Mechanochemical synthesis of N-salicylideneaniline: Thermosalient effect of polymorphic crystals

Abstract

Polymorphs of the dichloro derivative of N-salicylideneaniline exhibit mechanical responses such as jumping (Forms I and III) and exploding (Form II) in its three polymorphs. The molecules are connected via the amide N-H⋯O dimer synthon and C-Cl⋯O halogen bond in the three crystal structures. A fourth high-Temperature Form IV was confirmed by variable-Temperature single-crystal X-ray diffraction at 180°C. The behaviour of jumping exhibited by the polymorphic crystals of Forms I and III is due to the layered sheet morphology and the transmission of thermal stress in a single direction, compared with the corrugated sheet structure of Form II such that heat dissipation is more isotropic causing blasting. The role of weak C-Cl⋯O interactions in the thermal response of molecular crystals is discussed.