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Helicity discrimination in N,N'-dibenzoyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthrolines and their thiono- and selenocarbonyl analogues by inclusion complexation with chiral diols
Abstract
X-ray crystallographic analysis of the title compounds revealed that they assume a folded helical con- formation of an approximate C2 symmetry in the solid state. Dithioamide, diselenoamide and monoselenoamide were resolved to enantiomers by inclusion crystallization with optically active diols (TADDOLs). The absolute configuration of the guest molecules in the complexes was assigned as P. The optical activity of the resolved compounds is manifested by their CD spectra showing relatively strong Cotton effects in the region of thionoamide and selenoamide n-pi* transition. The optically active thiono- and selenoamides are configurationally labile compounds and gradually racemize in solution but they are stable in the form of the inclusion complexes. The first-order kinetics of the racemization in solution allowed us to assign the racemization barriers by the spectropolarimetric measurements
Authors (4)
-
Artur Sikorski
- Faculty of Chemistry, University of Gdansk ..
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
ORGANIC & BIOMOLECULAR CHEMISTRY
no. 11,
edition 43,
pages 7522 - 7529,
ISSN: 1477-0520 - Language:
- English
- Publication year:
- 2013
- Bibliographic description:
- Olszewska T., Sikorski A., Herman A., Połoński T.: Helicity discrimination in N,N'-dibenzoyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthrolines and their thiono- and selenocarbonyl analogues by inclusion complexation with chiral diols// ORGANIC & BIOMOLECULAR CHEMISTRY. -Vol. 11, iss. 43 (2013), s.7522-7529
- Verified by:
- Gdańsk University of Technology
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