Solid-state reactivity of the hydrazine-hydroquinone complex

The solid-state reactivities of the hydrazine–hydroquinone 1:1 complex and of hydrazine hydrochloride with solid aldehydes, ketones, carboxylic acids, thiohydantoin and 4-nitrophenyl isothiocyanate were investigated. Only the hydrazine complex provides quantitative additions, condensations, ring openings and ring closures. The solid-state mechanisms were investigated by atomic force microscopy (AFM) and the far-reaching anisotropic molecular movements are correlated with the crystal packing, both on the hydrazine complex surface and on the surface of two benzaldehydes. The hydrazine moves into the aldehyde crystals for chemical reaction without melting. Characteristic surface features are created by the common phase rebuilding and phase transformation on both the hydrazine-donating and -accepting crystals. Copyright © 2000 John Wiley & Sons, Ltd. Additional material for this paper is available from the epoc website at http://www.wiley.com/epoc