The equilibrium constants (K) for the inclusion complexation of three kinds of β-cyclodextrins (β-CDs: native β-CD, heptakis(2,6-di-O- methyl)-β-CD, and 6-O-α-d-glucosyl-β-CD) with OH-substituted naphthalenes (2-naphthol, 2,3-dihydroxynaphthalene, and 2,6- dihydroxynaphthalene) were determined from the induced chemical shifts of NMR measurements for inclusion complexes: K = 188-1,250 mol-1 dm 3. The modified β-CDs form stable 1:1 inclusion complexes with OH-substituted naphthalenes, and the high stability of inclusion complexes of 2,6-dihydroxynaphthalene having a hydrophobic body and hydrophilic ends is shown. In addition, the structures of inclusion complexes were characterized by 2D ROESY NMR measurements. The differences in the structure of the inclusion complexes were observed for three kinds of naphthol guest molecules. Based on the results, the inclusion abilities enhanced by methylation of the OH groups at the CD rim or the side chain of branched β-CD are discussed.
|Number of pages||7|
|Journal||Journal of Inclusion Phenomena and Macrocyclic Chemistry|
|Publication status||Published - Jun 2009|
- Inclusion complex
ASJC Scopus subject areas
- Food Science
- Condensed Matter Physics