Structural and Quantum Study of Newly Synthesized Methyl(𝑍)-۳-((۴-Fluorophenyl) Amino) But-۲-Enoate

Compound C۱۱H۱۲NO۲F was obtained by reacting of ۴-fluoroaniline with methyl acetoacetate, using CoCl۲ 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 P۲۱/c space group, which is symmetrical and monoclinic (Z=۴) [a=۶.۵۹۱۹(۳)Å, b=۱۵.۹۸۰۹(۸)Å, c=۱۰.۱۸۵۹(۴)Å, β=۱۰۵.۳۳۰۰(۱۶) °; V =۱۰۳۴.۸۵ Å۳]. The crystal structure consists of alternating up and down C۱۱H۱۳NO۲F 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 B۳LYP function and the ۶-۳۱۱+ G(۲d,۳p) 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 (۴۶.۷%), O ···H (۱۶.۷%), and F ···H (۱۴.۲%) contacts are the dominant interactions in the crystal packing of the investigated molecule.

کلیدواژه ها:

β-enaminoesters ، X-ray diffraction ، Hydrogen bonds analysis ، DFT ، Hirshfeld