Enhancing Reproducibility in Organic Chemistry and Analytical Data Comparisons

• Jacob Letnaunchyn, Chemistry, University of Delaware

• Donald Watson, Department of Chemistry and Biochemistry, University of Delaware
• Jessica Sampson, Department of Chemistry and Biochemistry, University of Delaware

There is no standard to achieve reproducibility and effective data comparisons (i.e. Analytical yields) in chemical research. “To what extent is reproducibility a significant issue in chemical research?” – Robert G. Bergman and Rick L. Danheiser. Bergman and Dangeiser discuss how reproducibility has always been a general issue in the field of chemistry. In this research, we are looking at two separate organic reactions (Ni-Catalyzed Suzuki Miyaura Coupling and Pd-Catalyzed Miyaura Borylation). Using these model reactions, we want to develop protocols to make sure that we can compare data collected at different sites by different researchers using multiple material handling techniques (i.e. manual and automated), in order to collect a more complete view of chemical reactivity. We are hoping to learn more about objective mechanisms through which we can compare literature. Findings in our research have built a platform for further exploration of the effect of reagent source, order of addition, and stir bar size on the yield of a reaction. Reactions were run on a microscale using manual high throughput experimentation techniques and analyzed by LC-MS for analytical yield vs. an internal standard and by relative area percent. We have seen in our research that base quality, reagent source, and stir bar size has an effect on the reaction yield of identical reaction plates. We have also seen that there is an apparent effect by the researcher on the reaction yields. Based on this research, we want to explore more variables, especially looking at specific reagent source effects (ArBr), stir bar effects, and using a heavier alcohol to prevent evaporation and leakage resulting in bad data comparison.