Synthesis, crystal structure, antioxidant activity and dft study of 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-One

Publication date: 5 January 2020Source: Journal of Molecular Structure, Volume 1199Author(s): Omar Alejandro Ramos Rodríguez, Nancy Evelyn Magaña Vergara, Juan Pablo Mojica Sánchez, María Teresa Sumaya Martínez, Zeferino Gómez Sandoval, Alejandro Cruz, Ángel Ramos OrganilloAbstractThe compound 2-aryl-2,3-dihydro-4H- [1,3]thiazino[3,2-a]benzimidazol-4-one (C16H12N2OS) (III) was synthesized. The compound crystallized in a monoclinic crystal system with P21/c space group as revealed by mono-crystal X-ray diffraction. The X-ray analysis and density functional theory complementary calculations showed that noncovalent C–H···π interactions between the benzimidazole system and the thiazine ring form a dimerization along the direction of the b axes, additionally π···π interactions were found between the benzene rings. The C12, in the thiazine ring, has a distortion angle (41.69°) respect to the plane of benzimidazole. The intermolecular interactions in the crystal structure were quantified and analyzed using Hirshfeld surface analysis. The predominant interaction within the crystalline structure was found to be H⋯H interaction. On the other hand, antioxidant activity of the C16H12N2OS system was studied using the DPPH and ABTS+ assay. Using the energy profile for the reaction of DPPH with III it was demonstrated that the antioxidant activity is carried out through HAT (H12) mechanism where conjugation of the radical can occur between the C12 of the thiazine ring a...
Source: Journal of Molecular Structure - Category: Molecular Biology Source Type: research