NMR spectroscopic, mass spectroscopic, X-ray crystallographic, and theoretical studies of molecular mechanics of natural products: farformolide B and sesamin.

Two natural products, farformolide B and sesamin were isolated from Farfugium japonicum and Cinnamomum kanehirae, respectively. The structures of the two natural products, including their relative stereochemistry, were elucidated using spectroscopic data and theoretical calculations. The molecule 1 (farformolide B) is newly recognized by X-ray crystallography. The two compounds were also investigated by a theoretical analysis using the B3LYP/6-31G* method of the Gaussian 03 package program. The theoretical results were supplemented by experimental data to determine the optimal geometric structures of the two compounds. The calculated molecular mechanics were found to compare well with the experimental data. Several important thermodynamic properties of the two products, including ionization potentials, highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies, energy gaps, heat of formation, atomization energies, and vibration frequencies, were also calculated. The study also provided a good understanding of the stereochemical structure and thermodynamic properties of the two molecules.