Structures of inclusion complexes of halogenbenzoic acids and alpha-cyclodextrin based on AM1 calculations.
Semi-empirical quantum mechanics calculations using AM1 (Austin Method 1) were carried out for various host-guest combinations of alpha-cyclodextrin and mono-halogen benzoic acids. The energetically favorable inclusion structures were identified. The AM1 results show that alpha-cyclodextrin complexes with mono-halogen benzoic acid acids (where the halogen is chlorine, bromide, iodine) as guest compounds are more stable in the "head first" position than in the "tail-first" position for meta and para isomers while ortho mono-halogen benzoic acids complexes with alpha-cyclodextrin are more stable in "tail-first" position. The calculated structures were found to be in good agreement with those obtained from crystallographic databases.
Department of Chemistry, Autonomous University of Barcelona, Bellaterra, Spain. martin.pumera@uab.es
Martin
M
Pumera
Lubomír
L
Rulísek
D019817:Benzoic Acid / Q000737:chemistry*; D046911:Macromolecular Substances / Q000737:chemistry; D015394:Molecular Structure; D011789:Quantum Theory; D047391:alpha-Cyclodextrins / Q000737:chemistry*
D046911:Macromolecular Substances; D047391:alpha-Cyclodextrins; D019817:Benzoic Acid; C032613:alpha-cyclodextrin