Single-crystal X-ray studies of four representatives of "pushpull" proton sponges, namely 1,8-bis(dimethylamino)-, 1,8-bis(diethylamino)-, 1,8-bis(dipropylamino)-4,5-dinitronaphthalenes and 4,5-bis(dimethylamino)naphthalene-1,8-dicarbaldehyde have been performed at low and ambient temperatures. The most interesting and unexpected result is that the formyl groups in the peri-dialdehyde display stronger π-acceptor effects than the nitro groups. This phenomenon is ascribed to smaller steric demands of the CHO groups, their lower electrostatic repulsion, and specific packing forces.
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