When discussing aromatic heterocyclic rings, it is suggested that the bonds are all of equal length. However, research has found that the condensation reaction between a diketone and diamine results in asymmetric quinoxalines with differing bond lengths. To expand on prior research, potential quinoxaline bond length isomers were synthesized and analyzed. In the first approach, 4-methylcatechol and 9,10-diaminophenanthrene were combined with acetic acid and left to stir over the weekend. The crude product was recrystallized using methanol. In the second approach, 3,4-diaminotoluene and phenanthrenequinone were refluxed using acetic acid and recrystallized with toluene. Crystals will be synthesized and analyzed using X-ray diffraction. The bond lengths will be studied once enough information is retrieved from the diffraction process. With further research, it is expected that the N-C bonds formed from the diketone and the diamine will differ in length.

Synthesis of quinoxalines and the analysis of their bond lengths via x-ray diffraction

253rd National Meeting (2017)

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