1,1-Diamino-2,2-dinitroethylenes are always zwitterions

The nitration of tetraiodoethylene (7) yields 1,1-diiodo-2,2-dinitroethylene (8). The latter reacts with alkylamines 9 or alkyldiamines 11 to give the corresponding acyclic 1,1-diamino-2,2-dinitroethylenes 10 or their cyclic analogs 12, respectively. On the basis of liquid and solid-state 13C and 15N NMR data, x-ray analysis and ab initio calculations, we suggest that the title compounds are always zwitterionic and that the CACN bond is not a true double bond. Copyright (c) 2012 John Wiley & Sons, Ltd.