Noncovalent interactions (NCIs) are the collection of both favorable and unfavorable interactions between molecules, such as hydrogen-bonding, ion-dipole, and π-π interactions. These interactions are at the core of asymmetric catalysis using chiral catalysts to convert an achiral or prochiral substrate to a chiral product. While these noncovalent interactions are minute in impact alone, collectively they ultimately dictate the fate and observed stereoselection of a reaction. Fortunately, they can be captured using density functional theory (DFT). A difference of only 2.7 kcal/mol can result in &gt;99% enantioselection in a reaction. In the lab, we have developed an enantioselective, organocatalyzed addition of a silyl-protected masked acyl cyanide (MAC) to various substituted beta-nitrostyrenes. This project involves the use of DFT calculations to be able to replicate this same enantioselection computationally using Gaussian16. With a computational model in hand, we can then probe the relevant NCIs, leading to the design of improved organocatalysts as well as extension to new bond forming processes.

Computational investigation of the organocatalyzed conjugate addition of a masked acyl cyanide to beta-nitrostyrene

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