Shedding Light on the Synthesis, Crystal Structure, Characterization, and Computational Study of Optoelectronic Properties and Bioactivity of Imine derivatives

Abstract

Two imine compounds named as (E)-2-(((3,4dichlorophenyl)imino)methyl)phenol (DC2H) and (E)-4-(((2,4dimethylphenyl)imino)methyl)phenol (DM4H) are synthesized, and their crystal structures are verified using the single-crystal X-ray diffraction (XRD) technique. The crystal structures of the compounds are compared with the closely related crystal structures using the Cambridge Structural Database (CSD). The crystal packing in terms of intermolecular interactions is fully explored by Hirshfeld surface analysis. Void analysis is carried out for both compounds to check the strength of the crystal packing. Furthermore, a state-of-the-art dual computational technique consisting of quantum chemical and molecular docking methods is used to shed light on the molecular structure, optoelectronic properties, and bioactivity of indigenously synthesized compounds. The optimized molecular geometries are compared with their counterpart experimental values. Based on previous reports of biofunctions of the indigenously synthesized imine derivatives, they are explored for their potential inhibition properties against two very crucial proteins (main protease (M pro ) and nonstructural protein 9 (NSP9)) of SARS-CoV-2. The calculated interaction energy values of DC2H and DM4H with M pro are found to be −6.3 and −6.6 kcal/mol, respectively, and for NSP9, the calculated interaction energy value is found to be −6.5 kcal/mol. We believe that the current combined study through experiments and computational techniques will not only pique the interest of the broad scientific community but also evoke interest in their further in vitro and in vivo investigations.

Polymorphs of Substituted p-Toluenesulfonanilide: Synthesis, Single-Crystal Analysis, Hirshfeld Surface Exploration, and Theoretical Investigation

“…The overall interactions present in the single crystal can be fragmented in order to find the contribution of contacts in the crystal packing. − For that purpose, two-dimensional (2D) fingerprint plots are formed. Figure a,e,i shows the 2D plot of overall interactions in MSBT , MSBM , and DAYWUW , respectively.…”

Synthesis, Characterization, Crystal Structure and Computational Study of Third‐Order NLO Properties of Schiff bases

“…Figure 7 (a–b) represents the crystal voids in the crystal structure of 2AP6NO and 2AP4ETH . The voids are measured by assuming that all the atoms of a molecule are spherically symmetric [53–58] . The percentage of crystal void was calculated by the ratio of void volume to unit cell volume.…”

“…The voids are measured by assuming that all the atoms of a molecule are spherically symmetric. [53][54][55][56][57][58] The percentage of crystal void was calculated by the ratio of void volume to unit cell volume. The volume of 2AP6NO was found to be 1237.53 Å 3 and the void volume was 135.31 Å 3 , so the calculated void volume of compound 2AP6NO is 10.93 %.…”

Autocatalytic Green Synthesis of Imines in Traceless Medium

“…Imines (Schiff bases) are widely used as dyes, ligands, and intermediates for organic synthesis. [1][2][3][4] Some of them act as inhibitors of enzymes (e. g., the Mpro and NSP9 proteins of the SARS-CoV-2 virus [5] or urease [6] ) and exhibit antioxidant, antimicrobial, [7] anti-inflammatory, [8] and anticancer activities. [8][9][10] Generally, imines are synthesized by condensation of amines with carbonyl compounds or their precursors in organic solvents.…”