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

Michal Michalski; Slawomir Berski

doi:10.3390/molecules28052360

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

Molecules. 2023 Mar 3;28(5):2360. doi: 10.3390/molecules28052360.

Authors

Michal Michalski¹, Slawomir Berski²

Affiliations

¹ Centre of New Technologies, University of Warsaw, 02-097 Warsaw, Poland.
² Faculty of Chemistry, University of Wroclaw, 50-383 Wroclaw, Poland.

Abstract

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.

Keywords: AIM; Diels-Alder; ELF; isorhodanine; reactivity.

Grants and funding

This research received no external funding.