Author

Sejal Bhasin

Document Type

Honors Thesis

Date of Award

Fall 2023

Abstract

This study delves into analyzing the change in reaction enthalpy and activation energies of the Diels-Alder reaction for the synthesis of hydrogels, possessing diverse applications in scientific domains due to their unique properties. Utilizing the Diels-Alder reaction for hydrogel creation allows tailored structures responsive to specific stimuli. Theoretical calculations, employing computational methods, utilized the latest Spartan software (version 20) and conducting gas-phase calculations with semi-empirical methods (PM3) and Hartree-Fock (6-31G*). This research examines the hypothesis regarding the potential enhancement of reaction favorability through the introduction of an aromatic ring into the product, along with the incorporation of an electron-donating group as a substituent. The objective is to reduce the enthalpy gap, ultimately yielding a more stable product. The findings indicate that the inclusion of an aromatic ring coupled with an electron-donating groups on the reactants facilitates a more favorable reaction, further contributing to the reduction of the enthalpy gap. However, the extent of the substituent effect varies between the three reactions, showing a more pronounced impact in the anti-aromatic reactions, whereas in the reaction yielding an aromatic product, the aromatic structure itself emerges as the primary determinant driving the reaction.

Advisor

Allan Headley

Keywords

Diels-Alder reaction; hydrogels; enthalpy; activation energy; semi-empirical; Hartree-Fock

Included in

Chemistry Commons

Share

COinS