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Enhancing Energetic Properties and Sensitivity by Incorporating Amino and Nitramino Groups into a 1,2,4‐Oxadiazole Building Block
Author(s) -
Tang Yongxing,
Gao Haixiang,
Mitchell Lauren A.,
Parrish Damon A.,
Shreeve Jean'ne M.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509985
Subject(s) - oxadiazole , detonation , hydrogen bond , block (permutation group theory) , ring (chemistry) , chemistry , molecule , crystal structure , sensitivity (control systems) , combinatorial chemistry , computational chemistry , crystallography , explosive material , organic chemistry , mathematics , engineering , electronic engineering , geometry
A single nitrogen‐rich heterocyclic ring with many energetic groups is expected to exhibit excellent detonation performance. We report an effective approach for the synthesis of 3‐amino‐5‐nitramino‐1,2,4‐oxadiazole, which has nitramino and amino groups in the same building block. The single‐crystal X‐ray structure shows layered hydrogen‐bonding pairs as well as the presence of a water molecule which ensure insensitivity. Through incorporation of a cation, the hydrazinium or hydroxylammonium salts exhibit good energetic performance and acceptable sensitivities.