4-fluoro-3-phenoxybenzoic acid hydrazide | 791615-40-2

• 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: 4-fluoro-3-phenoxybenzoic acid hydrazide
• 英文别名: 4-fluoro-3-phenoxybenzohydrazide；4-Fluoro-3-phenoxybenzohydrazide
• CAS: 791615-40-2
• 化学式: C₁₃H₁₁FN₂O₂
• 分子量: 246.241
• InChiKey: PPCCUPKKOUPLKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 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：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-fluoro-3-phenoxybenzoic acid hydrazide 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 5-(4-fluoro-3-phenoxyphenyl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Analysis of intermolecular interactions in 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol

  摘要：

  本研究通过单晶 X 射线衍射法制备了一种 1,2,4-三唑衍生物，即 3-(4-氟-3-苯氧基苯基)-1-((4-甲基哌嗪-1-基)甲基)-1H-1,2,4-三唑-5-硫醇 (T-1)，并对其进行了结构表征。通过观察发现，结晶固体中存在各种分子间相互作用，如 O-H ⋯S、C-H ⋯F、C-H ⋯S、C-H ⋯N、C-H ⋯O、C-H ⋯π、lp⋯π和π⋯π分子间相互作用，从而稳定了晶体结构。通过 PIXEL 方法评估了这些相互作用的能量，并将总能量分解为库仑能、极化能、色散能和斥力能。对硫的 H 键性质的研究表明，极化作用所产生的稳定作用非常重要。值得注意的是，据观察，晶体结构中溶剂分子的存在为原本不稳定的分子对（由不对称单元中的两个 1,2,4-三唑分子组成）提供了稳定性。

  DOI：

  10.1007/s12039-014-0700-2
• 作为产物：
  描述：

  4-氟-3-苯氧基苯甲酸 在 硫酸 、 一水合肼 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 4-fluoro-3-phenoxybenzoic acid hydrazide
  参考文献：
  名称：

  Mohan; Vishalakshi; Bhat, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 8, p. 1798 - 1801

  摘要：

  DOI：

文献信息

• Quantitative crystal structure analysis of 1,3,4-thiadiazole derivatives
  作者：Piyush Panini、T. P. Mohan、Usma Gangwar、Ravish Sankolli、Deepak Chopra

  DOI：10.1039/c3ce40278a

  日期：——

  A series of four biologically active 2-benzamido-5-(4-fluoro-3-phenoxyphenyl)-1,3,4-thiadiazoles derivatives have been synthesized and their crystal structures have been studied with systematic variations in the functional group at the para position of the benzamido ring. The molecular geometry of all these compounds is found to be L-shaped and their molecular conformation is found to be stabilized via S⋯O and F⋯C (lp⋯π) contacts. The lattice energies of these crystal structures have been calculated by PIXEL. Detailed quantitative analysis of the crystal packing have been performed with calculation of the interaction energies of the extracted molecular pairs from the crystal packing using PIXEL and these are further supported with inputs from high level DFT + Disp quantum mechanical calculations. The isostructurality present in the crystal packing has been investigated using XPAC. The Hirshfeld surfaces and consequently the fingerprint analysis have been performed to study the nature of interactions and their quantitative contributions towards the crystal packing. The electrostatic potential has been mapped over the Hirshfeld surface to explore the electrostatic complementarity which exists in the crystal packing. It is found that the weak interactions, such as C–H⋯OC/O–C, C–H⋯π, C–H⋯F, lp⋯π, π⋯π are significant contributors in the stabilization of the crystal packing in addition to the presence of strong N–H⋯N hydrogen bonds. It was observed that they are not only responsible for the alteration in the crystal structures, but their presence does provide extra stabilization in the absence of any structural change.

  我们合成了一系列具有生物活性的 2-苯甲酰胺基-5-(4-氟-3-苯氧基苯基)-1,3,4-噻二唑衍生物，并通过系统地改变苯甲酰胺环对位的官能团对它们的晶体结构进行了研究。研究发现，所有这些化合物的分子几何形状都呈 L 形，其分子构象通过 S⋯O 和 F⋯C (lp⋯π) 接触而稳定。这些晶体结构的晶格能是通过 PIXEL 计算得出的。通过使用 PIXEL 计算从晶体堆积中提取的分子对的相互作用能，对晶体堆积进行了详细的定量分析。使用 XPAC 对晶体堆积中存在的等结构性进行了研究。为了研究相互作用的性质及其对晶体堆积的定量贡献，还进行了 Hirshfeld 表面和指纹分析。在 Hirshfeld 表面上绘制了静电位图，以探索晶体堆积中存在的静电互补性。研究发现，除了存在强 N-H⋯N 氢键之外，C-H⋯OC/O-C、C-H⋯π、C-H⋯F、lp⋯π、π⋯π 等弱相互作用也是稳定晶体堆积的重要因素。据观察，它们不仅是改变晶体结构的原因，而且它们的存在确实在没有任何结构变化的情况下提供了额外的稳定性。
• Analysis of intermolecular interactions in 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol
  作者：PIYUSH PANINI、RAHUL SHUKLA、T P MOHAN、B VISHALAKSHI、DEEPAK CHOPRA

  DOI：10.1007/s12039-014-0700-2

  日期：2014.9

  In the present study, we have prepared and structurally characterized a derivative of 1,2,4 triazoles, namely 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol (T-1) via single crystal X-ray diffraction. The crystal structure was observed to be stabilized by the presence of various intermolecular interactions in the crystalline solid such as O-H ⋯S, C-H ⋯F, C-H ⋯S, C-H ⋯N, C-H ⋯O, C-H ⋯π, lp⋯π and π⋯π intermolecular interactions. The interaction energy of these interactions was evaluated through PIXEL method with decomposition of the total energy into the coulombic, polarization, dispersion and repulsion contribution. The study of the nature of H-bonds with sulfur reveals that stabilization due to contribution from polarization plays a significant role. It is noteworthy that the presence of the solvent molecules in the crystal structure were observed to provide stabilization to an otherwise destabilized molecular pair (comprising of two molecules of 1,2,4 triazoles in the asymmetric unit).

  本研究通过单晶 X 射线衍射法制备了一种 1,2,4-三唑衍生物，即 3-(4-氟-3-苯氧基苯基)-1-((4-甲基哌嗪-1-基)甲基)-1H-1,2,4-三唑-5-硫醇 (T-1)，并对其进行了结构表征。通过观察发现，结晶固体中存在各种分子间相互作用，如 O-H ⋯S、C-H ⋯F、C-H ⋯S、C-H ⋯N、C-H ⋯O、C-H ⋯π、lp⋯π和π⋯π分子间相互作用，从而稳定了晶体结构。通过 PIXEL 方法评估了这些相互作用的能量，并将总能量分解为库仑能、极化能、色散能和斥力能。对硫的 H 键性质的研究表明，极化作用所产生的稳定作用非常重要。值得注意的是，据观察，晶体结构中溶剂分子的存在为原本不稳定的分子对（由不对称单元中的两个 1,2,4-三唑分子组成）提供了稳定性。
• Quantitative analysis of intermolecular interactions in crystalline substituted triazoles
  作者：Dhananjay Dey、Saikat Kumar Seth、T.P. Mohan、Deepak Chopra

  DOI：10.1016/j.molstruc.2022.134380

  日期：2023.2

  using Hirshfeld surface and fingerprint analysis, PIXEL energy for molecular pairs, lattice energies for crystal packing, atoms-in-molecules (AIM) topological analysis, and noncovalent interaction (NCI) plots for intermolecular interactions. The fingerprint plots of the Hirshfeld surface analysis provide a quantitative picture of various substituent effects on the noncovalent interactions that contribute

  本手稿使用 Hirshfeld 表面和指纹分析、分子对的像素能量、晶体堆积的晶格能量、分子中原子 (AIM) 拓扑分析和分子间相互作用的非共价相互作用 (NCI) 图，全面检查了四种三唑衍生物。Hirshfeld 表面分析的指纹图提供了各种取代基对有助于这四种结构的晶体堆积稳定化的非共价相互作用的定量图像 ( 1 – 4）。PIXEL 方法为在这些结构中观察到的分子二聚体提供分子间相互作用能。通过电子密度分布的拓扑分析，使用分子中原子 (AIM) 方法研究了 (3, -1) 键临界点的分子间相互作用的性质和强度。拓扑参数表明分子间相互作用被归类为闭壳相互作用，并且使用 NCI 图来识别所涉及的非共价相互作用的性质。因此，详细的计算分析可以深入了解当前研究中结构固态中不同非共价相互作用的电子特性。
• Computational Study of the Formation of Short Centrosymmetric N–H···S Supramolecular Synthon and Related Weak Interactions in Crystalline 1,2,4-Triazoles
  作者：Dhananjay Dey、T. P. Mohan、B. Vishalakshi、Deepak Chopra

  DOI：10.1021/cg501103c

  日期：2014.11.5

  A comprehensive analysis of the crystal packing and the energetic features of a series of four biologically active molecules belonging to the family of substituted 4-(benzylideneamino)-3-(4-fluoro-3-phenoxyphenyl)-1H-1,2,4-triazole-5-(4H)-thione derivatives have been performed based on the molecular conformation and the supramolecular packing. This involves the formation of a short centrosymmetric R-2(2)(8) NH...S supramolecular synthon in the solid state, including the presence of CH...S, CH...O, CH...N, CH...F, CH...Cl, CF...FC, CCl...ClC, and CH...pi intermolecular interactions along with pp stacking to evaluate the role of noncovalent interactions in the crystal. The presence of such synthons has a substantial contribution toward the interaction energy (-18 to -20 kcal/mol) as obtained from the PIXEL calculation, wherein the Coulombic and polarization contribution are more significant than the dispersion contribution. The geometrical characteristics of such synthons favor short distance, and the population of related molecules having these geometries is rare as has been obtained from the Cambridge Structural Database (CSD). Furthermore, their interaction energies have been compared with those present in our molecules in the solid state. The topological characteristics of the NH...S supramolecular synthon, in addition to related weak interactions, CH...N, CH...Cl, CF...FC, and CCl...ClC, have been estimated using the quantum theory of atoms in molecules (QTAIM). In addition, an analysis of the Hirshfeld surface and associated fingerprint plots of these four molecules also have provided a platform for the evaluation of the contribution of different atom...atom contacts, which contribute toward the packing of the molecules in solids.
• 4-amino-5-(4-fluoro-3-phenoxyphenyl)-4H-1,2,4-triazole-3-thiol derivatives as antifungal agents
  申请人：KING FAISAL UNIVERSITY

  公开号：US11926602B1

  公开（公告）日：2024-03-12

  Antifungal compounds and, particularly, to antifungal compounds that are 4-amino-5-(4-fluoro-3-phenoxyphenyl)-4H-1,2,4-triazole-3-thiol derivatives and their use as antifungal agents.