Arrangement of Azidomethyl Group in Lupinine Azide: Structural and Spectroscopic Properties
Kopbalina K. Pankin D. Smirnov M. Ibrayev N. Turdybekov D.
February 2025Multidisciplinary Digital Publishing Institute (MDPI)
Molecules
2025#30Issue 3
Quinolizidine derivatives are an important class of substances that are used in the pharmaceutical industry. In previous studies, the synthesis of these substances is carried out using lupinine azide (IUPAC: 1-(azidomethyl)octahydro-2H-quinolizine), which is often used to obtain new biologically active compounds. In this regard, its structural characterization is critically important. In this work, the conformational diversity of the molecular structure of this compound has been studied. It is shown that the structure with the axial position of the methyl azide group contains a number of low-energy conformer states with energies higher than the ground state by 0.15–0.60 kcal/mol. Such structural ambiguity should manifest itself in the chemical reactions and biological activity of lupinine azide. The spectroscopic properties of the conformers were studied by modeling chemical shifts for carbon and hydrogen atoms, as well as by simulating IR absorption spectra. An analysis of the most specific spectroscopic features of all of the conformers was carried out. Based on the correlation of the theoretical results and the experimental spectroscopic data, a conclusion was made for the first time regarding the most probable conformational states in the solution.
azides , DFT , IR absorbance , lupinine , NMR , spectroscopy
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Department of Physics and Nanotechnology, Buketov Karaganda University, Universitetskaya 28, Karaganda, 100024, Kazakhstan
Center for Optical and Laser Materials Research, St. Petersburg State University, Ulianovskaya 5, St. Petersburg, 198504, Russian Federation
Faculty of Physics, St. Petersburg State University, Universitetskaya Nab. 7/9, St. Petersburg, 199034, Russian Federation
Institute of Molecular Nanophotonics, Buketov Karaganda University, Universitetskaya 28, Karaganda, 100024, Kazakhstan
Department of Physics, Abylkas Saginov Karaganda Technical University, Ave. Nazarbayev 56, Karaganda, 100027, Kazakhstan
Department of Physics and Nanotechnology
Center for Optical and Laser Materials Research
Faculty of Physics
Institute of Molecular Nanophotonics
Department of Physics
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