Mechanistic and Catalytic Studies of Reversible Covalent Bonding

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With the support of the Chemical Structure, Dynamics, and Mechanism Program of the National Science Foundation, Professor Eric Anslyn of the University of Texas at Austin will lead a research program focused on dynamic covalent bonding. Four modern areas of chemistry are currently exploiting dynamic covalent bonding: supramolecular chemistry, Dynamic Combinatorial Chemistry (DCC), organocatalysis, and enzyme inhibition. However, the dynamic reactions routinely exploited in these areas are limited. This is due to the fact that most reactions involving reversible covalent bonding are very slow to equilibrate, and therefore exchange components on a time scale that is impractical. Our goal is to expand the number of reversible systems that are practical. To do this, the Anslyn team will first explore the mechanisms of four reversible covalent reactions, capitalize on successes that their group has recently had in this endeavor, and finally devise catalytic methods to speed up the reversible covalent interchange. The four reversible reactions they will target are: thiol conjugate addition, acetal formation, hemiaminal ether formation, and phosphinite transesterification. Understanding the mechanisms of these four reactions and uncovering methods for their catalysis will have a broad impact on the chemical community for two reasons. Firstly, they will create reversible covalent systems that other investigators can directly use for their own needs. Second, and maybe of even broader significance, they will demonstrate an approach for uncovering methods of catalysis that other chemists can also adopt for their goals. In addition to the scientific advances, the University of Texas (UT) at Austin offers a unique environment for broader impact. This University runs a Freshman Research Initiative (FRI) laboratory for undergraduates, wherein Dr. Anslyn always parallels a portion of this laboratory to complement his NSF funding. This laboratory is equipped and sponsored by UT, and thereby the NSF funding is leveraged to educate freshman chemistry students in a truly research oriented setting.