1,4-Bis{(+)-(S)-[1-(1-naphthyl)ethyl]iminomethyl}benzene

Abstract

The title compound, C 32 H 28 N 2 , is a chiral bis-imine in which both imine groups display the common E configuration. The naphthyl groups present different orientations with respect to the central core, as reflected in the dihedral angles of 21.4 (2) and 78.83 (14)° between the benzene and naphthyl mean planes, thus the highest possible C 2 local molecular symmetry is not attained. This C 1 mol­ecular conformation allows multiple C—H⋯π inter­molecular contacts involving all aromatic rings, while no π–π inter­actions are available for the stabilization of the crystal structure. The resulting packing structure is based on mol­ecules stacked along [100].

2,5-Bis{[(–)-(S)-1-(4-methylphenyl)ethyl]iminomethyl}thiophene

“…For the solvent-free approach in organic synthesis, see: Tanaka & Toda (2000). For the structure of a chiral bis-aldimine compound, see: Espinosa Leija et al (2009). For structures of thiophenes substituted in positions 2 and 5 by imine functionalities, see: Skene & Dufresne (2006); Fridman & Kaftory (2007); de Lima et al (2010); Kudyakova et al (2011Kudyakova et al ( , 2012.…”

“…In the last few years, our attention has been focused on the synthesis and structure of chiral bis-imines (e.g. Espinosa Leija et al, 2009), mostly due to their versatile coordination behavior and interesting properties as ligands for building of chiral metal complexes. Along this line, the title compound was synthesized through a Schiff condensation between a low-melting point dialdehyde and a liquid amine having a high boiling-point (above 200 °C), which also serves as a solvent for the reaction.…”