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<p>Polymorphism is the exciting feature of compounds existing in different crystalline forms. The present research is focused on the two polymorphic forms, <b>3A</b> and <b>3B</b>, of (<i>E</i>)-1-(3-hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one obtained by the Claisen-Schmidt condensation reaction of 1-(3-hydroxyphenyl)ethan-1-one and 1-naphthaldehyde. Both polymorphic forms were characterized by single-crystal X-ray diffraction (SC-XRD) analysis. The supramolecular assemblies of these polymorphic forms were found to be stabilized by various intermolecular interactions as revealed by the Hirshfeld surface analysis. The interaction energy calculations were carried out at the B3LYP/6-31G(d, p) level to further investigate the supramolecular assembly of these polymorphs. Moreover, antifungal, antibacterial, and antioxidant activities of these polymorphs were investigated, showing reasonable and slightly different potential of both polymorphs in these areas. Also, density functional theory (DFT) study of both polymorphs was performed, using the B3LYP-GD3/6-311 + + G(d, p) approach, with the analysis of Natural Bond Orbital (NBO) charges and donor-acceptor interactions, frontier molecular orbitals (FMOs), molecular electrostatic potentials (MEP), non-covalent interactions (NCI), Laplacian bond orders, localized orbital locator (LOL), and global reactivity parameters (GRPs). The obtained results provided support for the SC-XRD and Hirshfeld surface analysis results. Next, the quantum theory of atoms in molecules (QTAIM) and NCI analyses of the <b>3A</b> and <b>3B</b> crystal structures fragments provided strong support for the existence of off-set π<InlineEquation ID="IEq1"> <EquationSource Format="TEX">\(\:\cdots\:\)</EquationSource> </InlineEquation>π stacking interactions and C-H⋯π interactions and hydrogen bonds in the <b>3A</b> and <b>3B</b> crystal structures.</p>

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Two polymorphs of the 1-naphthaldehyde-based chalcone: synthesis, single-crystal X-ray characterization, Hirshfeld surface analysis, biological potential evaluation, and DFT study

  • 期刊论文

  • 发表日期：

    2026年5月2日

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  • Muhammad Ibrahim,
  • Akbar Ali,
  • Kainat Zohra,
  • Muhammad Ashfaq,
  • Muhammad Nawaz Tahir,
  • Necmi Dege,
  • Aleksey Kuznetsov,
  • Olívia Moreira Sampaio,
  • Lucas Campos Curcino Vieira,
  • Mohammed A. Assiri

摘要

Polymorphism is the exciting feature of compounds existing in different crystalline forms. The present research is focused on the two polymorphic forms, 3A and 3B, of (E)-1-(3-hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one obtained by the Claisen-Schmidt condensation reaction of 1-(3-hydroxyphenyl)ethan-1-one and 1-naphthaldehyde. Both polymorphic forms were characterized by single-crystal X-ray diffraction (SC-XRD) analysis. The supramolecular assemblies of these polymorphic forms were found to be stabilized by various intermolecular interactions as revealed by the Hirshfeld surface analysis. The interaction energy calculations were carried out at the B3LYP/6-31G(d, p) level to further investigate the supramolecular assembly of these polymorphs. Moreover, antifungal, antibacterial, and antioxidant activities of these polymorphs were investigated, showing reasonable and slightly different potential of both polymorphs in these areas. Also, density functional theory (DFT) study of both polymorphs was performed, using the B3LYP-GD3/6-311 + + G(d, p) approach, with the analysis of Natural Bond Orbital (NBO) charges and donor-acceptor interactions, frontier molecular orbitals (FMOs), molecular electrostatic potentials (MEP), non-covalent interactions (NCI), Laplacian bond orders, localized orbital locator (LOL), and global reactivity parameters (GRPs). The obtained results provided support for the SC-XRD and Hirshfeld surface analysis results. Next, the quantum theory of atoms in molecules (QTAIM) and NCI analyses of the 3A and 3B crystal structures fragments provided strong support for the existence of off-set π \(\:\cdots\:\) π stacking interactions and C-H⋯π interactions and hydrogen bonds in the 3A and 3B crystal structures.