Synthesis, Characterization, and Hirshfeld Surface Analysis of Two Schiff Bases: (E)-3-(((4-iodophenyl)imino)methyl)Benzene-1,2-Diol and (E)-3-(((3-bromo-4-methylphenyl)imino)methyl)-Benzene-1,2-Diol

Şimşek O., Atalay Ş., Taşdoğan M., Ağar E., Bülbül H., KANSIZ S.

Journal of Structural Chemistry, cilt.67, sa.4, ss.827-840, 2026 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 67 Sayı: 4
  • Basım Tarihi: 2026
  • Doi Numarası: 10.1134/s0022476626040116
  • Dergi Adı: Journal of Structural Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, INSPEC
  • Sayfa Sayıları: ss.827-840
  • Anahtar Kelimeler: benzaldehyde, bromine, crystal structure, Hirshfeld surface, iodophenyl, Schiff base
  • Samsun Üniversitesi Adresli: Evet

Özet

Abstract: The title compounds, (E)-3-(((4-iodophenyl)imino)methyl)benzene-1,2-diol compound 1 and (E)-3-(((3-bromo-4-methylphenyl)imino)methyl)benzene-1,2-diol 2 are synthesized and comprehensively characterized through spectroscopic and crystallographic techniques, including single crystal X-ray diffraction, IR, UV-Vis, 1H NMR, and 13C NMR analyses. Both compounds adopt an E configuration with respect to the C=N double bond and crystallize in the triclinic crystal system, space group. Their crystal packings are primarily stabilized by O−H⋯O hydrogen bonds, complemented by C–H⋯π interactions, which extend the packing into a three-dimensional supramolecular framework. Hirshfeld surface analysis is employed to identify regions of potential hydrogen-bond formation and to quantify the relative contribution of different intermolecular contacts. The results reveal that C⋯H interactions dominate the surface contributions, underscoring their importance in the overall packing stability and molecular arrangement.