Synthesis, spectroscopic characterizations and structural analysis of (E)-1-(4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)-3-phenylprop-2-en-1-one
Journal of Molecular Structure, cilt.1376, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1376
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.molstruc.2026.147033
- Dergi Adı: Journal of Molecular Structure
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC, Academic Search Ultimate (EBSCO), Engineering Source (EBSCO)
- Anahtar Kelimeler: Chalcone, Hirshfeld surface analysis, NLO, Spectroscopy, Theoretical calculations, X-ray
- Ondokuz Mayıs Üniversitesi Adresli: Evet
Özet
A new piperazine-based chalcone derivative, 1-phenyl-3-[4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl]prop-2-en-1-one, was synthesized through a Claisen–Schmidt condensation between benzaldehyde and 4′-[4-(2-hydroxyethyl)piperazin-1-yl]acetophenone. The compound was isolated in high purity and fully characterized by FT-IR, ¹H, and APT-¹³C NMR spectroscopy, confirming the α,β-unsaturated carbonyl chalcone framework. Distinct spectral features, including the conjugated C=O stretch (1642 cm⁻¹) and trans-CH=CH coupling (J ≈ 15 Hz), supported the expected E-configuration. X-ray diffraction analysis indicated that the title compound crystallizes in the monoclinic space group P21/c with unit cell parameters of a=19.705(3) Å, b=8.7029(12) Å, c=10.8375(14) Å, and β=105.341(5) °.The molecular geometry obtained from single-crystal X-Ray diffraction was compared with results from Hartree–Fock and density functional theory calculations at the 6-311G+(d,p) level, showing reasonable agreement. Molecular electrostatic potential, frontier molecular orbital, and Hirshfeld surface analyses further illustrated the charge distribution and intermolecular interactions. Thermal stability and non-linear optical properties were also investigated, providing preliminary insight into the electronic and intermolecular characteristics of the chalcone framework and identifying the synthesized compound as a promising candidate for nonlinear optical (NLO) applications.