Inclusion complexes of N-sulfamoyloxazolidinones with β-cyclodextrin: A molecular modeling approach

Abstract Host–guest interactions of a series of N-sulfamoyloxazolidinones with β-cyclodextrin have been investigated with molecular modeling, using PM3, PM6, ONIOM/2 methods, and NBO analysis. The complexes stabilities are influenced by the orientation and the nature of the substituted group in the phenyl of the guests. ONIOM/2 method was used to confirm the most favorable inclusion complex structure. The inclusion reaction in vacuum is exothermic and enthalpy driven process, while in water the inclusion is endothermic and enthalpy–entropy co-driven. NBO analysis demonstrates that the hydrogen bonds interactions are of type C - H ⋯ O with stabilization energies smaller than 2 kcal/mol indicating that the host–guest interactions are weak.