4-[(4-acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid, a newly synthesized amide with hydrophilic and hydrophobic segments: Spectroscopic characterization and investigation of its reactive properties

Abstract

The FT-IR and FT-Raman spectra of 4-[(4-acetylphenyl)amino]-2- -methylidene-4-oxobutanoic acid were recorded. The vibrational wave numbers were computed by DFT quantum chemical calculations and the vibrational assignments were realized using the potential energy distribution. The theoretically predicted geometrical parameters were in agreement with the XRD data. Determination and visualization of molecule sites prone to electrophilic attacks were performed by mapping the average local ionization energies (ALIE) to the electron density surface. Furthermore, determination of possible reactive centres of title molecule was realized by calculation of the Fukui functions. Intramolecular non-covalent interactions were also determined and visualized. In addition, prediction of molecule sites possibly prone to autoxidation was performed by calculation of the bond dissociation energies (BDE), while the stability of the title molecule in water was assessed by calculation of radial distribution functions (RDF) obtained after molecular dynamics (MD) simulations. The docked title ligand compound forms a stable complex with insulin receptor kinase and gives a binding affinity of –10.2 kcal* mol-1.

Keywords

• DFT
• ALIE
• BDE
• RDF
• molecular docking