Synthesis 2007(8): 1151-1153  
DOI: 10.1055/s-2007-966004
© Georg Thieme Verlag Stuttgart · New York

Synthesis, Characterization and Chemistry of the Fluoronitramide Anion

Jeffrey C. Bottaro*,a, Richard Gilardib, Paul E. Penwella, Mark Petriea, Ripudaman Malhotraa
a Chemical Science and Technology Laboratory, SRI International, 333 Ravenswood Avenue, Menlo Park, CA 94025, USA
Fax: +1(650)8596196; e-Mail:;
b Naval Research Laboratory, Washington, DC 20375, USA
Further Information

Publication History

Received 20 December 2006
Publication Date:
28 March 2007 (online)


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.


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