Date on Honors Thesis

Spring 4-29-2020


Chemistry, Polymer and Material Science



Examining Committee Member

Dr. Rachel Allenbaugh, Advisor

Examining Committee Member

Dr. Robert Johnson, Committee Member

Examining Committee Member

Dr. Kevin Miller, Committee Member


Mechanochemical synthesis, as used in this work, is the mechanical milling of reagents to drive reaction. It is often considered a greener alternative to traditional solution-based methods of synthesis. This work will describe the mechanochemical synthesis of furan-2-yl(pyrrolidin-1-yl)methanethione and N-hexadecylfuran-2-carbothioamide, the optimization of the mechanochemical synthesis of 1,3-dibenzylbenzimidazolium bromide as well as the kinetics of this reaction, and finally the ongoing development of the mechanochemical synthesis of N,N′-dioctyl-2,2′-bipyridine-4,4′-dicarboxamide.

This work studied both the traditional method and mechanochemical method for synthesis of furan-2-yl(pyrrolidin-1-yl)methanethione, as well as the mechanochemical method for N-hexadecylfuran-2-carbothioamide. While initial work was promising, it was found that decomposition occurred for both reactions, severely limiting conversion to product and skewing conversion calculations. The study of 1,3-dibenzylbenzimidazolium bromide was a continuation on previous work performed by the group. A full synthetic method was developed, as well as a high efficiency purification, giving 94.0% yield. Kinetics were studied by others in the group, and a summary is given in this work. The ongoing mechanochemical synthesis of N,N′-dioctyl-2,2′-bipyridine-4,4′-dicarboxamide builds upon liquid crystalline research by the group. Purification testing is still being developed, with different reaction methods being attempted to try and simplify refinement. A reaction method was developed that produced full conversion to product in 200 minutes of milling.

Creative Commons License

Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.