THERMODYNAMIC AND REACTIVITY ASPECT OF β-CYCLODEXTRINE INCLUSION COMPLEXES WITH COUMARIN DERIVATIVES

Abstract

In this study, the thermodynamic and reactivity characteristics of coumarin-derived ligand inclusion complexes with βCD were described, in addition to the in situ reactivity of these ligands and their changes in the complex cavity. For this purpose, computational tools such as molecular docking, second order perturbative analysis (E2PERT), ONIOM2 (DFT/PM6) methods were employed to obtain the global and local reactivity indices, and thermodynamic parameters, in addition to noncovalent interaction (NCI) analysis. As a result, it can be observed that the inclusion complexes are stable and viable given the ability to form non-covalent interactions, but their formation is not spontaneous under the modeling conditions. The global and local reactivity indices show that the ligands change their chemical reactivity inside the inclusion complex, demonstrating that the studied ligands present AOX SET activity outside the cavity, and HAT activity inside the cavity, mainly the C1 and C3 ligands.

A DFT-D4 investigation of the complexation phenomenon between pentachlorophenol and β-cyclodextrin

“…The enthalpy, entropy, and Gibbs free energy changes [51,52] of the complexation process of PCP with β-CD at standard temperature and pressure values (298.15 K and 1 atm) are reported in Table 2. The calculated ΔG° value is negative, showing that the complexation process is spontaneous.…”

ANTIOXIDANT CAPACITY OF CARBOLINE INCLUSION COMPLEXES WITH mβCD Y βCD

“…Given the arrangement of these sugars, a hydrophobic cavity and a hydrophilic external face are generated by the arrangement of hydroxyl groups [30,31]. This amphipathic characteristic of CDs makes them potential candidates for the transport and modification of physicochemical properties of molecules such as their reactivity [32], forming host-guest inclusion complexes [33]. The formation of inclusion complexes can be described by the thermodynamics of the process [34], which is mainly guided by Enthalpy (∆H), Entropy (∆S), Gibbs Free Energy (∆G) [35,36,37], and the stability of the inclusion complex, which can be described by the interaction energy (∆E int ) considering the Basis Set Superposition Error (BSSE), which is a phenomenon associated with the interaction and superposition of basis functions of interacting molecular systems [35,38,39].…”