Collect. Czech. Chem. Commun. 2009, 74, 323-333
Published online 2009-02-16 15:45:21

Preferential formation of homochiral silver(I) complexes upon coordination of two aza[6]helicene ligands to Ag+ ions

Jiří Míšek, Miloš Tichý, Irena G. Stará, Ivo Starý* and Detlef Schröder*

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


By means of selective deuterium labeling of 1-aza[6]helicene combined with resolution of the enantiomers, chiral discrimination in silver(I)-bound dimers of the type [LAgL′]+ is probed by electrospray mass spectrometry. The analysis of the results reveals a pronounced preference for the formation of homochiral dimers (P,P and M,M, respectively) over the statistically preferred heterochiral variant (P,M), which is fully consistent with previous data about the formation of homochiral dimers in the condensed phase. Further, competitive experiments with mixtures of 1- and 2-aza[6]helicene suggest a largely preferred coordination of 1-aza[6]helicene to the silver(I) cation.

Keywords: Fused pyridines; Helical heterocycles; Azahelicenes; Chiral discrimination; Mass spectrometry; Metal-bound dimers; Silver complexes.

References: 29 live references.