Determination of the Fragmentation Pattern of Benzoquinones

Stephanie Heck* and Samuel David
Department of Chemistry, Shepherd University, Shepherdstown, WV 25443

Presentation Category: Science & Technology (Oral Presentation)

Student’s Major: Biochemistry

We are developing a new sophomore/advanced organic undergraduate laboratory experiment that enables students to self-discover mass spectral principles by operating the GCMS under varying conditions in order to discover and rationalize fragmentation mechanisms. We have chosen 2,6-dimenthylbenzoquinone as an example. Quinones are a class of compounds that are widespread in living systems and play a significant role in many important medicinal and biological processes. Benzoquinones follow specific fragmentation patterns as they fragment by sequentially losing a CO or C2H2 or other similar moieties. Since there are numerous patterns this could allow for, the aim is to establish the fragmentation pathway for 2,6-dimethylbenzoquinone utilizing tandem Mass Spectrometry (GCMS). For example, students will determine if fragmentation occurs via the m/z 80→m/z 52 → m/z 26 pathway, or via the m/z 80→m/z 54 → m/z 26 pathway. Other quinones will also be analysed. Results will be published in the Journal of Chemical Education.

Funding:

Program/mechanism supporting research/creative efforts: capstone course within my department