Abstract
The interaction between eugenol and β-cyclodextrin in the presence of water is studied by molecular mechanics and dynamics simulations. A force field model is used in molecular mechanics to determine the interaction energy and the complex configuration at the absolute minimum. The van der Waals term is the main contribution to the total energy, and so directly determines the configuration of the inclusion complex. The formation of inclusion complexes is simulated by molecular dynamics, in which their configurations are deduced from the position probability density that represents the preferred location and orientation of the guest in the simulation. When eugenol approaches from the rims of β-cyclodextrin, it tends to enter the cavity, remain inside for a short period and then exit from it. The guest tends to include the phenyl ring inside the cavity in the most probable configurations. Two inclusion complex configurations are proposed, each with the hydroxyl and methoxyl groups pointing towards one different rim of β-cyclodextrin. The initial guest orientation is the main factor determining these configurations. The model presented in this study reproduces the experimental findings on inclusion complex formation and proposes two possible complex configurations, one previously suggested by different authors.
Highlights
Cyclodextrins (CDs) are macrocyclic molecules composed of glucose units forming truncated cone-shaped compounds
The aim of the present study is to theoretically examine the interaction between EG and β-CD in the presence of water, based on molecular mechanics (MM) and molecular dynamics (MD) simulations
The small amount of electrostatic energy is due to the presence of water, whose dielectric constant (ε) is 80, this contribution is similar for smaller values of ε
Summary
Cyclodextrins (CDs) are macrocyclic molecules composed of glucose units (six for α-CD, seven for β-CD, eight for γ-CD, etc.) forming truncated cone-shaped compounds. These give rise to cavities of different internal diameters, capable of containing molecules of different structure, size, and composition [1,2,3]. The ability of CDs and derivatized cyclodextrins to form inclusion complexes makes them useful in catalysis and chiral resolution of racemic compounds. Such processes are extensively employed in various research fields and technological applications. CDs and their inclusion complexes have been theoretically studied using several computational methods: molecular mechanics (MM) [8,9], molecular dynamics (MD) [6,10], and Monte Carlo simulations (MC) [11,12]
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