Abstract
Semiempirical AM1 calculations have been performed on the inclusion complexes of α- and β-cyclodextrin with benzoic acid and phenol and β-cyclodextrin with methylated benzoic acids in the “head first” and “tail first” positions. The results show that α-cyclodextrin complexes with phenol and benzoic acid guests in the “head first” position are more stable than in the “tail first” position, while β-cyclodextrin complexes with the same guests prefer the “tail first” position. The preferred orientation for β-cyclodextrin with methylated benzoic acids is determined by the position of the methyl substituent(s). In general, para-methyl benzoic acid derivatives prefer the “tail first” position. γ-cyclodextrin forms a slightly unstable 1:1 complex with C60 (3.4 kcal/mol), but two γ-cyclodextrins provide enough stabilization by about 10 kcal/mol to “cage-in” the C60.
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Bodor, N., Huang, MJ. & Watts, J.D. Theoretical am1 studies of inclusion complexes of α- and β-cyclodextrins with methylated benzoic acids and phenol, and γ-cyclodextrin with buckminsterfullerene. J Incl Phenom Macrocycl Chem 25, 97–102 (1996). https://doi.org/10.1007/BF01041545
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DOI: https://doi.org/10.1007/BF01041545