Evaluation of (Z)-5-(Azulen-1-ylmethylene)-2-thioxothiazolidin-4-ones Properties Using Quantum Mechanical Calculations

Abstract

Derivatives of (Z)-5-(azulen-1-ylmethylene)-2-thioxothiazolidin-4-one are reported as heavy metal (HM) ligands in heterogeneous systems based on chemically modified electrodes. Their ability to coordinate HMs ions has recently been shown to be very selective. In this context, an additional computer-assisted study of their structure was performed using density functional theory (DFT) to achieve a complex structural analysis. Specific molecular descriptors and properties related to their reactivity and electrochemical behaviour were calculated. The correlation between certain quantum parameters associated with the general chemical reactivity and the complexing properties of the modified electrodes based on these ligands was carried out to facilitate the design of molecular sensors. Good linear correlations between DFT-calculated HOMO/LUMO energies and experimental redox potentials were found. A good agreement between the chemical shifts predicted by the DFT method and those determined experimentally from NMR data for these ligands demonstrated the accuracy of the calculations to assess the structural data. Such a computational approach can be used to evaluate other properties, such as electrochemical properties for similar azulene derivatives.

Keywords

• (Z)-5-(azulen-1-ylmethylene)-2-thioxothiazolidin-4-one derivatives
• quantum mechanical calculations
• molecular and QSAR properties
• reactivity parameters
• electrochemical properties