University Honors, Honors in Chemistry
Date of Award
Scott J. Kirkby
Thesis Professor Department
Frank B. Hagelberg
Free radicals are reactive molecules, which makes them difficult to study. Learning more about free radicals is necessary since they are implicated in many diseases and conditions such as Alzheimer’s disease and aging. Spin traps are molecules that can be used to stabilize free radicals to allow time for the free radicals to be characterized. The purpose of this research was to examine four novel spin traps that combine the properties of existing spin traps to possibly create more effective spin traps. The four novel molecules in question were designed by taking the 4-methylfuroxanyl ring from the α(Z)-(3-methylfuroxan-4-yl)-N-t-butylnitrone spin trap and combining it with the 5,5-dimethylpyrroline-N-oxide, the 5-methyl-,5-(trifluoromethyl)pyrroline-N-oxide, the 5-acetamide,5-methylpyrroline-N-oxide, and the 5-carboxamide,5-methylpyrroline-N-oxide spin traps. These four novel spin traps were studied using the hydroxyl radical since it is an abundant free radical in biological systems. The computational methods Hartree-Fock (HF) and Density Functional Theory (DFT) were used to calculate the optimized geometries for the reactant species and the hydroxyl radical additions at the C-site, at the O-site, and for the diadduct, which is when two free radicals add, at the HF/6-31G*, HF/cc-pVDZ, DFT/B3LYP/6-31G*, and DFT/B3LYP/cc-pVDZ levels of theory. From these calculations, the thermodynamic stability of the final product versus the initial reactants was obtained. The C-site addition was found to be more thermodynamically favorable for all the molecules than the O-site addition. The diadduct radical addition for the four molecules was the most thermodynamically favorable. The next step in the research would be to explore the methylfuroxan-4-yl ring on other molecules to continue expanding the effectiveness of spin traps, so free radicals can be better understood.
East Tennessee State University
Honors Thesis - Withheld
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This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
Harvey, Alexis, "Computational Study of Novel FxBN Spin Trap Analogs with Hydroxyl Radicals" (2020). Undergraduate Honors Theses. Paper 542. https://dc.etsu.edu/honors/542
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Available for download on Thursday, April 22, 2021