Synthesis, spectroscopic characterization, DFT calculations, and molecular docking studies of new unsymmetric bishydrazone derivatives

Kaya Y., Erçağ A., Serdaroğlu G., Kaya S., Grillo I. B., Rocha G. B.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1244, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1244
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.molstruc.2021.131224
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Isatin bishydrazones, DFT, PRIMorDIA, Chemical reactivity, Electronic structure principles, TRANSITION-METAL-COMPLEXES, ELECTRONIC-STRUCTURE, LATTICE ENERGIES, MAXIMUM HARDNESS, MANNICH-BASES, BASIS-SET, FT-IR, ISATIN, SCHIFF, NMR
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

Three new unsymmetric isatin bishydrazone compounds; Comp. I, II, III, were synthesized by the condensation of 3,5-dichloro-salicylaldehyde, 3-bromo-5-chloro-salicylaldehyde, and 3,5-dibromo-salicylaldehyde with isatin monohydrazone, respectively. The synthesized compounds were characterized by elemental analysis, H-1-NMR, FT-IR, UV-Vis spectroscopy, and mass spectrometry technique. For studied molecules, chemical parameters like frontier orbital energies, energy gap, electronegativity, chemical potential, chemical hardness, softness, electrophilicity, nucleophilicity, electrodonating power, electroaccepting power, polarizability, and dipole moment were calculated and discussed. Investigating the validity of well-known electronic structure principles like Maximum Hardness, Minimum Polarizability, and Minimum Electrophilicity Principles in the study, it was determined which compound is more stable compared to others. In recent days, a new software having PRIMorDIA name was developed to explore reactivity and electronic structure in large biomolecules by some of the authors of this paper. Molecular docking studies for these newly synthesized molecules were performed using PRIMorDIA software. Considering the intramolecular interactions, NBO analyzes of three bishydrazone derivatives were conducted to evaluate the chemical behavior. (C) 2021 Elsevier B.V. All rights reserved.