CHED 418 |
| Several phosphorthioamidates with different amino acid moieties were prepared and fully characterized using 31P NMR, 1H NMR, and IR spectroscopy. The synthesis process was governed by acid base chemistry and complex rearrangements, and involved reacting thiophosphoryl carbonyl mixed imides (synthesized by previous research students) with acid chlorides containing various amino acid functional groups. Phosphoryl thiocarbonyl mixed imides were formed upon rearrangement and examined kinetically using 31P NMR. These products were further cleaved, yielding thioamides, which were studied to determine bond rotational energies at various temperatures. The resonance forms of the thioamide impacts the bond rotation energies of interest (about the C—N bond), and NMR analysis detailed an increased rate in bond rotation at increased temperatures. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Chemical Education |