Determination of preferred conformations of ibuprofen in chloroform by 2D NOE spectroscopy.

Solution of an anti-inflammatory drug ibuprofen ((RS)-2-(4-isobutylphenyl) propionic acid) in chloroform was studied by nuclear magnetic resonance spectroscopy. A set of 2D NOESY spectra was analyzed in order to obtain atom-atom distances. Since ibuprofen is known to exist as an ensemble of different conformations, these distances are averaged over the ensemble. To compare experimental and calculated distances, three models of averaging were concerned. Our data allowed to determine the dominant conformers of ibuprofen dissolved in chloroform. The population of conformers in the saturated solution leads to a certain crystal morphology formed within the nucleation process. Observed and calculated (13)C chemical shifts (at the DFT/B3LYP/6-311+G(2d,p) level) were in good agreement.

Cyclodextrin-benzoic acid binding in salt solutions: effects of biologically relevant anions.

Inclusion complex formation of benzoic acid with α-, ß- and γ-cyclodextrins in water and in 0.2 M solutions of inorganic salts (KCl, KBr, KH2PO4 and K2SO4) has been studied by means of 1H NMR at 298.15 K. Binding constants have been determined and role of biologically active inorganic anions in the inclusion complex formation has been revealed. It has been shown that effects of the anions are determined not only by changing the ionic strength. More pronounced influence of Br- and H2PO4- compared with Cl- and SO4(2-) is caused by specific ion-molecular interactions, occurrence of which depends on the physical-chemical properties of the anions as well as on the binding mode of cyclodextrins with benzoic acid. Competing interactions of cyclodextrin-anion were observed in the presence of KBr, while the ternary complex formation was detected upon addition of KH2PO4.