Conformational Study of Lidocaine and Bupivacaine by Quantum Mechanical Methods

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Rabani, Kosar | 2016

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Type of Document: M.Sc. Thesis
Language: Farsi
Document No: 51212 (04)
University: Sharif University of Technology
Department: Chemistry
Advisor(s): Tafazoli, Mohsen
Abstract:
In this thesis the structure and potential energy surfaces of Lidocaine and bupivacaine were studied by DFT method at B3LYD level calculation using 6-311++G basis set. Both compounds were calculated in water, dimetylsulfoxide, and carbontetracholoride as the solvent using the PCM model.Since the molecules meant to be studied were polar, level of energy in polar solvent is higher than non-polar solvent . The most considerable increase was observed in the amount of energy at 0.01 hartree for water compared with carbon tetracholoride. By changeing in solvent environment the most considerable difference in bond length was observed as 0.01 Ǻ.The spin spin coupling constants 1JCH, 2JCH, 2JHH, and 3JCH have been calculated by changing of α and β torsion angles. The effect of bond length on the 1J coupling constant was studied.The analysis of coupling constants in different solvents showed that the increase of solvent polarity, one-bond coupling constant increases while the vicinal and germinal coupling constants didn't change in different solvents. Also dependence of the coupling constant on the torsion angle, the karplus equation, is obtained by MATLAB softward
Keywords:
Density Functional Theory (DFT) ; Spin-Spin Coupling ; Quantum Computation ; Lidocaine ; Bupivacaine ; Curplus Equation