Current Status of Quantum Chemical Studies of Cyclodextrin Host–Guest Complexes

Abstract

This article aims to review the application of various quantum chemical methods (semi-empirical, density functional theory (DFT), second order Møller–Plesset perturbation theory (MP2)) in the studies of cyclodextrin host–guest complexes. The details of applied approaches such as functionals, basis sets, dispersion corrections or solvent treatment methods are analyzed, pointing to the best possible options for such theoretical studies. Apart from reviewing the ways that the computations are usually performed, the reasons for such studies are presented and discussed. The successful applications of theoretical calculations are not limited to the determination of stable conformations but also include the prediction of thermodynamic properties as well as UV–Vis, IR, and NMR spectra. It has been shown that quantum chemical calculations, when applied to the studies of CD complexes, can provide results unobtainable by any other methods, both experimental and computational.

Unveiling the synergy: a combined experimental and theoretical study of β-cyclodextrin with melatonin

“…On the topic of CD inclusion complexes several computational works have been performed in the last few years. [37][38][39] Stachowicz et al studied the different conformations of b-CD in the gas phase at the B3LYP level, featuring the possible H-bond patterns generated by the hydroxymethyl groups of the different glucopyranose units. 40 To investigate the structures of the three most used CDs (a, b and g), some of us have recently applied the r 2 SCAN-3c composite functional obtaining a complete benchmark.…”

A Review of Applications of Solid-State Nuclear Magnetic Resonance (ssNMR) for the Analysis of Cyclodextrin-Including Systems

“…To achieve this goal, that is, to understand the structure and dynamics of the CD-based materials, multiple analytical and computational methods have been applied. The latter ones, including the quantum mechanics calculations [ 10 ] and molecular dynamics simulations [ 11 ], have been recently reviewed by us. From the experimental ones, likely the most commonly ones used in the analysis of CD-based materials in solid state are Fourier-transform infrared spectroscopy (FT-IR) and powder X-ray diffraction (PXRD), together with the thermo-analytical techniques, such as differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).…”

Influence of β-Cyclodextrin Methylation on Host-Guest Complex Stability: A Theoretical Study of Intra- and Intermolecular Interactions as Well as Host Dimer Formation

“…These inclusion complexes have been studied and extensively characterized by a range of analytical techniques [ 16 ]; however, decoupling their non-covalent interactions on a fundamental level is often difficult with experimental solution phase techniques, where all non-covalent interactions contribute simultaneously [ 17 ]. Interactions in CD inclusion complexes have been extensively modelled with computational techniques [ 18 ], predominantly with molecular dynamics simulations [ 19 ] and density functional theory (DFT) [ 20 ]. The latter was shown to be ideally suited to model the non-covalent interactions of CD complexes with a high level of accuracy [ 20 ], and recently a method to estimate the energies and nature of non-covalent interactions from the density of critical bonding points has been reported [ 21 ].…”

“…Interactions in CD inclusion complexes have been extensively modelled with computational techniques [ 18 ], predominantly with molecular dynamics simulations [ 19 ] and density functional theory (DFT) [ 20 ]. The latter was shown to be ideally suited to model the non-covalent interactions of CD complexes with a high level of accuracy [ 20 ], and recently a method to estimate the energies and nature of non-covalent interactions from the density of critical bonding points has been reported [ 21 ]. We suggest that this methodology can also be applied to CD-based host-guest complexes.…”