ISSN:
1573-1111
Keywords:
Methylated cyclodextrin
;
inclusion complex
;
host-guest interaction
;
chiral recognition
;
crystal structure
;
Flurbiprofen
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Hepatakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TM-β-CDx) forms crystalline complexes with (R)-Flubiprofen (R-FP), C63H112O35C15H13O2F·H2O, and (S)-Flurbiprofen (S-FP), C63H112O35C15H13O2F. The crystal structures were determined by X-ray analysis. Crystals of both compounds are orthorhombic and the space group isP212121 with cell dimensions:a=15.092(2),b=21.714(3), andc=28.269(4) Å for theR-FP complex, anda=15.271(2),b=21.451(3) andc=27.895(3) Å for theS-FP complex. The macrocyclic ring of TM-β-CDx is markedly distorted because of the inability to form intramolecular hydrogen bonds and the steric hindrance involving methyl groups. In both complexes, the phenyl group is inserted into the host cavity from the O(2), O(3) side, which is wider than the O(6) side. The biphenyl moiety ofR-FP is fixed in theR-configuration within the host cavity. The phenyl group ofS-FP is disordered, andR-andS-configurations are statistically distributed with equal probability. TM-β-CDx molecules are stacked along theb axis to form a column structure. The TM-β-CDx molecule is laterally shifted with respect to the column axis, and a half of the guest molecule protrudes outside from the crevis of the column. The carboxyl group ofR-FP forms a hydrogen bond with water located outside the host cavity, while the carboxyl group ofS-FP is hydrogen-bonded to an oxygen atom of an adjacent TM-β-CDx.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00660743
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