Article
Why 2,6-di-methyl-β-cyclodextrin can encapsulate OH-substituted naphthalenes better than β-cyclodextrin: binding pose, non-covalent interaction and solvent effect
Computational and Theoretical Chemistry
(2021)
Abstract
Naphthalenes, a class of persistent organic pollutants, are difficult to remove from environment due to their low water solubility. β-cyclodextrin (β-CD) and its derivatives can encapsulate these compounds and enhance their solubility. For OH-substituted naphthalenes, several inclusion complexes with β-CD and 2,6-di-methyl-β-CD (DMCD) of varying stabilities were reported. However, the role of non-covalent interaction was not defined and the binding mechanisms remain vague. We use a molecular dynamics/quantum mechanics/continuum solvent model to explore the inclusion mechanisms of these systems. Both the measured binding modes and binding trend are well reproduced by our computations. The host-guest non-covalent interaction favors the β-CD complexes, while the hydrophobic interaction favors the DMCD complexes, and the latter plays a more important role in determining the binding trend. A correlation between the polarizability of the inclusion complex as measured by its dipole moment and hydrophobic interaction is also revealed.
Keywords
- Naphthalene,
- 2,
- 6-di-methyl-β-cyclodextrin,
- Host–guest binding affinity,
- Dipole moment,
- Hydrophobic interaction,
- Non-covalent interaction
Disciplines
Publication Date
December, 2021
DOI
10.1016/j.comptc.2021.113496
Citation Information
Ke Chen, Renlong Ye, Xiao Liu, Chung Wong, et al.. "Why 2,6-di-methyl-β-cyclodextrin can encapsulate OH-substituted naphthalenes better than β-cyclodextrin: binding pose, non-covalent interaction and solvent effect" Computational and Theoretical Chemistry Vol. 1206 (2021) Available at: http://works.bepress.com/chung-wong/83/