IR spectrum and normal mode analysis of the antiAlzheimer's disease natural product Huperzine A: A quantum chemistry density-functional theory (DFT) investigation

Abstract

Quantum chemistry density-functional theory (DFT)B3LYP method with 6-31G basis set has been empolyed to study the electronic structure and IR spectrum of Huperzine A. The calculation result showed that the characteristic of the predicted IR bands was in general consistent with the experimental spectrum. 45 vibration modes were assigned clearly from the total of 102 vibration bands. The strongest IR-intensive band corresponds to the stretching vibration of the C=O bond of the pyridone ring, and the highest frequency band belongs to the pyridone N-H stretch. The investigation showed that the obvious differences between the calculated bands and the experimental spectrum existed at the bands involving the hydrogen atoms of amino and pyridone amide groups, which could form intermolecular hydrogen bond with other Huperzine A in the crystal structure. The hydrogen bonds can not only affect the orientation of these hydrogen atoms, but also can affect the force property of the chemical bond, which can change the vibrational frequencies.