The Chemistry of Powder and Explosives - Sciencemadness Dot Org

TETRACENE 447
its structure. It is formed by the action of nitrous acid on aminoguanidine,
or, more exactly, by the interaction of an aminoguanidine
salt with sodium nitrite in the absence of free mineral acid.
r\H0rNi0 P*-c >H H01-N0
H % "-' '^.. HI N NH-N^
Aminoguanldine Nitrous J Amlnoguanldine Nitrons
acid /
^C-NH-NH-N=N-Cf + 3H.0
NHJ
N NH-NH-NO
l-Guanyl-l-nltrosoamlnoguanyltetrazene
Tetracene is a colorless or pale yellow, fluffy material which is
practically insoluble in water, alcohol, ether, benzene, and carbon
tetrachloride. It has an apparent density of only 0.45, but yields
a pellet of density 1.05 when it is compressed under a pressure
of 3000 pounds per square inch. Tetracene forms explosive 1 salts,
among which the perchlorate is especially interesting. It is soluble
in strong hydrochloric acid; ether precipitates the hydrochloride
from the solution, and this on treatment with sodium acetate or
with ammonia gives tetracene again. With an excess of silver
nitrate it yields the double salt, C2H7N10OAg'AgNO3'3H2O.
Tetracene is only slightly hygroscopic. It is stable at ordinary
temperatures both wet and dry, but is decomposed by boiling
water with the evolution of 2N2 per molecule. On hydrolysis with
caustic soda it yields ammonia, cyanamide, and triazonitrosoaminoguanidine
which can be isolated in the form of a bright
blue precipitate of the explosive copper salt by the addition of
copper acetate to the alkaline solution. The copper salt on treatment
with acid yields tetrazolyl azide (5-azidotetrazole). 60
NH-C(NH)-NH-NH-N=N-C(NH)-NH-NH-NO
^ - N,-C^ +NH,+NH,-CN
X N
NH—NH—NO NH-N=N-OH
Triazonltrosoaminoguanldlne —
1— Cu-0 ,N—N
N-C; i > N3-C( ii
N X
NH-N=N
NH-N
Tetrazolyl azJde
60
Cf. survey article by G. B. L. Smith, "The Chemistry of Aminogutoidine
and Related Substances," Chem. Rev., 25, 214 (1939).