Intermolecular interactions in N-(ferrocenylmethyl)anthracene-9-carboxamide

Area of Science:

• Organometallic Chemistry
• Supramolecular Chemistry
• Crystallography

Background:

• Ferrocene derivatives are widely studied for their unique electronic and structural properties.
• Anthracene moieties are known for their photophysical characteristics and role in molecular assembly.
• Amide linkages are fundamental in organic chemistry and biological systems, facilitating molecular interactions.

Purpose of the Study:

• To synthesize and characterize a novel organometallic compound incorporating ferrocene and anthracene.
• To investigate the intermolecular interactions and crystal packing of the synthesized compound.
• To explore the structural consequences of coupling ferrocenylmethylamine with anthracene-9-carboxylic acid.

Main Methods:

• Synthesis via a coupling reaction between anthracene-9-carboxylic acid and ferrocenylmethylamine.
• Single-crystal X-ray diffraction analysis to determine the molecular structure and crystal packing.
• Analysis of non-covalent interactions, including hydrogen bonding and C-H.pi interactions.

Main Results:

• Successful synthesis of the title compound [Fe(C(5)H(5))(C(21)H(16)NO)].
• The ferrocenyl and anthracene groups are positioned nearly orthogonal to the central amide moiety.
• Principal intermolecular interactions include amide-amide hydrogen bonding, C-H.pi(arene) interactions, and C-H.O interactions, alongside short Fc-anthracene contacts.

Conclusions:

• The synthesized compound exhibits a well-defined structure with specific spatial arrangements of its functional groups.
• Intermolecular forces play a crucial role in the crystal packing and stability of this organometallic complex.
• The study provides insights into the supramolecular assembly of molecules containing both ferrocene and polycyclic aromatic hydrocarbon units.