Comparative Experimental and Theoretical Study on the Structure of Potassium 2,4-Hexadienoate: Structure-Activity Relationship

Abstract

For the first time, a density functional theory (DFT) study was conducted on the structure of a well-known antibacterial agent namely potassium 2,4-Hexadienoate, in order to elucidate its vibrational, electronic and reactivity proprieties. Structure optimization was performed using three common hybrid functionals (DFT/ B3LYP-D3; DFT/ M05-2X and DFT/M06-2X) to identify the suitable functional. Geometric parameters, IR and UV-vis spectra were well reproduced when using DFT/M06-2X with 6-311(d)G+ basis set (R2 = 0.99913). The assimilation of IR frequencies has been achieved using potential energy distribution (PED)analysis at M06-2X/6-311(d) G + level. Time-dependent density functional theory (TD-DFT) and natural bond orbital (NBO) analysis were realized to identify the excited states of 2,4-Hexadienoate anion in the liquid phase, using the solute electron density solvation model (SMD). Moreover, reactive sites in the molecule were localized by molecular electrostatic potential (MEP) analysis. Highest Occupied Molecular Orbitals (HOMO), lowest Unoccupied Molecular Orbitals (LUMO) and energy gap (HOMO-LUMO gap), were used to calculate global reactivity descriptors (GRDs), according to the frontier molecular orbitals (FMO) theory, the resulting values were analyzed to explore the chemical reactivity of the molecule and elucidate the structure-activity relationship.