Heteroaryl nitrone spin traps have been suggested to act as free radical scavengers. The geometry optimizations and the single-point energies of the spin trapping reactions of the heteroaryl nitrones, 5,5-dimethylpyrroline-N-oxide (DMPO) and α-phenyl-N-t-butylnitrone (PBN) have been computationally studied using ab initio (Hartree-Fock (HF) and second-order Møller-Plesset (MP2)) methods and Density Functional Theory (DFT) methods. The effects of new heteroaryl substituents on a parent nitrone spin trap have been examined at the HF and MP2 levels with the 6-31G*, and cc-pVnZ (n=D, T, Q) basis sets. The thermodynamics of the spin trapping at the C-site and O-site with •H, •CH3 and •OH radicals were studied at the HF/6-31G* and DFT/m06/6-31G* levels. The addition reactions favor at the C-sites and the double adducts are thermodynamically more stable than the mono adducts. The spin trapping of DMPO, PBN and α(Z)-(3-methylfuroxan-4-yl)-N-tert-butylnitrone (FxBN) with •OH have also been studied.
| Identifer | oai:union.ndltd.org:ETSU/oai:dc.etsu.edu:etd-4463 |
| Date | 01 May 2016 |
| Creators | Asempa, Eyram |
| Publisher | Digital Commons @ East Tennessee State University |
| Source Sets | East Tennessee State University |
| Language | English |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Electronic Theses and Dissertations |
| Rights | Copyright by the authors. |
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