Structural and Quantum Study of Newly Synthesized Methyl(𝑍)-3-((4-Fluorophenyl) Amino) But-2-Enoate

Compound C11H12NO2F was obtained by reacting of 4-fluoroaniline with methyl acetoacetate, using CoCl2 as a catalyst. X-ray structural analysis identified the structure of the synthetized enaminoester, and infrared spectroscopy and proton NMR complemented it. The β-enaminoester crystallized in the P21/c space group, which is symmetrical and monoclinic (Z=4) [a=6.5919(3)Å, b=15.9809(8)Å, c=10.1859(4)Å, β=105.3300(16) °; V =1034.85 Å3]. The crystal structure consists of alternating up and down C11H13NO2F molecules staked along with the b-axis. Van der Walls interactions keep the crystal structure together by looking at the weak hydrogen bonds of the N-H-O and C-H-O types inside the molecule. A high-level Density Functional Theory computation was performed on the investigated molecule, which was found to have a substantial correlation with the experimental data. Because of their high accuracy in determining the geometric structure of molecules, the B3LYP function and the 6-311+ G(2d,3p) basis set were chosen. The molecule chemical reactivity was evaluated by creating its Frontier Molecular Orbitals (FMOs) and the Molecular Electrostatic Potential surfaces (MEP). The global reactivity descriptors were computed using the FMOs energy levels, gaining further insight into the molecule's reactivity. The local reactivity was assessed by calculating the Fukui functions and dual descriptor indices. Analyses of Hirshfeld surface mapped over dnorm and shape-index were further used to identify the intermolecular interactions. The fingerprint histograms allow to show that H ···H (46.7%), O ···H (16.7%), and F ···H (14.2%) contacts are the dominant interactions in the crystal packing of the investigated molecule.