Self-Assembly of 1‑Deazahypoxanthine: Cooperativity of Hydrogen-Bonding and Stacking Interactions

A ladder-like
chain structure consisting of strong hydrogen bonds
was developed from 1-deazahypoxanthine. In addition, electrostatic
interactions derived from hydrogen-bond-induced π polarization
contribute synergistically with interchain stacking to form very strong
layered assemblies. Using structural data and difference Fourier diagrams
obtained from single-crystal X-ray structural analyses, it was revealed
that the quadrupole distribution of polarization charges on 1-deazahypoxanthine
favored strong intermolecular interactions.