Structural and Electronic Insights into Arylalkanones from Myristica ceylanica

A phytochemical investigation of Myristica ceylanica resulted in the identification of seven arylalkanone-derived phenolic compounds, comprising one new naturally occurring arylalkanone (A), two derivatives (A1 and A2) prepared by chemical synthesis, and four known malabaricones (B–E). Density functional theory (DFT) calculations were conducted to evaluate the geometries, electronic properties, and charge distributions of the newly identified arylalkanone and its derivatives and to compare them with those of malabaricones B–E. The arylalkanones exhibited geometrical features comparable to those of the malabaricones, whereas frontier molecular orbital analysis revealed similar HOMO–LUMO energy gaps for the malabaricones but a progressive widening of the gap among the arylalkanone derivatives, indicating enhanced electronic stabilisation. Mulliken population analysis identified oxygen atoms as the principal electron-rich sites in both series, with arylalkanones displaying greater charge polarisation and increased sensitivity to structural substitution.