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Energetic N ‐Nitramino/ N ‐Oxyl‐Functionalized Pyrazoles with Versatile π–π Stacking: Structure–Property Relationships of High‐Performance Energetic Materials
Author(s) -
Yin Ping,
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.201608499
Subject(s) - stacking , explosive material , energetic material , crystal structure , diffraction , materials science , crystallography , face (sociological concept) , property (philosophy) , pyrazole , chemistry , combinatorial chemistry , computer science , stereochemistry , physics , organic chemistry , optics , social science , philosophy , epistemology , sociology
N‐Nitramino/N‐oxyl functionalization strategies were employed to investigate structure–property relationships of energetic materials. Based on single‐crystal diffraction data, π–π stacking of pyrazole backbones can be tailored effectively by energetic functionalities, thereby resulting in diversified energetic compounds. Among them, hydroxylammonium 4‐amino‐3,5‐dinitro‐1H‐pyrazol‐1‐olate and dipotassium N,N′‐(3,5‐dinitro‐1H‐pyrazol‐1,4‐diyl)dinitramidate, with unique face‐to‐face π–π stacking, can be potentially used as a high‐performance explosive and an energetic oxidizer, respectively.