Structural and spectral properties of quinolizidine alkaloids: quantum chemical calculations
Structural and spectroscopic properties of quinolizidine alkaloids lupinine and epilupinine stereoisomers were studied theoretically. The influence of the calculation method and structural change in the molecule on the results of geometry and other properties of compounds was considered. The equilibrium geometry, harmonic vibrational frequencies and infrared intensities were obtained by means of density functional theory (DFT/B3LYP) calculations with the split-valence medium-sized 6-31G(d) basis and Dunning’s correlation consistent basis set cc-pVDZ. From the optimized structure of the (+)-lupinine and (+)-epilupinine molecules, geometric parameters were compared with the literature X-ray experimental data. Structural and vibrational parameters for the (-)-lupinine and (-)-epilupinine molecules are predicted by theoretical calculations at B3LYP/6-31G(d) and B3LYP/cc-pVDZ levels of theory. Some physical characteristics for the title compounds, such as total electronic energy, zero-point energy, rotational constants and dipole moments were also defined by DFT methods. The thermodynamic functions of the title compounds were performed at the same theory levels. Stationary points are identified by the solution of the oscillatory problem.
2 Abduvahabov AA, Sadykov AS, Dalimov DN, Aslanov HA (1984) Alkaloids and their derivatives as a tool for studying the cholinergic system [Alkaloidy i ih proizvodnyie kak instrument dlya izucheniya holinergicheskoy sistemy]. FAN, Tashkent, Uzbekistan. (In Russian)
3 Tlegenov RT and Aitmambetov A (2005) Russ J Bioorg Chem+ 31:495-498. Crossref
4 Tlegenov RT (2007) Chemistry of Plant Materials [Khimija rastitel’nogo syr’ja] 4:69-72. (In Russian)
5 Michael JP (2016) Simple indolizidine and quinolizidine alkaloids in The Alkaloids, Chemistry and Biology (H.-J. Knölker, ed.). Academic Press, London, UK. Crossref
6 Winterfeld K, Holschneider FW (1931) Chem Ber 64:137-150. Crossref
7 Clemo GR, Rudinger J (1951) J Chem Soc 0:2714-2718. Crossref
8 Mnjoyan AL, Mnatsakanian VA, Harutyunian LS, and Muradian MS (1971) Chemical Journal of Armenia [Armyanskiy himicheskiy zhurnal] 24:271-276. (In Russian)
9 Mnatsakanian VH, Harutyunian LS, Alexanian RA, and Marashian ES (1972) Chemical Journal of Armenia [Armyanskiy himicheskiy zhurnal] 25:66-72. (In Russian)
10 Kasimov TK (1971) Synthesis and study of some derivatives of lupinine [Sintez i issledovanie nekotoryih proizvodnyih lupinina]. Thesis synopsis [Avtoref. dis. … kand. him. nauk]. Tashkent, Uzbekistan. (In Russian)
11 Nasipuri D (2011) Stereochemistry of organic compounds: Principles and applications. New Age International (P) Ltd. Publishers, New-Delhi, India. ISBN-13: 978-8122430295
12 Thomas AF, Vipond HJ, Marion L (1955) Can J Chem 33:1290-1294. Crossref
13 Koziol A, Kosturkiewicz Z and Podkowinska H (1978) Acta Cryst B34:3491-3494. Crossref
14 Koziol AE, Gdaniec M and Kosturkiewicz Z (1980) Acta Cryst B36:982-983. Crossref
15 Jahn MK, Dewald D, Vallejo-Lopez M, Cocinero EJ, Lesarri A, and Grabow JU (2013) J Phys Chem A 117:13673-13679. Crossref
16 Frisch MJ, Trucks GW, Schlegel HB et al. (2009) GAUSSIAN 09, Revision A.02. Wallingford CT.
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