(2R,2′S)-2,2′-Bipiperidine-1,1′-diium dibromide

Abstract

The title compound, C10H22N22+·2Br−, was synthesized via reduction of 2,2′-dipyridyl with Ni–Al alloy/KOH, followed by separation of diastereoisomers (meso and rac) by recrystallization from ethanol. Although the two bridging C atoms are optically active, these two chiral centers adopt an (S,R) configuration; thus, the title compound contains an achiral meso form of 2,2′-bipiperidine. Both of the piperidinium rings adopt chair conformations, and the two N atoms are trans to each other; an inversion center is located in the mid-point of the central C—C bond. The conformation of the organic moiety resembles that of 1,1′-bi(cyclohexane). The organic diammonium cations are linked to each other through hydrogen bonding with bromide counter-ions, each of which forms two hydrogen bonds (N—H...Br) with two adjacent organic cations, thus linking the latter together in sheets parallel to (100).