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

• Published in: Molecular Crystals and Liquid Crystals 2022-07, Vol.741 (1), p.114-123
• Main Authors: Zhou, S.-J., Feng, G.-X., Gong, Y.-X., Li, Q.-P., Yan, H., Geng, Y.-D.
• Format: Article
• Language: English
• Subjects: 3-Benzyl-6-bromo-2-chloroquinoline; Conformational analysis; Crystal structure; Crystallography; Crystals; Density functional theory; DFT; Mass spectrometry; Molecular orbitals; Molecular structure; NMR spectroscopy; Physicochemical properties; Quinoline; Single crystals; Synthesis; X-ray diffraction
• ISSN: 1542-1406; 1563-5287; 1527-1943
• DOI: 10.1080/15421406.2022.2081954

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, 1 H and 13 C 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.