1-Cyano-1-p-nitrophenyl-4-phenylbuta-1E,3E-diene

• 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: 1-Cyano-1-p-nitrophenyl-4-phenylbuta-1E,3E-diene
• 英文别名: 2-(p-nitrophenyl)-5-phenylpenta-2,4-dienenitrile；(2Z,4E)-2-(4-nitrophenyl)-5-phenylpenta-2,4-dienenitrile
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: QNCCJFFKMYHSBA-LHQXNBGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对硝基苯乙腈 、 肉桂醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以82%的产率得到1-Cyano-1-p-nitrophenyl-4-phenylbuta-1E,3E-diene
  参考文献：
  名称：

  Structural and computational studies of 2,5-diarylpenta-2,4-dienenitriles

  摘要：

  2,5-Diarylpenta-2,4-dienenitriles 1-9 were synthesized and characterized by the high resolution H-1, C-13, H-1-H-1 COSY and H-1-C-13 COSY spectra. Spectral data indicate the trans arrangement of the side chain protons H(3), H(4) and H(5) and trans orientation of H(3) proton with respect to cyano group in 1-9. Computational calculations were carried out for some possible structures and they support the conformation in which all side chain protons are trans to each other and H(3) proton is trans to CN group. Moreover, syn orientation of NO2 group with respect to H(5) proton in 4-6 is revealed by computational calculations and chemical shift data. From the favored conformations, geometrical parameters, HOMO-LUMO energies, dipole moment, polarizabilities and first order hyperpolarizabilities were determined theoretically. The highest beta(tot) is observed for the nitrile 9 where electron releasing substituent (OCH3) and electron withdrawing substituent (NO2) are present at the opposite ends of the conjugated system and hence it is the best NLO candidate. The NLO character decreases according to the order 9 > 3 > 5 > 4 > 7 > 8 > 6 > 2 > 1. The H-1 and C-13 chemical shifts in gaseous state as well as in solution were also determined theoretically by DFT method and they are in agreement with the experimental values. NBO analyses were further carried out for the minimum energy conformer. From H-1 and C-13 chemical shifts, the effect of introduction of substituents (NO2, OCH3, Cl) in the phenyl ring on the chemical shifts of the side chain protons [H(3), H(4) and H(5)] and carbons [C(3), C(4) and C(5)] were analyzed in detail. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.03.060

文献信息

• α,ω-Diphenylpolyenes Cabable of Exhibiting Twisted Intramolecular Charge Transfer Fluorescence: A Fluorescence and Fluorescence Probe Study of Nitro- and Nitrocyano-Substituted 1,4-Diphenylbutadienes
  作者：Anil K. Singh、Manjula Darshi、Sriram Kanvah

  DOI：10.1021/jp992275a

  日期：2000.1.1

  1,4-Diphenylbutadiene compounds, namely 1-p-cyanophenyl-4-phenylbuta-1E,3E-diene (2), 1-p-nitrophenyl-4-phenylbuta-1E,3E-diene (3), 1-cyano-1,4-diphenylbuta-1Z,3E-diene (4), 1-p-cyanophenyl-4-p-nitrophenylbuta-1E,3E-diene (5), 1-cyano-1-p-nitrophenyl-4-phenylbuta-1Z,3E-diene (6), and 1-cyano-1-phenyl-4-p-nitrophenylbuta-1Z,3E-diene (7), have been synthesized and their absorption and fluorescence properties in organic solvents, water-dioxane, and SDS, CTAB, and Triton-X-100 micelles have been investigated. The fluorescence behavior of these dienes has also been examined in ethanol-methanol (1:1) matrix at 298 and 77 K. The dienes with nitro substituents on the aromatic ring are capable of exhibiting dramatically redshifted fluorescence emission due to twisted intramolecular charge-transfer excited states. The fluorescence properties of nitro-substituted dienes 3, and 5-7 have been utilized to probe the microenvironment of SDS and CTAB micelles Ln terms of dielectric constant of water-micelle interface, location of the probe molecules in the micelles, and the cme values. This study has brought out interesting features of the excited state structure and potential energy surface of diphenylpolyenes. It further provides new directions for the development of fluorescence probes as sensors and reporters of microenvironments of organized assemblies.
• Structural and computational studies of 2,5-diarylpenta-2,4-dienenitriles
  作者：A. Manimekalai、A. Balamurugan

  DOI：10.1016/j.molstruc.2011.03.060

  日期：2011.5

  2,5-Diarylpenta-2,4-dienenitriles 1-9 were synthesized and characterized by the high resolution H-1, C-13, H-1-H-1 COSY and H-1-C-13 COSY spectra. Spectral data indicate the trans arrangement of the side chain protons H(3), H(4) and H(5) and trans orientation of H(3) proton with respect to cyano group in 1-9. Computational calculations were carried out for some possible structures and they support the conformation in which all side chain protons are trans to each other and H(3) proton is trans to CN group. Moreover, syn orientation of NO2 group with respect to H(5) proton in 4-6 is revealed by computational calculations and chemical shift data. From the favored conformations, geometrical parameters, HOMO-LUMO energies, dipole moment, polarizabilities and first order hyperpolarizabilities were determined theoretically. The highest beta(tot) is observed for the nitrile 9 where electron releasing substituent (OCH3) and electron withdrawing substituent (NO2) are present at the opposite ends of the conjugated system and hence it is the best NLO candidate. The NLO character decreases according to the order 9 > 3 > 5 > 4 > 7 > 8 > 6 > 2 > 1. The H-1 and C-13 chemical shifts in gaseous state as well as in solution were also determined theoretically by DFT method and they are in agreement with the experimental values. NBO analyses were further carried out for the minimum energy conformer. From H-1 and C-13 chemical shifts, the effect of introduction of substituents (NO2, OCH3, Cl) in the phenyl ring on the chemical shifts of the side chain protons [H(3), H(4) and H(5)] and carbons [C(3), C(4) and C(5)] were analyzed in detail. (C) 2011 Elsevier B.V. All rights reserved.