Synthesis, Characterization and Chemistry of the Fluoronitramide Anion

Jeffrey C. Bottaro; Richard Gilardi; Paul E. Penwell; Mark Petrie; Ripudaman Malhotra

doi:10.1055/s-2007-966004

SHORTPAPER

Synthesis, Characterization and Chemistry of the Fluoronitramide Anion

Jeffrey C. Bottaro*^,a, Richard Gilardi^b, Paul E. Penwell^a, Mark Petrie^a, Ripudaman Malhotra^a
^a Chemical Science and Technology Laboratory, SRI International, 333 Ravenswood Avenue, Menlo Park, CA 94025, USA
Fax: +1(650)8596196; e-Mail: ripudaman.malhotra@sri.com;
^b Naval Research Laboratory, Washington, DC 20375, USA

Abstract

All articles of this category

Abstract

The fluoronitramide anion, as its potassium, tetraisopropyl p-phenylenediguanidinium, and tetraphenylphosphonium salts, have been synthesized. The latter salt was characterized in detail as it was by far the most stable. The free acid HN(F)(NO₂) was found to be unstable, as was the ammonium salt of fluoronitramide. The fluorine atom was shown to be capable of displacement by nucleophiles. In contrast to dinitramide, which at room temperature is unreactive towards aqueous alkali, fluoronitramide reacts instantly with aqueous hydroxide. Single crystal X-ray diffraction data show an unusual degree of uncertainty in the position of the fluorine atom in all of the salts that were examined.

Key words

fluoronitramide - dinitramide - difluoramide - nitrocyanamide

Full Text

References

1 Schmitt RJ, Bottaro JC, Penwell PE, and Ross DS. inventors; US Patent 5198204.

2 Fokin AV. Kosyrev YM. Shevchenko VI. Russ. Chem. Bull. 1982, 31: 1626 ; Izv. Akad. Nauk SSSR, Ser. Khim. 1982, 1831

3 Boyer JH. Manimaran T. Wolford LT. J. Chem. Soc., Perkin Trans. 1 1988, 2137