Exploring Phenoxazinone Synthase Activities: Experimental and Theoretical Analyses of Symmetrical Azine Ligands

Meziane, Hanae; Abbaoui, Zakariae; Ouabane, Mohamed; Djedouani, Amel; Chetioui, Souheyla; El Kodadi, Mohamed; Touzani, Rachid; Belkhir, Hammouti; Bouachrine, Mohammed; Bougueria, Hassiba

doi:10.22036/pcr.2024.420037.2433

Exploring Phenoxazinone Synthase Activities: Experimental and Theoretical Analyses of Symmetrical Azine Ligands

Document Type : Regular Article

Authors

Hanae Meziane ¹

zakariae Abbaoui ¹

Mohamed Ouabane ²

Amel Djedouani ³

Souheyla Chetioui ⁴

Mohamed El Kodadi ⁵

Rachid Touzani ¹

Hammouti Belkhir ⁶

Mohammed Bouachrine ⁷

Hassiba Bougueria ⁸

¹ University Mohammed Premier, Faculty of Sciences, Laboratory of Environment and Applied Chemistry (LCAE), Oujda, Morocco.

² Molecular Chemistry and Natural Substances Laboratory (MCNSL), Department of Chemistry, Faculty of Sciences, Moulay Ismail University, BP 11201 Zitoune, Meknes-50000, Morocco.

³ Laboratory of Analytical Physical Chemistry and Crystallochemistry of Organometallic and Biomolecular Materials, University of Constantine 1, 25000, AlgeriaEcole Normale Supérieure de Constantine, Ville Universitaire Ali Mendjeli,

⁴ Research Unit of Environmental Chemistry and Structural Molecular (CHEMS), Faculty of Exact Sciences, Department of Chemistry, University of the Mentouri Brothers, Constantine 1, Constantine 25000, Algeria

⁵ Laboratory of Innovation in Science, Technology and Education (LIST), CRMEF Oriental, Oujda, Morocco.

⁶ FaculEuro-Mediterranean University of Fez (UEMF), BP. 15, 300700 Fez, Morocco.ty of Sciences

⁷ MCNS laboratory, CMC, Faculty of Science, Moulay Ismail University, Meknes, Morocco

⁸ Ecole Normale Supérieure de Constantine, Ville Universitaire Ali Mendjeli, 25000 Constantine, Algeria.

https://doi.org/10.22036/pcr.2024.420037.2433

Abstract

This study investigates the catalytic potential of five recently synthesised symmetrical azine ligands in combination with various metal salts in situ for the synthesis of phenoxazinone synthase. UV spectrometry was used to analyse the resulting complexes, all of which exhibited remarkable efficiency in catalysing the oxidation of aminophenol to phenoxazinone under ambient conditions. In particular, the pairing of the ligand L1 and CuCl2 in a 1:1 molar ratio ([1L/1M]) showed the highest catalytic performance. These results offer promising prospects for the application of these complexes as effective catalysts in various chemical processes. Furthermore, a Density Functional Theory investigation of the chemical reactivity of these ligands was carried out to determine various widely recognised quantum chemical descriptors, including hardness, chemical potential, electrophilicity indices and molecular orbital theory analysis. The study aimed to characterise nucleophilic, electrophilic, electron accepting and electron donating compounds.

Graphical Abstract