Synthesis of a novel phenytoin derivative: Crystal structure, Hirshfeld surface analysis and DFT calculations

Hydantoin compounds are important heterocyclic scaffolds and a class of well-known bioactive molecules with a broad spectrum of pharmacological properties. Consequently, considerable efforts have been devoted to the design and synthesis of a broad range of hydantoin derivatives. In this context, the compound 3-allyl-5,5-diphenylimidazolidine-2,4-dione, C18H16N2O2 (3ADID) was synthesized and its structure was determined by X-ray structure analysis. Further, the molecular structure was examined using Hirshfeld topology analysis and Density Functional Theory (DFT)-B3LYP calculations with the basis set 6-311++G (d,p). In the title molecule, C18H16N2O2, the imidazolidine ring is planar with the allyl substituent oriented nearly perpendicular to it. In the crystal, hydrogen bonded chains of molecules are arranged in sets of three about the 3(2) axes by C-H center dot center dot center dot pi (ring) interactions. Hirshfeld surface map and 2D fingerprint plots were used to explore intermolecular interactions. The optimized geometry, global reactivity descriptors, and HOMO-LUMO orbitals of the molecule were computed by DFT and discussed. To evaluate the chemical reactivity and charge distribution on the molecule, molecular electrostatic potential (MEP) and atomic charges, computed by Mulliken population analysis and NBO theory were determined. The local reactivity was examined by determining the Fukui functions and dual descriptor indices. DFT calculations at the same level of theory, with the POP=NBO keyword, were used to evaluate charge delocalization and hyperconjugative interactions through Natural Bond orbital analysis. (c) 2019 Elsevier B.V. All rights reserved.