Azide–Tetrazole Ring‐Chain Isomerism in Polyazido‐1,3,5‐triazines, Triazido‐s‐heptazine, and Diazidotetrazines

Abstract

The azide-tetrazole isomerism in several polyazido-1,3,5-triazines, triazido-sym-heptazine, and some diazido-1,2,4,5-tetrazines was investigated by ab initio quantum chemical methods in order to determine whether the polyazides are suitable starting materials for the synthesis of the isomeric tetrazoles. The effects of solvation in CCl 4 , DMSO and water on this isomerism were included using the self consistent reaction field (SCRF) method. The effect of amino-and nitrosubstituents on the azide-tetrazole isomerism was also examined. In the gas phase all investigated polyazidoheterocycles do not cyclize to form tetrazoles. An electron-donating amino group favors the ring closure to tetrazoles, whereas an electron-withdrawing nitro group favors the azides. Solvation in polar solvents favors the formation of a tetrazole ring system

Preparation, morphologies and thermal behavior of high nitrogen compound 2-amino-4,6-diazido-s-triazine and its derivatives

“…It may caused by localized accelerated fast decomposition due to self-heating. It has been found that when one azide substituent of cyanuric azide was replaced by the electron-donating amino group, it would have three planar isomers, whose successive cyclization leads to 16 isomers all with C1 symmetry [35]. These isomers may make the decomposition channels of DAAT more complicated.…”

Multistep Thermolysis Mechanisms of Azido-s-triazine Derivatives and Kinetic Compensation Effects for the Rate-Limiting Processes

“…By replacing one azide substituent of cyanuric azide (CA) with the electron-donating amino group, three planar isomers of DAAT can be obtained. Their successive cyclization leads to 16 isomers42 …”

Azide‐Containing High Energy Materials

“…80,81 Controlled decomposition studies and detonation studies of TAT under pressure were performed to give carbon nitrides and graphite particles, respectively. 86 85 The azido -tetrazole ring -chain isomerism in polyazido -triazines, -tetrazines and heptazine has been discussed by extensive calculations.…”