3,4,5-trimethoxybenzaldehyde-4-nitrophenylhydrazone | 200933-50-2

• 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: 3,4,5-trimethoxybenzaldehyde-4-nitrophenylhydrazone
• 英文别名: 4-nitro-N-[(3,4,5-trimethoxyphenyl)methylideneamino]aniline
• CAS: 200933-50-2
• 化学式: C₁₆H₁₇N₃O₅
• 分子量: 331.328
• InChiKey: BKTYVPCKKUIMQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 4-硝基苯肼 在 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以72%的产率得到3,4,5-trimethoxybenzaldehyde-4-nitrophenylhydrazone
  参考文献：
  名称：

  4-Nitrophenylhydrazone Crystals with Large Quadratic Nonlinear Optical Response by Optimal Molecular Packing

  摘要：

  We investigate a novel nonlinear optical nitrophenylhydrazone (NPH) crystal, 3,4,5-trimethoxybenzaldehyde-4-nitrophenylhydrazone (TMO-NPH). Compared with many acentric NPH crystals having rod-shaped heads reported previously, the TMO-NPH molecule maintains the acentric intermolecular hydrogen bond synton through hydrazone and nitro groups but has distinct space filling characteristics due to a different shape of the headgroup, the disk-shaped trimethoxybenzaldehyde. We investigated the crystal structure and its characteristics, as well as details of the microscopic and the macroscopic nonlinear optical properties by quantum chemical calculations using density functional theory (DFT) and powder second-harmonic generation at nonresonant conditions. For comparison, DA-NPH (4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone) having a rod-shaped head and known nonlinear optical properties is also investigated by the same analysis. TMO-NPH crystals have the monoclinic space group symmetry Pn and exhibit a large macroscopic optical nonlinearity due to a favorable molecular packing with a very high order parameter cos(3) (theta(P)) = 0.90, while DA-NPH exhibits a lower order parameter cos(3)(theta(P)) = 0.33. The diagonal effective hyperpolarizability tensor component of TMO-NPH crystals is 30% higher than the largest tensor component of DA-NPH, even though the microscopic molecular susceptibility of TMO-NPH molecule is only about half of the one of DANPH.

  DOI：

  10.1021/cg200320f

文献信息

• 4-Nitrophenylhydrazone Crystals with Large Quadratic Nonlinear Optical Response by Optimal Molecular Packing
  作者：Eun-Young Choi、Pil-Joo Kim、Mojca Jazbinsek、Jong-Taek Kim、Yoon Sup Lee、Peter Günter、Soon W. Lee、O-Pil Kwon

  DOI：10.1021/cg200320f

  日期：2011.7.6

  We investigate a novel nonlinear optical nitrophenylhydrazone (NPH) crystal, 3,4,5-trimethoxybenzaldehyde-4-nitrophenylhydrazone (TMO-NPH). Compared with many acentric NPH crystals having rod-shaped heads reported previously, the TMO-NPH molecule maintains the acentric intermolecular hydrogen bond synton through hydrazone and nitro groups but has distinct space filling characteristics due to a different shape of the headgroup, the disk-shaped trimethoxybenzaldehyde. We investigated the crystal structure and its characteristics, as well as details of the microscopic and the macroscopic nonlinear optical properties by quantum chemical calculations using density functional theory (DFT) and powder second-harmonic generation at nonresonant conditions. For comparison, DA-NPH (4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone) having a rod-shaped head and known nonlinear optical properties is also investigated by the same analysis. TMO-NPH crystals have the monoclinic space group symmetry Pn and exhibit a large macroscopic optical nonlinearity due to a favorable molecular packing with a very high order parameter cos(3) (theta(P)) = 0.90, while DA-NPH exhibits a lower order parameter cos(3)(theta(P)) = 0.33. The diagonal effective hyperpolarizability tensor component of TMO-NPH crystals is 30% higher than the largest tensor component of DA-NPH, even though the microscopic molecular susceptibility of TMO-NPH molecule is only about half of the one of DANPH.