Scholarlink

<p>In this work, we report the synthesis, crystal structure, and comprehensive experimental and theoretical investigation of 2-(4-nitrophenyl)-2-oxoethyl-4-nitrobenzoate, a nitroaromatic phenacyl ester of structural and electronic interest. Single-crystal X-ray diffraction reveals that the compound crystallizes in the monoclinic system with space group <i>P2₁/n</i>, and the crystal packing is governed by a combination of C–H···O hydrogen bonds, O···π interactions, and π–π stacking. Hirshfeld surface analysis and two-dimensional fingerprint plots were employed to visualize and quantify the intermolecular contacts responsible for the supramolecular architecture. Interaction energy calculations and three-dimensional energy frameworks further demonstrate that dispersion forces dominate the stabilization of the crystal packing. Density functional theory (DFT) calculations at the B3LYP/6-311 + G(d, p) level were performed to investigate the optimized molecular geometry, frontier molecular orbitals, molecular electrostatic potential, and global reactivity descriptors, providing insight into the electronic structure and charge distribution of the molecule. Natural bond orbital (NBO) analysis reveals significant intramolecular charge-transfer interactions associated with conjugation between the aromatic, carbonyl, and nitro groups. To explore possible interaction behaviour at the biomolecular level, molecular docking and molecular dynamics simulations were carried out against the SARS-CoV-2 main protease (MPro, PDB ID: 5R7Y), revealing stable binding of the ligand within the active site over a 100 ns simulation. In addition, in silico ADME-T and drug-likeness predictions indicate favourable pharmacokinetic properties and compliance with Lipinski’s rule of five. Overall, this combined structural and computational study establishes a clear relationship between the molecular structure, electronic features, and interaction characteristics of the title compound, highlighting its relevance as a structurally and electronically interesting molecular scaffold.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Crystal structure, intermolecular interactions and DFT studies of 2-(4-nitrophenyl)-2-oxoethyl-4-nitrobenzoate

  • 期刊论文

  • 发表日期：

    2026年3月26日

查看全文
  • Dileep Chikkur Shanthakumar,
  • Sahana Doreswamy,
  • Lohith Tumakuru Nagarajappa,
  • Sandhya Rani Nagarajaiah,
  • Chirag Shivakumara,
  • Srikantamurthy Ningaiah,
  • Sridhar Mandayam Anandalwar

摘要

In this work, we report the synthesis, crystal structure, and comprehensive experimental and theoretical investigation of 2-(4-nitrophenyl)-2-oxoethyl-4-nitrobenzoate, a nitroaromatic phenacyl ester of structural and electronic interest. Single-crystal X-ray diffraction reveals that the compound crystallizes in the monoclinic system with space group P2₁/n, and the crystal packing is governed by a combination of C–H···O hydrogen bonds, O···π interactions, and π–π stacking. Hirshfeld surface analysis and two-dimensional fingerprint plots were employed to visualize and quantify the intermolecular contacts responsible for the supramolecular architecture. Interaction energy calculations and three-dimensional energy frameworks further demonstrate that dispersion forces dominate the stabilization of the crystal packing. Density functional theory (DFT) calculations at the B3LYP/6-311 + G(d, p) level were performed to investigate the optimized molecular geometry, frontier molecular orbitals, molecular electrostatic potential, and global reactivity descriptors, providing insight into the electronic structure and charge distribution of the molecule. Natural bond orbital (NBO) analysis reveals significant intramolecular charge-transfer interactions associated with conjugation between the aromatic, carbonyl, and nitro groups. To explore possible interaction behaviour at the biomolecular level, molecular docking and molecular dynamics simulations were carried out against the SARS-CoV-2 main protease (MPro, PDB ID: 5R7Y), revealing stable binding of the ligand within the active site over a 100 ns simulation. In addition, in silico ADME-T and drug-likeness predictions indicate favourable pharmacokinetic properties and compliance with Lipinski’s rule of five. Overall, this combined structural and computational study establishes a clear relationship between the molecular structure, electronic features, and interaction characteristics of the title compound, highlighting its relevance as a structurally and electronically interesting molecular scaffold.