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1,1‐Diamino‐2,2‐dinitroethylenes are always zwitterions
Author(s) -
GilinskySharon Pessia,
Gottlieb Hugo E.,
Rajsfus David E.,
KeinanAdamsky Keren,
Marks Vered,
Aped Pinchas,
Frimer Aryeh A.
Publication year - 2012
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.3861
Subject(s) - chemistry , nitration , ab initio , computational chemistry , solid state , stereochemistry , medicinal chemistry , organic chemistry
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. Copyright © 2012 John Wiley & Sons, Ltd.
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