Double-headed schiff bases of naphthalene-fused disalicylaldehydes: Synthesis, structural analysis and theoretical studies

Novikov A. S., Khrustalev V. N., Novikov A. P., Kubasov A. S., Dukhnovsky E. A., Kritchenkov A. S., ...More

Journal of Molecular Structure, vol.1347, 2025 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 1347
  • Publication Date: 2025
  • Doi Number: 10.1016/j.molstruc.2025.143329
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Keywords: Disalicylaldehydes, Hydrogen bonds, Noncovalent interactions, Schiff bases
  • Open Archive Collection: Article
  • Azerbaijan State University of Economics (UNEC) Affiliated: Yes

Abstract

The synthesis and structural features of symmetrical double-headed Schiff bases of naphthalene-fused disalicylaldehydes were discussed for the first time. Results of X-ray diffraction analysis reveal that all discussed compounds contain short intramolecular hydrogen bonds of the O[sbnd]H···N, N[sbnd]H···O, and/or C[sbnd]H···N type (the first two contacts are the key structural feature of these molecules, determining their planar structures extending over the imine linkage and leading to the formation of pseudo-six-membered rings), and molecules of studied substances are interconnected by external hydrogen bonds of the C[sbnd]H···O and/or C[sbnd]H···N type in layers or columns in the solid-state. The analysis of Hirshfeld surfaces for the obtained crystal structures shown that in all cases crystal packing dictated mainly by interatomic contacts H···H and C···H.