Exploring the Relationship between Reactivity and Electronic Structure in Isorhodanine Derivatives Using Computer Simulations

The electronic structure and reactivity of 22 isorhodanine (IsRd) derivatives in the Diels-Alder reaction with dimethyl maleate (DMm) were investigated under two different environments (gas phase and continuous solvent CH3COOH), using free Gibbs activation energy, free Gibbs reaction energy, and frontier molecular orbitals to analyze their reactivity. The results revealed both inverse electronic demand (IED) and normal electronic demand (NED) characteristics in the Diels-Alder reaction and also provided insights into the aromaticity of the IsRd ring by employing HOMA values. Additionally, the electronic structure of the IsRd core was analyzed through topological examination of the electron density and electron localization function (ELF). Specifically, the study demonstrated that ELF was able to successfully capture chemical reactivity, highlighting the potential of this method to provide valuable insights into the electronic structure and reactivity of molecules.

Automated summary

The electronic structure and reactivity of 22 isorhodanine derivatives in the Diels-Alder reaction were studied under two different environments using various methods. The results showed both inverse electronic demand and normal electronic demand characteristics in the reaction and provided insights into the aromaticity of the isorhodanine ring. Additionally, the study demonstrated the potential of electron localization function analysis to capture chemical reactivity and provide valuable insights into the electronic structure of molecules.