Source:http://linkedlifedata.com/resource/pubmed/id/11818658
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
Pt 1
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| pubmed:dateCreated |
2002-1-30
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| pubmed:abstractText |
The NNO2 group of the title compound is significantly less twisted with respect to the aromatic ring in comparison to a typical secondary nitramine. The amide nitrogen is trigonally hybridized. The nitramino group is almost planar. The C-C-N-N torsion angles vary between ca 13 and 42 degrees, whereas the twist along the N-N bond is much smaller and amounts to between ca 1 and 15 degrees. Those twist angles are governed by a crystal packing and are much larger in the case of crystals of pure N,4-dinitroaniline in comparison to that of its complex with sulfolane. The deviations of the internal angles of the aromatic ring from 120 degrees do not exceed 3 degrees. The presence of the nitro group increases the C-C-C valence angle of ca 2.0-2.6 degrees, whereas an analogous effect associated with the nitramino group is much smaller (ca 0.3-1.3 degrees), pointing to its weak electron-withdrawing properties. The nitramino group displays no tendency to conjugate with an electron-demanding substituent across the ring. It participates in hydrogen bonding only as a hydrogen-bonding donor. It does not act as a proton acceptor, despite the fact that nitramine rearrangement is catalysed by acids.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Feb
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| pubmed:issn |
0108-7681
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:volume |
58
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
109-15
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| pubmed:dateRevised |
2007-7-24
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| pubmed:year |
2002
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| pubmed:articleTitle |
Structure of N,4-dinitroaniline and its complex with sulfolane at 85 K; on the proton donor-acceptor affinity of the primary nitramine (HNNO2) group.
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| pubmed:affiliation |
Institute of Chemistry, University of Opole, ul. Oleska 4845-052 Opole, Poland. zaleski@uni.opole.pl
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| pubmed:publicationType |
Journal Article
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