N ‐Acetonitrile Functionalized Nitropyrazoles: Precursors to Insensitive Asymmetric N ‐Methylene‐C Linked Azoles
Publication type: Journal Article
Publication date: 2017-05-19
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
28445629
General Chemistry
Catalysis
Organic Chemistry
Abstract
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.
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56
Total citations:
56
Citations from 2025:
16
(28.57%)
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GOST
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Kumar D. et al. N ‐Acetonitrile Functionalized Nitropyrazoles: Precursors to Insensitive Asymmetric N ‐Methylene‐C Linked Azoles // Chemistry - A European Journal. 2017. Vol. 23. No. 33. pp. 7876-7881.
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Kumar D., Imler G. H., Parrish D. A., Shreeve J. M. N ‐Acetonitrile Functionalized Nitropyrazoles: Precursors to Insensitive Asymmetric N ‐Methylene‐C Linked Azoles // Chemistry - A European Journal. 2017. Vol. 23. No. 33. pp. 7876-7881.
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RIS
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TY - JOUR
DO - 10.1002/chem.201700786
UR - https://doi.org/10.1002/chem.201700786
TI - N ‐Acetonitrile Functionalized Nitropyrazoles: Precursors to Insensitive Asymmetric N ‐Methylene‐C Linked Azoles
T2 - Chemistry - A European Journal
AU - Kumar, Dheeraj
AU - Imler, Gregory H
AU - Parrish, Damon A.
AU - Shreeve, Jean'ne M.
PY - 2017
DA - 2017/05/19
PB - Wiley
SP - 7876-7881
IS - 33
VL - 23
PMID - 28445629
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Kumar,
author = {Dheeraj Kumar and Gregory H Imler and Damon A. Parrish and Jean'ne M. Shreeve},
title = {N ‐Acetonitrile Functionalized Nitropyrazoles: Precursors to Insensitive Asymmetric N ‐Methylene‐C Linked Azoles},
journal = {Chemistry - A European Journal},
year = {2017},
volume = {23},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/chem.201700786},
number = {33},
pages = {7876--7881},
doi = {10.1002/chem.201700786}
}
Cite this
MLA
Copy
Kumar, Dheeraj, et al. “N ‐Acetonitrile Functionalized Nitropyrazoles: Precursors to Insensitive Asymmetric N ‐Methylene‐C Linked Azoles.” Chemistry - A European Journal, vol. 23, no. 33, May. 2017, pp. 7876-7881. https://doi.org/10.1002/chem.201700786.