Jump to main content
Jump to site search

Issue 43, 2013
Previous Article Next Article

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

Author affiliations

Abstract

X-ray crystallographic analysis of the title compounds revealed that they assume a folded helical conformation of an approximate C2 symmetry in the solid state. Dithioamide 5b, diselenoamide 5c and monoselenoamide 5d were resolved to enantiomers by inclusion crystallization with optically active diols (TADDOLs). The absolute configuration of the guest molecules in the complexes 5b·6a, 5c·6a and 5d·6a 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–π* 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.

Graphical abstract: 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

Back to tab navigation

Supplementary files

Publication details

The article was received on 12 Jun 2013, accepted on 10 Sep 2013 and first published on 13 Sep 2013


Article type: Paper
DOI: 10.1039/C3OB41216D
Citation: Org. Biomol. Chem., 2013,11, 7522-7529

  •   Request permissions

    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

    T. Olszewska, A. Sikorski, A. Herman and T. Połoński, Org. Biomol. Chem., 2013, 11, 7522
    DOI: 10.1039/C3OB41216D

Search articles by author

Spotlight

Advertisements