Browsing by Creator "Jump, Eric"
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Item A Comparison of Tropinone Derivative Synthesis Protocols in an Undergraduate Research Chemistry Course Laboratory(Northern Kentucky University) Jump, Eric"Heterocyclic compounds are ideal candidates for pharmaceutical compounds. They are used as mediums in the synthesis of anticancer medicines. I80- H37 is one such possible molecule created by direct heteroarylation via Palladium catalyst. I80-H37 is a heterocyclic compound featuring a tropinone scaffold with a single nitrogen group. Physiochemical properties were analyzed using Molinspiration and Percepta software to determine the compound's active drug potential. This study compares different methods for synthesizing I80-H37 to increase production efficiency and the potential efficacy of I80-H37 as a vehicle for anticancer drug delivery."Item Investigation on the Synthesis, Application and Structural Features of Heteroaryl 1,2-Diketones(2022-08-02) Wehrle, Robert J.; Rosen, Alexander; Nguyen, Thu Vu; Koons, Kalyn; Jump, Eric; Bullard, Mason; Wehrle, Natalie; Stockfish, Adam; Hare, Patrick M.; Atesin, Abdurrahman; Ateşin, Tülay A.; Ma, LiliA set of unsymmetrical heteroaryl 1,2-diketones were synthesized by a heteroarylation/oxidation sequence with up to 65% isolated yields. Palladium catalyst XPhos Pd G4 and SeO2 were the key reagents used in this methodology, and microwave irradiation was utilized to facilitate an efficient and ecofriendly process. The application of heteroaryl 1,2-diketones is demonstrated through the synthesis of an unsymmetrical 2-phenyl-3-(pyridin-3-yl)quinoxaline (5a) from 1-phenyl-2-(pyridin-3-yl)ethane-1,2-dione (4a). The lowest energy conformations of 4a and 5a were located using Density Functional Theory (DFT) at the M06-2X/def2-TZVP level of theory. Two lowest energy conformations of 4a differ with respect to the position of the N atom in the pyridyl ring and 0.27 kcal/mol energy difference between them corresponds to 60.4 and 39.6% at 50 °C in toluene. Four lowest energy conformations for 5a have the energy differences of 0.01, 0.03 and 0.07 kcal/mol that corresponds to 26.0, 25.7, 24.9 and 23.4%, respectively. A comparison of 4a and 5a to the less hindered analogs (oxalyl chloride and oxalic acid) is used to investigate the structural features and bonding using Natural Bond Orbital (NBO) analysis.