ethyl 4-[(3,5-dinitrobenzoyl)hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate | 1360181-33-4

• 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: ethyl 4-[(3,5-dinitrobenzoyl)hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 1360181-33-4
• 化学式: C₁₈H₁₉N₅O₇
• 分子量: 417.378
• InChiKey: UUOIAMJAKNJEES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  169.83
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  3-乙酰基-2,4-二甲基-5-乙氧羰基吡咯 、 3,5-二硝基苯甲酰肼 在 polyphosphoric acid 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以40.09%的产率得到ethyl 4-[(3,5-dinitrobenzoyl)hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis, molecular structure and spectral analysis of ethyl 4-[(3,5-dinitrobenzoyl)-hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate: A combined experimental and quantum chemical approach

  摘要：

  A new hydrazone, ethyl 4-[(3.5-dinitrobenzoyl)-hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate (PDNBAH) has been synthesized and characterized by FT-IR, H-1 NMR, UV-visible spectroscopy. All the quantum chemical calculations have been performed by density functional theory (OFT), using B3LYP functional and 6-31G(d,p) as basis set. The calculated and experimental wavenumber analyses confirm the existence of dimer of PDNBAH. The calculated binding energies of dimer using DFT and Bader's atoms in molecules (AIM) theory are -14.32 and -15.41 kcal/mol respectively. The intermolecular hydrogen bond energy of dimer due to the involvement of intermolecular hetero-nuclear double hydrogen bonds (N-H center dot center dot center dot O=C) through pyrrolic N-H and C=O of ester is also calculated to be equal to -12.29 kcal/mol using AIM calculation. The strength and the nature of hydrogen bonding and weak interactions in dimer have been analyzed by AIM theory in detail. The presence of resonance assisted hydrogen bonds (RAHB) has been confirmed by calculated ellipticity parameters using AIM calculation. The calculated thermodynamic parameters show that the reaction is non spontaneous at room temperature. The local reactivity descriptors show that C(13) is most reactive site for nucleophilic attack. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.11.057