Location
Student Center
Document Type
Poster
Start Date
19-8-2025 2:30 PM
End Date
19-8-2025 3:30 PM
Description
Tröger’s base is a unique V-shaped, bicyclic, chiral molecule that has the flexibility to have derivatives added to its carbon backbone. This allows for Tröger’s base to be used in many material applications. This research focuses on the addition of a carbamoyl group(-CONEt2) to Tröger’s base that can form either an endo- or exo-isomeric form. The exo-derivative of Tröger’s base is shown to be the more stable species. Recent work has shown that the endo-derivative can be selectively produced by sequential proton transfer under highly-basic, cold conditions, through deprotonation followed by a protic quench. Prior research has predicted that this reaction proceeds through a charged enolate intermediate, but has not shown a clear mechanism for selectivity of the endo-product. This project focused on determining the impact of the THF solvent and the effect temperature has on both mechanistic steps using Density Functional Theory (DFT) calculations.
Included in
Determination of the Reaction Mechanism for the Tautomerization of Tröger’s Base
Student Center
Tröger’s base is a unique V-shaped, bicyclic, chiral molecule that has the flexibility to have derivatives added to its carbon backbone. This allows for Tröger’s base to be used in many material applications. This research focuses on the addition of a carbamoyl group(-CONEt2) to Tröger’s base that can form either an endo- or exo-isomeric form. The exo-derivative of Tröger’s base is shown to be the more stable species. Recent work has shown that the endo-derivative can be selectively produced by sequential proton transfer under highly-basic, cold conditions, through deprotonation followed by a protic quench. Prior research has predicted that this reaction proceeds through a charged enolate intermediate, but has not shown a clear mechanism for selectivity of the endo-product. This project focused on determining the impact of the THF solvent and the effect temperature has on both mechanistic steps using Density Functional Theory (DFT) calculations.