1 Theoretical and Computational Chemistry Unit; 2 Department of Chemical Sciences, Adekunle Ajasin University, Akungba-Akoko, Ondo State, Nigeria
3 Department of Chemistry, University of Ibadan, Oyo State, Nigeria
4 Department of Chemistry, Adeyemi College of Education, Ondo, Ondo State, Nigeria
5 Phystech School of Biological and Medical Physics, Center for Educational Programs in Bioinformatics, Moscow Institute of Physics and Technology, Dolgoprudny, Russia
6 Chemistry Unit, Department of Physical Sciences, College of Natural and Applied Sciences, Wesley University, Ondo, Nigeria
The structure-property relationship is important in understanding molecular behaviors and their best-fit areas of applications. 3-(4-hydroxyphenyl) prop-2-en-1-one 4-phenyl Schiff base and some of its derivatives were optimized via the density functional theory with Becke three Lee Yang Parr correlation and 6-31G* basis set. The molecular properties calculated were the energies of the frontier molecular orbitals [highest occupied molecular orbital, lowest unoccupied molecular orbital, energy bandgap (Eg), chemical hardness, softness and hyperpolarizabilities (β)]. The electronic transitions were calculated with the time-dependent density functional theory methods, the absorption maxima (λabs), vertical transition energies (ΔEge), oscillator strengths and molecular orbital components with their percentage contributions were obtained. The anti-microbial efficacy of the molecules was tested against Staphylococcus aureus aminopeptidase S (AmpS) active site to predict the binding affinities. ADMEtox parameters of all the molecules were also investigated. Eg values ranged from 3.13 to 3.95 eV, β values ranged from 1.45 to 5.81×10-30 esu, and their binding affinities ranged from -4.57 to -6.12 kcal/mol, all were more than that of standard drug, streptomycin (-4.31 kcal/mol). The number of hydrogen bond donors and hydrogen bond acceptors were ranged from 1 to 2 and 3.75 to 5.25, respectively. Variations observed from the calculated molecular properties are the result of varying substituent groups. The molecules can be used as nonlinear optical materials and also showed potential for being effective against Staphylococcus aureus.