𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part VII: Cyclodextrins with an inverse substitution pattern - synthesis and enantioselectivity

✍ Scribed by König, Wilfried A. ;Icheln, Detlef ;Runge, Torsten ;Pforr, Ingo ;Krebs, Adolf

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
475 KB
Volume
13
Category
Article
ISSN
0935-6304

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Transferring the site of specific substitution of dipentylated cyclodextrins with methyl or acyl residues from the secondary 3‐hydroxyl group to the primary 6‐hydroxyl group was expected to provide new information on the mechanism of chiral recognition. The 3‐position points towards and the 6‐position points away from the cyclodextrin cavity which via inclusion complex formation is supposed to play a major role in chiral separation. The “inverse” 6‐O‐acyl‐2,3‐di‐O‐pentyl‐cyclodextrins displayed almost no enantioselectivity but the corresponding 6‐O‐methyl derivatives are a versatile supplement to the chiral capillary GC phases nowadays available. Among the compounds that could be enantiomerically resolved are alcohols, amino acids, alkyl halides, bicyclic ethers, acetals, olefins, other hydrocarbons and chiral pharmaceuticals.

📜 SIMILAR VOLUMES

Cyclodextrins as chiral stationary phase
Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part VI: Octakis (2,3,6-tri-O-pentyl)-γ-cyclodextrin
✍ König, W. A. ;Kebber, R. ;Wenz, G. 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 English ⚖ 170 KB 👁 1 views

Perpentylated y-cyclodextrin is a very hydrophobic liquid which exhibits enantioselectivity toward a number of non-polar chiral substrates including the saturated hydrocarbons cisand transpinane, P-chiral olefins, iron(0) tricarbonyl complexes of prochiral olefins and 3,3,8,8-tetramethyl-trans-cyclo

Cyclodextrins as chiral stationary phase
Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part III: Hexakis(3-O-acetyl-2,6-di-O-pentyl)-α-cyclodextrin
✍ König, W. A. ;Lutz, S. ;Colberg, C. ;Schmidt, N. ;Wenz, G. ;von der Bey, E. ;Mos 📂 Article 📅 1988 🏛 John Wiley and Sons 🌐 English ⚖ 266 KB 👁 1 views

The properties of hexa kis(3-0-acetyl-2,6-di-O-pentyl)-a-cyclodextrin as a chiral stationary phase for capillary gas chromatography are described. For the first time the enantiomers of a series of different lactones are separated and their order of elution is assigned. Moreover, the enantiomers of t