Nitrylamide

Structural formula
Mesomeric boundary structures
General
Surname	Nitrylamide
other names	Nitramine Nitramide Nitroamide
Molecular formula	H 2 N 2 O 2
Brief description	white solid
External identifiers / databases
CAS number 7782-94-7 PubChem 24534 Wikidata Q3082228
properties
Molar mass	62.03 g mol −1
Physical state	firmly
Melting point	72-75 ° C
safety instructions
GHS hazard labeling no classification available
Thermodynamic properties
ΔH f 0	−89.5 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nitrylamide is an inorganic chemical compound and the simplest member of the nitramine group . It is a structural isomer to hypositrous acid .

Extraction and presentation

Nitrylamide can be obtained through a multi-stage reaction starting from potassium cyanate with ethanolic hydrochloric acid , ethyl nitrate , ammonia , potassium hydroxide and sulfuric acid, the last step being the hydrolysis of dipotassium nitrocarbamate. It was first portrayed by J. Thiele and A. Lachman at the beginning of the 20th century.

${\displaystyle \mathrm {KOCN+HCl+C_{2}H_{5}OH\longrightarrow H_{2}NCOOC_{2}H_{5}+KCl} }$

${\displaystyle \mathrm {H_{2}NCOOC_{2}H_{5}+C_{2}H_{5}ONO_{2}+NH_{3}+H_{2}O\longrightarrow O_{2}NNH\cdot COONH_{4}} }$

${\displaystyle \mathrm {O_{2}NNH\cdot COONH_{4}+2\ KOH\longrightarrow O_{2}NNK-COOK+NH_{3}+2\ H_{2}O} }$

${\displaystyle \mathrm {O_{2}NNK\cdot COOK+2\ H_{2}SO_{4}\longrightarrow H_{2}NNO_{2}+CO_{2}+2\ KHSO_{4}} }$

It is also possible to display it by reacting nitrous oxide with ammonia

${\displaystyle \mathrm {N_{2}O_{5}+2\ NH_{3}\longrightarrow 2\ H_{2}NNO_{2}+H_{2}O} }$

or sodium sulfamate with nitric acid .

${\displaystyle \mathrm {NaSO_{3}NH_{2}+HNO_{3}\longrightarrow H_{2}NNO_{2}+NaHSO_{4}} }$

properties

Nitrylamide is a very decomposable solid that is in the form of shiny, white flakes. It is a very weak acid and soluble in ether, alcohol, water and acetone , sparingly soluble in benzene and hardly soluble in ligroin . It has a monoclinic crystal structure with the C 2 / c (No. 15) . It melts with partial decomposition, the solution being weakly acidic and decomposing at increasing speed into nitrous oxide and water. For example, the hydrolysis of nitramide is only catalyzed by bases but not by acids and is an example of general base catalysis. Johannes Nicolaus Brønsted formulated his acid-base concept based on investigations into the catalytic decomposition of nitramide . The compound decomposes explosively in the presence of caustic soda and on contact with concentrated sulfuric acid.

Individual evidence

1. ↑ ^{a b c d e f g} Georg Brauer (Ed.), With the collaboration of Marianne Baudler u. a .: Handbook of Preparative Inorganic Chemistry. 3rd, revised edition. Volume I, Ferdinand Enke, Stuttgart 1975, ISBN 3-432-02328-6 , p. 484.
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-13.
4. ^ ^{A b} A. F. Holleman , E. Wiberg , N. Wiberg : Textbook of Inorganic Chemistry . 101st edition. Walter de Gruyter, Berlin 1995, ISBN 3-11-012641-9 , p. 721.
5. ↑ ^{a b} Häussler, A .; Klapötke, TM ; Piotrowski, H .: Experimental and Theoretical Study on the Structure of Nitramide H ₂ NNO ₂ . In: Journal of Nature Research B . 55, 2000, pp. 151-156 ( online ).
6. ↑ Walter J. Moore: Fundamentals of physical chemistry . Walter de Gruyter, 1990, ISBN 3-11-009941-1 , p. 354 ( limited preview in Google Book search).
7. ↑ “The catalytic decomposition of nitramide and its physico-chemical significance,” in Zeitschrift fur physical chemistry, 108 (1924), 185–235
8. ↑ Lutz Roth, Ursula Weller-Schäferbarthold: Hazardous chemical reactions. 81. Supplementary delivery, ecomed-Verlag 2017.