Two new Schiff bases of (E)-2,4-di-tert-butyl-6-((4-fluorophenylimino)methyl)phenol (I) and (E)-2,4-di-tert-butyl-6-((3-iodo-4-methylphenylimino)methyl)phenol (II): structural, spectroscopic and quantum chemical calculations

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Güzel E., Macit M., Ergüzeloğlu E., Kalecik S., Keleşoğlu Z., Yavuz M.

Molecular Crystals and Liquid Crystals, cilt.763, sa.1, ss.96-113, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 763 Sayı: 1
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1080/15421406.2023.2199185
  • Dergi Adı: Molecular Crystals and Liquid Crystals
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Chemical Abstracts Core, Communication Abstracts, Compendex, INSPEC, Metadex, Civil Engineering Abstracts
  • Sayfa Sayıları: ss.96-113
  • Anahtar Kelimeler: DFT, Hirshfeld surface, optical energy band, spectroscopic data, XRD
  • Atatürk Üniversitesi Adresli: Evet

Özet

In this study, two Schiff bases, (E)-2,4-di-tert-butyl-6-((4-fluorophenylimino)methyl)phenol (I) and (E)-2,4-di-tert-butyl-6-((3-iodo-4-methylphenylimino)methyl)phenol (II) are synthesized and characterized by XRD, FT-IR, UV-Vis and NMR techniques. (I) and (II) compounds display enol-imine form by O-H···N intramolecular hydrogen bonds. The title compounds are stabilized by C—H···π interactions. The presence of various inter molecular interactions and 2D-fingerprint regions are well supported by the Hirshfeld surface analysis. Also experimental optical energy band and gap studies are discussed. All chemical theoretical computations are calculated by Density Functional Theory (DFT) at B3LYP level by using 3-21 G basis set. Chemical activity analyses are showed that compounds have large energy gaps, higher values of hardness and lower values of softness support the title molecules are high kinetic stability. Also, chemical activity properties generate foresight about electrophilic and nucleophilic nature.