Synthesis and crystal structure of [(Sp)-(2-phenylferrocenyl)methyl]trimethylammonium iodide dichloromethane monosolvate

Abstract

As a follow-up to our research on the chemistry of disubstituted ferrocene derivatives, the synthesis and the structure of the title compound, [Fe(C5H5)(C15H19N)]I·CH2Cl2, is described. The cation molecule is built up from a ferrocene disubstituted by a trimethylammonium methyl group and a phenyl ring. The asymmetric unit contains the iodide to equilibrate the charge and a disordered dichloromethane solvate. The disordered model results from a roughly statistical exchange (0.6/0.4) between one Cl and one H. The packing of the structure is stabilized by weak C—H...X (X = I, Cl), C—H...π(Cp) and C—Cl...π(phenyl) interactions, building a three-dimensional network. The cation has planar chirality with Sp(Fc) absolute configuration. The structure of the title compound is compared with related disubstituted (trimethylammonio)methyl ferrocenes.

Keywords

• 1,2-disubstitued ferrocene
• planar chirality
• chiral ligands
• asymetric catalysis
• disordered dichloromethane
• crystal structure