Experimental and computational studies of 3-(N-morpholinylcarbodithioate)-2-(4-methoxyphenyl)chroman-4-one, a flavanone with potential therapeutical properties

Abstract

In this paper we are reporting the results obtained regarding 3-(N-morpholinylcarbodithioate)-2-(4-methoxyphenyl)chroman-4-one, mainly by IR and NMR spectroscopy combined with Density Functional Theory calculations. The structural and vibrational characterization of this synthetic flavanone was carried out by performing quantum mechanical calculations in the ground state and by using several hybrid functionals (B3LYP, PBE1PBE, CAM-B3LYP and ωB97X-D) in conjunction with the same basis set, namely 6-311G(d,p). A complete assignment of all the absorption bands present in the vibrational spectrum has been performed.The theoretical 1H and 13C NMR chemical shifts (with respect to TMS) of both isomers of the investigated flavanone were obtained with four DFT-GIAO functionals, i.e. B3LYP, WP04, WC04 and PBE1PBE, in conjunction with the 6-311++G(d,p) and cc-pVDZ basis sets. The values of the theoretical 1H and 13C NMR chemical shifts have been compared with the experimental ones. The effect of different functionals and basis sets on the accuracy and precision in predicting the1H and 13C NMR chemical shifts was also assessed.The chemical potential and oral bioavailability of the studied compound was explored by computing several quantum molecular descriptors that characterize the electronic interactions between a compound and its biological receptor, such as the dipole moment, the energy of frontier molecular orbitals, the gap energy, the electronegativity, the chemical hardness/softness and the electrophilicity index. The druglikeness of the targeted compound was evaluated by using filters known to be efficient in estimating the potential of a molecule to be a bioavailable oral drug.