Induced Circular Dichroism of β-Cyclodextrin Complexes with Substituted Benzenes

The induced circular dichroism (ICD) of β-Cyclodextrin(β-CDx)-substituted benzene complexes was investigated. We observed the ICD on the absorption bands of achiral substituted benzene molecules, which is considered to be induced by the dissymmetric field of the chiral β-CDx host molecule. The electronic transitions which are polarized along the long axis of the substituted benzenes showed positive ICD, while the sings of the ICD of short-axis polarized transitions are negative. The rotational strengths of these inclusion complexes were calculated by the Kirkwood-Tinoco expression. From the comparison between the experimental and calculated results, it is concluded that these β-CDx complexes favor the axial inclusion in which the long axis of the substituted benzenes is parallel to the axis of the β-CDx cavity.

[1]  M. Hatano,et al.  Magnetic circular dichroism studies on o-, m-, and p-nitroanilines and o-, m-, and p-aminobenzoic acids. , 1976 .

[2]  B. Hingerty,et al.  Topography of cyclodextrin inclusion complexes. 8. Crystal and molecular structure of the .alpha.-cyclodextrin-methanol-pentahydrate complex. Disorder in a hydrophobic cage , 1976 .

[3]  W. Saenger,et al.  Topography of cyclodextrin inclusion complexes. VI. The crystal and molecular structure of α-cyclodextrin-p-iodoaniline trihydrate , 1976 .

[4]  M. Hatano,et al.  Observed and calculated Faraday B terms in monosubstituted benzenes , 1976 .

[5]  B. Hingerty,et al.  Disorder in a hydrophobic cage illustrated by X-ray structure of α-cyclodextrin · methanol pentahydrate adduct , 1975, Nature.

[6]  A. Rassat,et al.  Nitroxides. LXX. Electron spin resonance study of cyclodextrin inclusion compounds , 1975 .

[7]  E. Kaiser,et al.  Studies on the interactions of spin-labeled substrates with chymotrypsin and with cycloamyloses. , 1975, Journal of the American Chemical Society.

[8]  K. Harata,et al.  The Circular Dichroism Spectra of the β-Cyclodextrin Complex with Naphthalene Derivatives , 1975 .

[9]  D. MacNicol Cyclodextrins as NMR shift reagents for hydrocarbons , 1975 .

[10]  S. Takenaka,et al.  Induced circular dichroism of benzoylbenzoic acids in β-cyclodextrin , 1974 .

[11]  Y. Matsui,et al.  Effects of Inorganic Salts on the Dissociation of a Complex of β-Cyclodextrin with an Azo Dye in an Aqueous Solution , 1973 .

[12]  W. Saenger,et al.  Water Molecule in Hydrophobic Surroundings: Structure of α-Cyclodextrin-Hexahydrate (C6H10O5)6·6H2O , 1972, Nature.

[13]  R. Bock,et al.  The interaction of cyclodextrins with nucleic acids. A study of secondary structure in three transfer ribonucleic acids. , 1970, Biochemistry.

[14]  W. Saenger,et al.  Inclusion Compounds. XIX.1a The Formation of Inclusion Compounds of α-Cyclodextrin in Aqueous Solutions. Thermodynamics and Kinetics , 1967 .

[15]  Donald E. Williams,et al.  The Crystal and Molecular Structure of the Cyclohexaamylose-Potassium Acetate Complex1 , 1965 .

[16]  H. Davis,et al.  Carbon-14 Tracer Study of the High Temperature Oxidation of Propylene , 1965 .

[17]  Joel H. Hildebrand,et al.  A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons , 1949 .