Synthesis crystal structure, and DFT study of 3-benzyl-6-bromo-2-chloroquinoline and 3-benzyl-6-bromo-2-methoxyquinoline compounds

Abstract

3-Benzyl-6-bromo-2-chloroquinoline and 3-benzyl-6-bromo-2-methoxyquinoline are important intermediates for the synthesis of aryl quinoline compounds with quinoline ring. In this paper, the title compounds are obtained by four steps. The structures of the compounds are confirmed by FTIR, ¹H and ¹³C NMR spectroscopy, and mass spectrometry. At the same time, single crystals of the title compounds are measured by X-ray diffraction and subjected to crystallographic and conformational analyses. The molecular structures are further calculated using density functional theory (DFT), which were compared with the X-ray diffraction value. The results of the conformational analysis indicate that the molecular structures optimized by DFT are consistent with the crystal structures determined by single crystal X-ray diffraction. In addition, the molecular electrostatic potential and frontier molecular orbitals of the title compounds are further investigated by DFT, and some physicochemical properties of the compounds are revealed.

Keywords:

• 3-Benzyl-6-bromo-2-chloroquinoline
• DFT
• synthesis
• X-ray diffraction

Disclosure statement

The authors declare that they have no conflict of interests.

Additional information

Funding

This work was supported by the excellent youth project of Heilongjiang Natural Science Foundation (YQ2020H002), and the project of Cultivating Young Innovative Talents in Heilongjiang Province (UNPYSCT-2020056), and the Provincial Basic Scientific Research Operating Expenses Project of Heilongjiang Province (2018–KYYWF-0950). The theoretical calculations were conducted at the ScGrid and Deepcomp 7000 the Supercomputing Center, Computer Network Information Center of Chinese Academy of Sciences.