Algerian Journal of Sciences
Volume 0, Numéro 0, Pages 42-55
2024-07-04

Synthesis, X‐ray Structure, Hirschfield Surfaces Analysis And Dft Computations Of New Schiff Bases



Authors : Madani Abdelghani . Bouchama Anis . Hellal Abdelkader .

Abstract

The novel Schiff base compound named as 3-[(1Z)-N-(4'-aminobiphenyl-4-l)ethanimidoyl]-2-hydroxy-6-methyl-4H-pyran-4-one is synthesized by the chemical reaction of benzidine and acid déhydroacitic acid (DHA) in absolute ethanol under reflux condition, and the structure of the titled compound is verified and characterized by infrared, ultraviolet-visible (UV-vis) spectroscopies and the single-crystal X-ray diffraction technique. The compound crystallized in the monoclinic system, space group C 2/c, with the following unit cell parameters a=14.175(2), b=5.736(2) and c=21.150(2) A° and α =90°, β=107.5(6)°, ɣ=90° and Z=4 , V= 1602.45(10) (Å3), T = 170(2)K, The final R1 was 0.0482 (I > 2σ(I)) and wR2 was 0.1395 (all data). The structure for the C20H18N2O3 was examined using Hirschfield topology analysis and Density Functional Theory (DFT) calculations a detailed study based on B3LYP/6-311G (d, p). The graphical tools based on Hirschfield surfaces and two-dimensional (2D) fingerprint plots have proven useful for visualize and analyze intermolecular interactions in polymorphs of molecular crystals. The optimized geometry, global reactivity descriptors, and HOMO-LUMO orbitals of the molecule were computed using the DFT-B3LYP method and discussed to evaluate the chemical reactivity and charge distribution on the molecule. The theoretical bond lengths and angles for the C20H18N2O3 wereobtained by using the B3LYP level of density function theory (DFT) with B3LYP /6-311G (d, p) basis sets. These results showed very good agreement with the experimental X-ray values.

Keywords

Benzidine, Schiff base, Crystal structure, Hirschfield surfaces, DFT

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