ORIGIN OF THE REACTIVITY OF TRIAZOLINEDIONES IN DIELS-ALDER REACTIONS FROM THE PERSPECTIVE OF INTERACTION-DISTORTION ANALYSIS

Project Details

Description

Triazolediones (TADs) are highly relevant molecules in Diels-Alder reactions as they can be applied in the synthesis, functionalization and analysis of polymers or biomolecules, presenting important advantages over conventional dienophiles. The versatility of TADs has meant that many experimental and some computational studies have been directed towards a better understanding of their properties and reactivity. However, current experimental studies have not yet achieved a higher level of molecular detail in the transformation of reactants to products and computational studies have only been limited to the evaluation of reaction energies or of frontier orbitals in the stationary states ( reactants, transition states, and products) without taking into account either the progress of the reaction or the distortion and interaction contributions of the fragments to the total energy. In this research, it is proposed to use a novel methodology that allows partitioning the total energy of the system into interaction energy and molecular distortion energy along the reaction coordinate. Additionally, the reactivity of the TADs will be evaluated by varying two important aspects in the reactions: the heteroatoms that form the double bond of the TADs and the substituents of the dienophile. Through this research, we hope to contribute with a rigorous analysis of TAD reactivity that complements the experimental and computational information that is currently available.

Objective

General: Determine the electronic and/or molecular factors causing the differences in reactivity of triazoledediones as dienophiles in Diels-Alder reactions using Interaction-Distortion Analysis within the framework of Density Functional Theory. Specific:- Establish a scale of reactivity of TADs in Diels-Alder reactions with different substitution patterns and anthracene as model diene.- Build a reactivity model for the studied reactions based on the interaction and distortion energies and energy decomposition analysis.

Expected results

This project aims to provide detailed knowledge at the electronic/molecular level of the Diels Alder reactions involving triazolinediones as dienophiles, through the variation of both the heteroatom in the structure of the dienophile and its substituents. This knowledge is necessary to optimize organic synthesis processes leading to obtain new biological and natural substances and polymeric materials, among others.
Short titleDiels-Alder
AcronymDiels-Alder
StatusFinished
Effective start/end date16/02/2121/05/22

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