Crystal structure of N-butyl-2,3-bis(dicyclohexylamino)cyclopropeniminium chloride benzene monosolvate

Abstract

N-Butyl-2,3-bis(dicyclohexylamino)cyclopropenimine (1) crystallizes from benzene and hexanes in the presence of HCl as a monobenzene solvate of the hydrochloride salt, [1H]Cl·C6H6 or C31H54N3+·Cl−·C6H6, in the P21/n space group. The protonation of 1 results in the generation of an aromatic structure based upon the delocalization of the cyclopropene double bond around the cyclopropene ring, giving three intermediate C—C bond lengths of ∼1.41 Å, and the delocalization of the imine-type C—N double bond, giving three intermediate C—N bond lengths of ∼1.32 Å. Ion–ion and ion–benzene packing interactions are described and illustrated.

Keywords

• crystal structure
• cyclopropene
• superbases
• aromaticity