Theoretical AM1 studies of inclusion complexes of heptakis(2‐O‐hydroxypropyl)‐β‐cyclodextrins with alkylated phenols

Abstract

Semiempirical Austin model I (AM1) calculations have been performed on a family of inclusion complexes of heptakis(2-O-hydroxypropyl)-␤-cyclodextrin isomers derived from the 2-hydroxyl position (2HP␤CD) and from the 6-hydroxyl position (6HP␤CD) with alkylated phenol derivatives. From the stabilization energies and hydrogen bonding studies of the inclusion complexes of 2HP␤CD and 6HP␤CD with substituted phenols in head-first and tail-first positions, we found that the main driving forces for the formation of the inclusion complexes are from the van der Waals interactions.

Chiral recognition of Propranolol enantiomers by β-Cyclodextrin: Quantum chemical calculation and molecular dynamics simulation studies

“…Average deviations and standard deviations are also included. observations is consistent with the results of studies by Haung and co-worker [21], who found that the main driving forces for the formation of the inclusion complexes originate from the van der Waals interactions. It should be kept in mind that force field parameters used in the simulation ensemble of the complex are quantum-mechanical-based parameters.…”

“…They performed PM3 method on six inclusion complexes in search of correlation of migration order with their relative stability. Also, Huang and co-worker [21], have performed AM1 method on a family of inclusion complexes of heptakis(2-Ohydroxypropyl)-b-Cyclodextrin isomers. They found that the main driving forces for the formation of the inclusion complexes originate from the van der Waals interactions.…”

Investigation of the inclusion complex of tolfenamic acid with β-cyclodextrin: Geometry and NBO analysis

“…Molecular modelling is one of the most important methods to investigate the formation of cyclodextrin inclusion complexes [9][10][11][12][13][14][15][16][17][18][19][20][21][22]. This study is aimed to give information about the geometries and the driving forces of the formation of inclusion complex of TA and b-CD by semi empirical and ONIOM2 methods.…”

Computational modeling of inclusion complexes of β‐cyclodextrin with enantiomers of salsolinol, N‐methyl‐salsolinol, and 1‐benzyl‐tetrahydroisoquinoline

“…In recent years, various theoretical studies have been made on CD inclusion complexes with the aim of correlating the experimental results with the mode of the interaction between a CD host and a guest molecule 41–44. Although molecular mechanics (MM) and molecular dynamics (MD) with various force field approaches are increasingly being used in modern theoretical calculations, semiempirical methods such as AM1 (Austin Model 1)45 and PM3 (Parametric Method 3)46 are more commonly used for structure optimization of very large systems or for reactions involving large molecular systems 44, 47–53. It has been generally accepted that PM3 has high computational efficiency and permits the modeling of large systems beyond the capacity of ab initio methods 54.…”