2-(p-chlorophenyl)-5-(p-methoxyphenyl)penta-2,4-dienenitrile | 1313706-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(p-chlorophenyl)-5-(p-methoxyphenyl)penta-2,4-dienenitrile
• 英文别名: (2Z,4E)-2-(4-chlorophenyl)-5-(4-methoxyphenyl)penta-2,4-dienenitrile
• CAS: 1313706-56-7
• 化学式: C₁₈H₁₄ClNO
• 分子量: 295.768
• InChiKey: FETJJWJRLDRGDW-PCSFBJKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基肉桂醛 、 对氯苯乙腈 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以84%的产率得到2-(p-chlorophenyl)-5-(p-methoxyphenyl)penta-2,4-dienenitrile
  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

• 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.