4-(1-formylnaphthalen-2-yloxy)phthalonitrile | 1402607-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1-formylnaphthalen-2-yloxy)phthalonitrile
• 英文别名: 4-(1-Formylnaphthalen-2-yl)oxybenzene-1,2-dicarbonitrile；4-(1-formylnaphthalen-2-yl)oxybenzene-1,2-dicarbonitrile
• CAS: 1402607-31-1
• 化学式: C₁₉H₁₀N₂O₂
• 分子量: 298.301
• InChiKey: IEKDNZFWZBHQKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 2-羟基-1-萘甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以19.86%的产率得到4-(1-formylnaphthalen-2-yloxy)phthalonitrile
  参考文献：
  名称：

  Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile

  摘要：

  The novel compound 4-(1-formylnaphthalen-2-yloxy)phthalonitrile, C19H10N2O2, has been synthesized and characterized by IR, UV-vis, NMR and X-ray single-crystal determination. The title compound, is built up from two planar groups (naphthalen and phthalonitrile), with a dihedral angle of 64.10(4)degrees between them. The crystal structure is stabilized by weak C-H center dot center dot center dot O hydrogen-bond and pi-pi interactions. The structural and spectroscopic data of the compound in the ground state have been calculated using density functional theory (DFT) and Hartree-Fock (HF) with the 6-31G(d,p) basis set. The vibrational study was interpreted in terms of potential energy distribution (PED). The observed wave number in FT-IR spectra was analyzed and assigned to different normal modes of the molecule. Using the TD-DFT and TD-HF methods, electronic absorption spectra of the title compound were predicted and good agreement with the TD-DFT method and the experimental determination was found. Isotropic chemical shifts (C-13 and H-1 NMR) were calculated using the gauge-invariant atomic orbital (GIAO) method. The HOMO and LUMO analyses were used to elucidate information regarding charge transfer within the molecule. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.07.005

文献信息

• Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile
  作者：Hidayet Tereci、İskender Askeroğlu、Nesuhi Akdemir、İbrahim Uçar、Orhan Büyükgüngör

  DOI：10.1016/j.saa.2012.07.005

  日期：2012.10

  The novel compound 4-(1-formylnaphthalen-2-yloxy)phthalonitrile, C19H10N2O2, has been synthesized and characterized by IR, UV-vis, NMR and X-ray single-crystal determination. The title compound, is built up from two planar groups (naphthalen and phthalonitrile), with a dihedral angle of 64.10(4)degrees between them. The crystal structure is stabilized by weak C-H center dot center dot center dot O hydrogen-bond and pi-pi interactions. The structural and spectroscopic data of the compound in the ground state have been calculated using density functional theory (DFT) and Hartree-Fock (HF) with the 6-31G(d,p) basis set. The vibrational study was interpreted in terms of potential energy distribution (PED). The observed wave number in FT-IR spectra was analyzed and assigned to different normal modes of the molecule. Using the TD-DFT and TD-HF methods, electronic absorption spectra of the title compound were predicted and good agreement with the TD-DFT method and the experimental determination was found. Isotropic chemical shifts (C-13 and H-1 NMR) were calculated using the gauge-invariant atomic orbital (GIAO) method. The HOMO and LUMO analyses were used to elucidate information regarding charge transfer within the molecule. (c) 2012 Elsevier B.V. All rights reserved.