Issue 20, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
14 Jan 2014
Accepted
21 Feb 2014
First published
21 Feb 2014

CrystEngComm, 2014,16, 4265-4273

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

N. Cheng, Q. Yan, S. Liu and D. Zhao, CrystEngComm, 2014, 16, 4265 DOI: 10.1039/C4CE00089G

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