B12: Substituent Effects of Carbodiimide Fuel Reactivity

In biology, out-of-equilibrium, or “dissipative,” systems are crucial to functionality, using a constant supply of energy to continually function. We can mimic this behavior simply using chemical fuel reactions that result in the formation of a transient bond. Most other groups studying systems of this kind have used 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) as the fuel. Here, we attempt to investigate how adjusting the structure of a chemical fuel effects reactivity by synthesizing a variety of carbodiimides and comparing the rates of the reactions. We have successfully synthesized some of the carbodiimides and have identified the best conditions for running the experiments in the NMR spectrometer. Once the carbodiimides are pure and the experiments are run, we expect to show that different substituents either slow reactivity by sterically hindering the fuel or increase reactivity by stopping cyclization.

Author: Georgia Mantel

Advisor: Scott Hartley, Chemistry

Graduate Advisor: Renuka Baral, Chemistry

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