An NMR and X-ray study of the structure of the azo coupling product of 4-dimethylaminopent-3-en-2-one and benzenediazonium-tetrafluoroborate
Language English Country Great Britain, England Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
14527160
DOI
10.1039/b303206j
Knihovny.cz E-resources
- MeSH
- Borates MeSH
- Models, Chemical MeSH
- Diazonium Compounds chemistry MeSH
- Nitrogen chemistry MeSH
- Hydrazones chemistry MeSH
- Crystallography, X-Ray methods MeSH
- Boric Acids chemistry MeSH
- Magnetic Resonance Spectroscopy methods MeSH
- Models, Molecular MeSH
- Temperature MeSH
- Carbon chemistry MeSH
- Hydrogen chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- benzenediazonium MeSH Browser
- Borates MeSH
- Diazonium Compounds MeSH
- Nitrogen MeSH
- fluoroboric acid MeSH Browser
- Hydrazones MeSH
- Boric Acids MeSH
- phenylhydrazone MeSH Browser
- Carbon MeSH
- Hydrogen MeSH
4-Dimethylaminopent-3-en-2-one reacts with two molecules of benzenediazonium-tetrafluoroborate to give compound 1. The structure of this compound was determined by means of X-ray analysis of its crystal and 1H, 13C and 15N NMR spectra of its solution in CDCl3. The molecule of this compound contains one azo group and one hydrazone group. The substance exists, both in crystal form and in solutions of concentrations above 0.1 mol l(-1), in the form of a dimer, in which the pair of molecules are bound by two hydrogen bonds N-H...N. On diluting the solution, the dimers decompose, the two forms being in an equilibrium that is rapid on the NMR time scale.
References provided by Crossref.org
A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates
