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- Title
Polynitroethyl- and Fluorodinitroethyl Substituted Boron Esters.
- Authors
Klapötke, Thomas M.; Krumm, Burkhard; Moll, Richard
- Abstract
The reaction of boron oxide with various nitro-substituted ethanols (2-nitroethanol, 2-fluoro-2,2-dinitroethanol, 2,2,2-trinitroethanol) furnished the corresponding nitroethyl borates B(OCH2CH2NO2)3 ( 1), B(OCH2CF(NO2)2)3 ( 2), and B(OCH2C(NO2)3)3 ( 3). Fluorination of the anion [(NO2)2CCH2OH]− ( 4) resulted in 2-fluoro-2,2-dinitroethanol ( 5), a precursor for 2, and was thoroughly characterized. An interesting condensation was observed with the anion 4 to form the unusual dianion [(NO2)2CCH2C(NO2)2]2− ( 6). All compounds were fully characterized by multinuclear NMR spectroscopy, vibrational spectroscopy (IR, Raman), mass spectrometry and elemental analysis. The chemical, physical and energetic properties of 1- 3 and 5 are reported, as well as quantum chemical calculations at the CBS-4M level of theory to predict the enthalpies and energies of formation. X-ray diffraction studies were performed, and the crystal structures for compounds 1- 6 were determined and discussed thoroughly. The boron esters 1- 3 are of interest as possible candidates for smoke-free, green colorants in pyrotechnic applications, and in case of 2 and 3 also as promising high energy oxidizers.
- Subjects
BORON; ESTERS; BORON oxide; ETHANOL; FLUORINATION; NUCLEAR magnetic resonance spectroscopy; X-ray diffraction
- Publication
Chemistry - A European Journal, 2013, Vol 19, Issue 36, p12113
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201300964