A theoretical assessment of the structural and electronic features of some retrochalcones

Abstract

AbstractIn the present work, six retrochalcones, namely echinatin, licochalcone A, B, C, D and E, have been studied using density functional theory at the B3LYP/6‐311++G** level. A comparative analysis of the non‐linear optical properties has been performed with two prototype standard molecules, urea and para‐nitroaniline. The computed first pKa values of all the deprotonation sites lie in the range of 8.9‐10.0, which suggests the predominance of the neutral form of the considered retrochalcones at the physiological pH. Further, the second pKa values of the hydroxyl groups of the mono‐anionic forms lie in the range of 10.0‐11.6 and the third pKa values for deprotonation from the dianionic forms of licochalcone B and D are ~17. Moreover, the electronic spectra, frontier molecular orbitals analysis and molecular electrostatic potential maps have been analyzed for a better understanding of the electro‐optical properties of the compounds under study.