Design, synthesis, X-ray structure, Hirshfeld surface, and NLO behavior of
Souheyla Chetioui1, Mansour Azayez2, Ouarda Brihi3
1VEHDD Laboratory, University of M'sila, University Pole, Road Bourdj Bou Arreiridj, 28000 M'sila, Algeria; Research Unit for Chemistry of the Environment and Molecular Structural. University of Constantine 1, 25000 Constantine, Algeria.
Abstract:
The crystalline form of the compound, 3-bromo-2-[(2E)-2-(2-oxonaphthalen-1(2H)-ylidene)hydrazinyl]benzoic acid (BOHB), has been synthesized in good yield by diazotization of 2-amino-3-bromobenzoic acid followed by a reaction with β-naphthol. The XRD-crystal measurements and DFT calculations confirmed that the hydrazone was the favored form. The structure of the synthetic product was also examined by IR and NMR spectroscopic methods. Using Hirshfeld surface analysis, interactions in the crystal have been highlighted, where many contributors are identified such as H···H (24.7%), O···H/H···O (20.6%), H···C/C···H (17.0%), and Br···H/H···Br (15.0%). Furthermore, the novel benzoic acid derivative was investigated for its nonlinear optical (NLO) properties. Computational results indicate that the compound shows enhanced first hyperpolarizability values relative to common reference systems. This suggests the benzoic acid derivative might offer a potential structural basis for exploring materials for selected NLO applications.
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