Probing the intermolecular interactions of aromatic amides containing N-heterocycles and triptycene?

CrystEngComm Pub Date: 2014-02-21 DOI: 10.1039/C4CE00089G

Abstract

A series of aromatic amides incorporated with N-heterocycles or triptycene units are synthesized and studied for probing the effects of such chemical modifications on the intermolecular interactions. Single crystals of a number of heterocyclic amides and the triptycene-containing amide were obtained. Crystal structures, hydrogen bonds, lattice energy, solubility, and melting points were compared amongst relevant molecules. Suitably positioned nitrogen atoms from heterocycles are found to form intramolecular H-bonds with amide NHs at the expense of weakening or disrupting the intermolecular H-bonds. The effects of such H-bonding changes on solubility and melting point are nonetheless limited. Uniquely, the triptycene unit effectively improves the solubility of the amide without tempering the thermal resistance of the molecule.

Graphical abstract: Probing the intermolecular interactions of aromatic amides containing N-heterocycles and triptycene
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