Related Experiment Video
Updated: Aug 19, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Form III of 2,2',4,4',6,6'-hexanitroazobenzene (HNAB-III)
Mark A Rodriguez1, Charles F Campana, A David Rae
1PO Box 5800, MS 1411, Sandia National Laboratories, Albuquerque, New Mexico 87185-1411, USA. marodri@sandia.gov
Abstract:
The crystal structure of form III of the title compound, HNAB [systematic name: bis(2,4,6-trinitrophenyl)diazene], C12H4N8O12, has finally been solved as a pseudo-merohedral twin (monoclinic space group P2(1), rather than the orthorhombic space group C222(1) suggested by diffraction symmetry) using a dual space recycling method. The significant differences in the room-temperature densities of the three crystalline forms allow examination of molecular differences due to packing arrangements. An interesting relationship with the stilbene analog, HNS, is discussed. Interatomic separations are compared with other explosives and/or nitro-containing compounds.
More Related Videos
Related Concept Videos
Criteria for Aromaticity and the Hückel 4n + 2 Rule
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n + 2 rule.
Nomenclature of Aryl and Heterocyclic Amines
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Electrophilic Aromatic Substitution: Nitration of Benzene
Diazonium Group Substitution: –OH and –H
Nucleophilic Aromatic Substitution: Elimination–Addition

