1-(1H-pyrrol-2-yl)-pent-1-en-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(1H-pyrrol-2-yl)-pent-1-en-3-one
• 英文别名: 1-(1H-pyrrol-2-yl)pent-1-en-3-one
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: ABMGJRLTLOPEPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-吡咯甲醛 、 丁酮 在 potassium hydroxide 作用下， 以 水 为溶剂， 以88.56%的产率得到1-(1H-pyrrol-2-yl)-pent-1-en-3-one
  参考文献：
  名称：

  Antimicrobial activity, structural evaluation and vibrational (FT-IR and FT-Raman) study of pyrrole containing vinyl derivatives

  摘要：

  In this paper we present structural and vibrational study of three vinylpyrrole derivatives: 2-Cyano-3-(1H-pyrrol-2-yl)-acrylamide (CPA), 1-(1H-Pyrrol-2-yl)-Pent-1-en-3-one (PP) and 1-(1H-Pyrrol-2-yl)-but-1-en-3-one (PB), using ab initio, DFT and experimental approaches. The quantum chemical calculation have been performed on B3LYP method and 6-311 + G(d,p) basis set. The experimental FT-IR and Raman wavenumbers were compared with the respective theoretical values obtained from OFF calculations and found to agree well. The experimental FT-IR and Raman study clearly indicate that the compound exist as dimer in solid state. The binding energies of (CPA), (PP) and (PB) dimers are found to be 20.95, 18.75 and 19.18 kcal/mol, respectively. The vibrational analysis shows red shifts in v(N-H) and v(C=O) stretching as result of dimer formation. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using NBO analysis. Topological and energetic parameters reveal the nature of interactions in dimer. The local electronic descriptors analyses were used to predict the reactive sites in the molecule. Calculated first static hyperpolarizability of CPA, PP and PB is found to be 10.41 x 10(-3), 18.93 x 10(-30,) 18.29 x 10(-30) esu, respectively, shows that investigated molecules will have non-linear optical response and might be used as non-linear optical (NLO) material. These vinylpyrrole compounds (CPA), (PP) and (PB) showed antifungal and antibacterial activity against Aspergillus niger and gram-positive bacteria Bacillus subtili. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2015.09.032

文献信息

• Antimicrobial activity, structural evaluation and vibrational (FT-IR and FT-Raman) study of pyrrole containing vinyl derivatives
  作者：R.N. Singh、Poonam Rawat、Sangeeta Sahu、Yashvinder Kumar

  DOI：10.1016/j.saa.2015.09.032

  日期：2016.2

  In this paper we present structural and vibrational study of three vinylpyrrole derivatives: 2-Cyano-3-(1H-pyrrol-2-yl)-acrylamide (CPA), 1-(1H-Pyrrol-2-yl)-Pent-1-en-3-one (PP) and 1-(1H-Pyrrol-2-yl)-but-1-en-3-one (PB), using ab initio, DFT and experimental approaches. The quantum chemical calculation have been performed on B3LYP method and 6-311 + G(d,p) basis set. The experimental FT-IR and Raman wavenumbers were compared with the respective theoretical values obtained from OFF calculations and found to agree well. The experimental FT-IR and Raman study clearly indicate that the compound exist as dimer in solid state. The binding energies of (CPA), (PP) and (PB) dimers are found to be 20.95, 18.75 and 19.18 kcal/mol, respectively. The vibrational analysis shows red shifts in v(N-H) and v(C=O) stretching as result of dimer formation. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using NBO analysis. Topological and energetic parameters reveal the nature of interactions in dimer. The local electronic descriptors analyses were used to predict the reactive sites in the molecule. Calculated first static hyperpolarizability of CPA, PP and PB is found to be 10.41 x 10(-3), 18.93 x 10(-30,) 18.29 x 10(-30) esu, respectively, shows that investigated molecules will have non-linear optical response and might be used as non-linear optical (NLO) material. These vinylpyrrole compounds (CPA), (PP) and (PB) showed antifungal and antibacterial activity against Aspergillus niger and gram-positive bacteria Bacillus subtili. (C) 2015 Elsevier B.V. All rights reserved.