Diazoverbindungen aus Amidoguanidin, Beiträge zur Kenntnis der Diazohydrazoverbindungen (Tetrazene)

Abstract

H o c k und Rudolf Roth: Diazoverbindungen auB Amidoguanidin, Beitrirge zur Kenntnis 'der Diazohydrazoverbindungen (Tetrasene). [Mittcil. aus den1 Chem. Labornt. d. KgI. Akad. (1. Wissenscli. zu Mfinchcn.) (Eingegmgen am 9. April 1910.) K. A. I I o f m a n n und R u d o l f R o t h ') haben kurzlich mitgeteilt; daB A m i d o g u a n i d i n n i t r a t mit N a t r i u m n i t r i t ohne Slurezusntz i n der Kiilte das farblose, scbiin krystallisierte Diazohydronyd, C2NloH7. OH, liefert, aus dem durch konzentrierte Siiuren farblose, leicht hydrvlysierbare Salze, CzNlaHi .S, entstehen, unter denen sirh besonders das Perchlorat, C~N I O H~.

Tetrazene–Characterization of Its Polymorphs

“…In addition, tetrazene can be dissolved in acids to form the corresponding salts, from which the starting material can be obtained by hydrolysis with quantitative yields [ 19 , 20 ]. Tetrazene recovered this way gives a predominantly C form-containing product with minor A content regardless of the starting salt or tetrazene form.…”

Remarks on the Evolution of Explosives

“…Tetrazene was synthesized for the first time in 1910 by Karl Andreas HOFMANN, Heinrich HOCK and Rudolf ROTH [10], by exposing the salt of aminoguanidine to a sodium nitrite solution. In 1921, Hans RATHSBURG investigated whether tetrazene could be used as detonating agent and sensitizer.…”

Investigation of Intramolecular Interactions in the Crystals of Tetrazene Explosive and Its Salts

“…As there was a certain misattribution regarding the discovery, the view of the chemical structure of tetrazene has changed over eight decades. At the beginning, Hofmann and Roth tentatively named this compound “Amidoguanidin-diazohydroxyd” and proposed its structures as “Guanyl-diazoguanyl-tetrazen” (Figure , I) and/or “Guanyl-nitrosoamidoguanyl-tetrazen” (Figure , II) . The structures were elucidated on the basis of elemental analysis and degradation reaction studies .…”

“…At the beginning, Hofmann and Roth tentatively named this compound “Amidoguanidin-diazohydroxyd” and proposed its structures as “Guanyl-diazoguanyl-tetrazen” (Figure , I) and/or “Guanyl-nitrosoamidoguanyl-tetrazen” (Figure , II) . The structures were elucidated on the basis of elemental analysis and degradation reaction studies . The azo group in these structures was confirmed by dye-producing coupling reactions − and later utilized in polarographic quantitative analysis. − On the basis of the presence of four nitrogens in a row in its molecule, the compound obtained the acronym “tetrazene”; based on the chemical name of structure II, it obtained the abbreviation GNGT.…”