Structural Investigation and Hirshfeld Surface Analysis of Two [ONO]-Type Schiff Bases


Yeşilbağ S., KANSIZ S., Dege N., Ağar E.

Journal of Structural Chemistry, cilt.65, sa.3, ss.464-477, 2024 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 65 Sayı: 3
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1134/s0022476624030041
  • Dergi Adı: Journal of Structural Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Sayfa Sayıları: ss.464-477
  • Anahtar Kelimeler: crystal structure, Hirshfeld surface, NMR, ONO donor, Schiff base, XRD
  • Samsun Üniversitesi Adresli: Evet

Özet

Abstract: Two novel [ONO]-type tridentate Schiff base compounds namely (E)-2-(((2-hydroxyphenyl)imino) methyl)-4,5-dimethoxyphenol, C15H15NO4 (1), and (E)-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)-4,5-dimethoxyphenol, C15H14ClNO4 (2) were synthesized. These compounds were characterized using various spectroscopic techniques, including single crystal X-ray diffraction (XRD), infrared (IR), proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR), and UV-Vis spectroscopy. The X-ray crystallographic analysis revealed that both compounds 1 and 2 contain two independent molecules within the asymmetric unit. Compound 1 crystallizes in the orthorhombic system with the Pna21 space group, while compound 2 crystallizes in the monoclinic system with the P21/c space group. An important feature observed in the crystal structure of compound 1 is the presence of O–H···N and O–H⋯O hydrogen bonds. In compound 2, the hydrogen bonding interactions involve C–H⋯O, O–H⋯O and O–H⋯N. Additionally, both compounds exhibit C–H⋯π interactions. To further understand the bonding interactions in compounds 1 and 2, Hirshfeld surface analyses and 2D fingerprint graphs were performed. The results indicate that the Hirshfeld surfaces are predominantly influenced by H⋯H, O⋯H, and C⋯H contacts.