ANALYSIS OF PIPERIDINE DERIVATIVES USING METHODS QUANTUM CHEMISTRY
Keywords:
piperidine derivatives, HyperChem, reactivity, charge characteristics, thermodynamic stabilityAbstract
For research were taken models of 8 chemical compounds of piperidine derivatives, for which the spatial, electronic and energy characteristics were calculated using the HyperChem program using three semi-empirical methods AM1, PM3, RM1. The calculation of the energy characteristics of the model compounds of piperidine derivatives made it possible to establish their thermodynamic stability. Calculations of the charge characteristics of piperidine derivatives have shown that all compounds have one nucleophilic reaction center, which is oxygen in the benzoyl radical. Analysis of reactivity indices possible to determine the chemical stability of the compounds piperidine derivatives, depends directly on the magnitude of energy gap HOMO-LUMO; all studied model structures are nucleophiles and rigid in nature; prone to solubility in protophilic solvents.An analysis of the calculated enthalpies of formation of model molecules shows that two compounds are the most thermodynamically stable.
References
[1] Praliyev K.D. С- and N-substituted mono- and bicyclic piperidines: synthesis, stereochemistry, transformations and properties. New synthetic analgesics and anesthetics // Materials of the I Intern. conf. "Nitrogen heterocycles and alkaloids". M., 2001. Р. 130-138.
[2] Akhmetova G.S. Synthesis and structure of 1-(3-ethoxypropyl)-4-phenyl-4- hydroxypiperidine and some of its esters // Bulletin of the National academy of sciences of the Republic of Kazakhstan. 2010. N 4. P. 63-66.
[3] Yudin A.L. Laboratory workshop Quantum-chemical modeling of compounds in the HyperChem package: teaching aid. Kemerovo, 2013. 175 p.
[4] Semenov S.A. HyperChem Application Suite Quantum Mechanics: Textbook. M.: MITT them. Lomonosov, 2006. 30 p.
[5] Holtier H.–D. Molecular Modeling: Theory and Practice / H.-D. Hölthier, W. Zippl, D. Ronyan [et al.]. M.: Binom. Knowledge Laboratory, 2013.
[6] Kobzev G.I. The use of non-empirical and semi-empirical methods in quantum chemical calculations: a training manual. Orenburg: GOU OGU, 2004. 150 p.
[7] Forti F. Extension of the MST Continuum Solvation Model to the RM1 Semi-empirical Hamiltonian / F. Forti, X. Barril, F. J. Luque, M. Orozco // J. Comput. Chem. 2008. Vol. 29, N 4. Р. 87.
[8] Řezáč J. Advanced Corrections of Hydrogen Bonding and Dispersion for Semiempirical Quantum Mechanical Methods / J. Řezáč, P. Hobza // J. Chem. Theory Comput. 2012. Vol. 8, Issue 1. P. 141-151.
[9] Rocha G.B. RM1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I / G.B. Rocha, R.O. Freire, A.M. Simas, J.J.P. Stewart // J. Comp. Chem. 2006. Vol. 27, N 10. P. 1101–1111.
