Relationship between molecular structure and Raman spectra of quinolines

DFT calculations were applied to investigate the relationship between the molecular structure and the Raman spectra of quinolines. A variety of different quinolines with increasing complexity was investigated and an aminoquinoline nucleus was found that describes the Raman spectrum of protonated chloroquine. It was discovered that the biological important, rigid C7-chloro group and C4-side chain of chloroquine significantly disturb certain molecular vibrations. The protonation at the N1 position causes dramatic changes of the Raman bands in the wavenumber region between 1500 cm−1 and 1650 cm−1. These bands are putative marker bands of the aminoquinoline drugs for π–π interactions to the hematin targets in malaria infected cells. The calculation of the normal modes and the illustration of the associated atomic displacements are very valuable for a deeper understanding of the associated bands in the Raman spectra.