A new derivative of 1-allyl-3-methylimidazolium chloride as ionic liquid compound: Synthesis, physical properties and DFT studies

YILDIZ M., Gümüştaş S., Kınal A., ALP S.

Journal of Molecular Structure, cilt.1321, 2025 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1321
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2024.140110
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Ionic liquids, 1-Allyl-3-methylimidazolium chloride, Ion-pair dimers, DFT, ESP, NBO
  • Dokuz Eylül Üniversitesi Adresli: Evet

Özet

This study aimed to improve the physical properties of 1-allyl-3-methylimidazolium chloride (AMIMCl) by synthesizing a new derivative, 1-allyl-2-hydroxymethyl-3-methylimidazolium chloride (AHMMIMCl). The synthesized AHMMIMCl was characterized using FT-IR, 1HNMR, 13CNMR, TGA, and DSC techniques, and its physical and computational properties were compared with those of AMIMCl. Experimentally, AHMMIMCl exhibited a lower viscosity (Δη =267.57 cP), a significantly reduced melting point (ΔT =∼100 °C), and lower conductivity (Δσmax=30.72 mS.cm−1 at 25 °C). The stable geometries of the cations, ion-pairs, and dimer structures were estimated employing DFT methods. The nature of the cation–anion interaction was analyzed by the natural bond orbital (NBO) and electrostatic potential (ESP) analyses. The physical properties of the newly synthesized compound are found to be in agreement with DFT calculations. Additionally, the new derivative demonstrated enhanced viscosity and melting point compared to the parent compound (AMIMCl), with no significant alteration observed in the hydrogen bond length within the anion-cation interaction. These results indicate the potential applicability of the new product as a substitute for AMIMCl.