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N ‐Acetonitrile Functionalized Nitropyrazoles: Precursors to Insensitive Asymmetric N ‐Methylene‐C Linked Azoles
Author(s) -
Kumar Dheeraj,
Imler Gregory H.,
Parrish Damon A.,
Shreeve Jean'ne M.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700786
Subject(s) - acetonitrile , methylene , chemistry , azole , medicinal chemistry , stereochemistry , organic chemistry , microbiology and biotechnology , biology , antifungal
Properties of energetic compounds obtained by linking energetic pyrazoles to tetrazoles by means of N ‐methylene‐ C bridges can be fine‐tuned. Reactions of pyrazole derivatives with chloroacetonitrile followed by conversion of the cyano group to tetrazole using click reactions in the presence of zinc chloride result in asymmetric N ‐methylene‐ C bridged azole‐based energetic compounds. All the compounds were thoroughly characterized by IR and NMR [ 1 H, 13 C { 1 H}, 15 N ] spectroscopy, elemental analysis, and differential scanning calorimetry (DSC), and for two compounds, further supported by single‐crystal X‐ray diffraction studies. Heats of formation and detonation performances were calculated using Gaussian 03 and EXPLO5 v6.01 programs, respectively. Initial studies show that this new approach is promising for synthesizing less sensitive energetic compounds with fine‐tuned properties.