2021 Student Research Conference:
34th Annual Student Research Conference

Mechanistic Determination of Isomerization for Carbamoyl Derivatives of Tröger’s Base

Trey A. Maddaleno
Dr. Stuart G. Winikoff, Faculty Mentor

Derivatives of Tröger’s base (2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine) are valuable targets of study in catalysis, but their synthesis often produces the less desirable exo enantiomer in excess. Previous experimental study in Mizzou’s Harmata group has developed processes to modify Troger’s base with a number of substituents, particularly carbamoyl groups. Of particular interest is their development of an isomerization reaction between the endo and exo enantiomers using a diisopropylamine and n-butyllithium mixture with subsequent protic quenching. By modelling this reaction with density functional theory, the mechanism by which the reaction occurs can be verified, with this information lending to a better understanding of the molecules’ stereochemistry. Results indicate that steric forces associated with nitrogen substituents play a defining role in the reaction.

Keywords: DFT, computational chemistry, modelling


Presentation Type: Asynchronous Virtual Oral Presentation

Session: 6-10
Location: https://flipgrid.com/ebc10430
Time: 0:00

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