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

Pessia Gilinsky-Sharon; Hugo E Gottlieb; David E Rajsfus; Keren Keinan-Adamsky; Vered Marks; Pinchas Aped; Aryeh A Frimer

doi:10.1002/mrc.3861

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

Magn Reson Chem. 2012 Oct;50(10):672-9. doi: 10.1002/mrc.3861. Epub 2012 Aug 24.

Authors

Pessia Gilinsky-Sharon¹, Hugo E Gottlieb, David E Rajsfus, Keren Keinan-Adamsky, Vered Marks, Pinchas Aped, Aryeh A Frimer

Affiliation

¹ The Ethel and David Resnick Chair in Active Oxygen Chemistry, Department of Chemistry, Bar-Ilan University, Ramat Gan, Israel.

PMID: 22926948
DOI: 10.1002/mrc.3861

Abstract

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 (13)C and (15)N NMR data, x-ray analysis and ab initio calculations, we suggest that the title compounds are always zwitterionic and that the C(A)-C(N) bond is not a true double bond.