J. Malone, C. M. Murray, G. Dolan
Dec 16, 1997
Citations
1
Influential Citations
40
Citations
Journal
Chemistry of Materials
Abstract
The synthesis, characterization, and crystal chemistry of N,N‘-diphenylisophthalamide (1) and pyridine-2,6-dicarboxylic acid bisphenylamide (2) are described. Through a combination of single-crystal X-ray diffraction and molecular orbital and crystal packing calculations, the important intermolecular interactions have been determined. The structures have been compared with the closely related structures, N,N‘-bis(3-hydroxyphenyl)isophthalamide (3) and N,N‘-dimethyl-N,N‘-diphenylisophthalamide (4). Crystalline 1 and 2 are isostructural, but there are subtle differences in the conformations and packing as a consequence of intramolecular hydrogen bonding in 2. This reduces the deviation from planarity in the molecular conformation of 2 and consequently lengthens the intermolecular hydrogen bonding distances. This is reflected in the lattice energies of 1 and 2 (−40.9 and −38.7 kcal/mol, respectively) and in the stacking energies of these compounds. For the compounds that do not contain an N atom in the centr...