylamino)aniline
  参考文献：
  名称：

  Experimental and theoretical study of near-infrared absorbing naphthoquinone methide dyes with a nonplanar geometry

  摘要：

  The bathochromic shift of the near-infrared absorption spectra of naphthoquinone methide dyes has been observed as a function of increased steric hindrance between the quinone imine and aniline segments. This novel shift that results from the loss of planarity has been examined by means of semiempirical INDO/S and AM1 models. Based on the configuration interaction (CI) analysis, the observed transitions in both the near-infrared and UV regions have been assigned. The introduction of an acetylamino group at the 2-position of aniline ring has caused a bathochromic shift with a remarkable increase in molecular extinction coefficient. In order to interpret these results, both an electronic factor and a steric effect have been analyzed. This interesting color-structure relationship of a nonplanar chromophoric system has been elucidated.

  DOI：

  10.1021/ja00008a012
• 作为产物：
  描述：

  3,5-dimethyl-N,N-diethylaniline 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 N,N-diethyl-3,5-dimethyl-4-nitroaniline
  参考文献：
  名称：

  Experimental and theoretical study of near-infrared absorbing naphthoquinone methide dyes with a nonplanar geometry

  摘要：

  The bathochromic shift of the near-infrared absorption spectra of naphthoquinone methide dyes has been observed as a function of increased steric hindrance between the quinone imine and aniline segments. This novel shift that results from the loss of planarity has been examined by means of semiempirical INDO/S and AM1 models. Based on the configuration interaction (CI) analysis, the observed transitions in both the near-infrared and UV regions have been assigned. The introduction of an acetylamino group at the 2-position of aniline ring has caused a bathochromic shift with a remarkable increase in molecular extinction coefficient. In order to interpret these results, both an electronic factor and a steric effect have been analyzed. This interesting color-structure relationship of a nonplanar chromophoric system has been elucidated.

  DOI：

  10.1021/ja00008a012

文献信息

• Experimental and theoretical study of near-infrared absorbing naphthoquinone methide dyes with a nonplanar geometry
  作者：Yuji Kubo、Katsuhira Yoshida、Masafumi Adachi、Shinichiro Nakamura、Shuichi Maeda

  DOI：10.1021/ja00008a012

  日期：1991.4

  The bathochromic shift of the near-infrared absorption spectra of naphthoquinone methide dyes has been observed as a function of increased steric hindrance between the quinone imine and aniline segments. This novel shift that results from the loss of planarity has been examined by means of semiempirical INDO/S and AM1 models. Based on the configuration interaction (CI) analysis, the observed transitions in both the near-infrared and UV regions have been assigned. The introduction of an acetylamino group at the 2-position of aniline ring has caused a bathochromic shift with a remarkable increase in molecular extinction coefficient. In order to interpret these results, both an electronic factor and a steric effect have been analyzed. This interesting color-structure relationship of a nonplanar chromophoric system has been elucidated.