Ibuprofen (Ibu) and b-cyclodextrin (bCD) and its derivative (hydroxypropyl-b-cyclodextrin, HPbCD) complexes spatial geometry information were studyed. Firstly, phase solubility experiment was carried out for S-(+)-ibuprofen (SIbu) and cyclodextrins complex. The apparent stability constant (Kc) for 1:1 complexes are 1065 M-1 (bCD) and 1476 M-1 (HPbCD) respectively. Secondly, 1 H NMR and two-dimensional rotating-frame overhauser effect spectroscopy (2D ROESY) were used for binding study, and confirmed that benzene ring of Ibu is deeply included into the cavity and racemic Ibu (RSIbu) can be discriminated by bCD or HPbCD. Finally, docking model was given by theoretical investigation. The model with -4.77 kcal/mol binding energy matches experimental structure.