Synthesis, structural, vibrational, molecular docking and nonlinear optical studies of (E)-N′-(2,3-dimethoxybenzylidene)-4-fluorobenzohydrazide

Jeeva P, Barathi D*, Rajaboopathi Mani, David Stephen A, Marjatta Louhi-Kultanen, Vinitha G, Abdullah G. Al-Sehemi

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

7 Citations (Scopus)
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Organic nonlinear optical single crystals of (E)-N′-(2,3-dimethoxybenzylidene)-4-fluorobenzohydrazide (DMB-FBH) were synthesized and grown using slow evaporation crystallization from ethanol solution. The single crystal X-ray diffraction scattering revealed that the DMB-FBH crystallised in the tetragonal crystal system with a centro symmetric space group of I 41/a. The crystallographic bond lengths and bond angles were compared with the values generated from optimized molecular geometry based on quantum chemical calculations. The functional group vibrations were identified theoretically by density functional theory with B3LYP 6–311 G (d,p) basis set using Gaussian 09 software package and their vibrations were compared with the experimental FT-IR spectra. The UV-visible and the fluorescence emission spectra of the DMB-FBH in aqueous solutions were recorded. The HOMO-LUMO energy level pictogram addressed the intramolecular charge transfer (ICT) interaction between donor and acceptor moieties and their impact on the energy gap was determined. Different interactions such as O···H, N···H, C···C and C···H in DMB-FBH were quantified via fingerprint plots and these results were compared with that of similar structure. The detailed molecular docking simulation was carried out with M. tuberculosis protein [PDB ID:2 × 22]. The third order nonlinear optical susceptibility (χ3) of DMB-FBH was confirmed experimentally by Z-scan method and their conversion efficiency was higher than the other hydrazones derivatives. In short, this work discusses the crystal structure, identification and quantification of the molecular interactions, thermal, antimycobacterial and optical properties of new hydrazone derivative.

Original languageEnglish
Article number132375
Number of pages14
JournalJournal of Molecular Structure
Early online date9 Jan 2022
Publication statusPublished - 15 Apr 2022
MoE publication typeA1 Journal article-refereed


  • Crystal structure
  • Crystallization
  • Density functional theory
  • Hydrazone
  • Third harmonic generation
  • Vibrational analysis


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