Synthesis, X-ray crystal structure, Hirshfeld analysis and computational investigation of bis(methylthio)acrylonitrile with antimicrobial and docking evaluation

In this investigation, we studied the reactivity of 3-oxopropanenitrile derivatives 3 with CS2 in the presence of sodium hydride to give the acrylonitrile potassium salt intermediate 4 which the easily reacted with methyl iodide to afford the corresponding 2-(3-methylbenzofuran-2-carbonyl)-3,3-bis(methylthio)acrylonitrile ( 5 ). The reactants were optimized utilized B3LYP/6-311(G) to elucidate their physical descriptors of them and confirm the stability of compound 5 and its reactivity due to presence of different reactive sites using FMO, ESP and MEP. Moreover, the crystal structure of bis(methylthio)acrylonitrile derivative 5 showed a triclinic structure and P-1 space group, also Hirshfeld analysis of 5 reveled contacts (H....H) with (43.1%), H....C/H....N/H...O/H....S with contributed 4.8%, 5.2, 3.5 and 4.0%, respectively. It also showed higher intramolecular interaction in its molecular packing of strong acceptor-donor interaction in C4-H4A center dot center dot center dot N1i with distance of 3.423A and angle = 134.58(o) . The comparative study between experimental and theoretical results according to its bond length, bond angles, 1HNMR and 13CNMR were in strong correlation with DFT/B3LYP/6-311(G) basis set. Moreover, compound 5 exhibited higher antimicrobial activities when compared with different standard drugs which was confirmed via molecular docking with different types of proteins. (C)& nbsp;2022 Elsevier B.V. All rights reserved.

Automated summary

In this investigation, we studied the reactivity of 3-oxopropanenitrile derivatives with CS2 in the presence of sodium hydride. The resulting compound showed promising antimicrobial activities. The study utilized computational and experimental methods to elucidate the structure and reactivity of the compound.