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Synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings

BACKGROUND: Poly nitro aromatic compounds are high energy density materials. Carbon–bonded anionic sigma complexes derived from them have remarkable thermal stability. At present there is a strong requirement for thermally stable insensitive high energy density materials (IHEDMs) in the energetic fi...

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Autores principales: Kulandaiya, Rajamani, Doraisamyraja, Kalaivani
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4338363/
https://www.ncbi.nlm.nih.gov/pubmed/25717344
http://dx.doi.org/10.1186/s13065-014-0078-8
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author Kulandaiya, Rajamani
Doraisamyraja, Kalaivani
author_facet Kulandaiya, Rajamani
Doraisamyraja, Kalaivani
author_sort Kulandaiya, Rajamani
collection PubMed
description BACKGROUND: Poly nitro aromatic compounds are high energy density materials. Carbon–bonded anionic sigma complexes derived from them have remarkable thermal stability. At present there is a strong requirement for thermally stable insensitive high energy density materials (IHEDMs) in the energetic field which necessitates the present investigation. RESULTS: Three new carbon–bonded anionic sigma complexes were synthesized from 2-chloro-1,3,5-trinitrobenzene, 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (1,3-dimethylbarbituric acid) and bases such as triethanolamine, pyridine and N,N-diethylaniline, characterized by UV–VIS, IR, (1)H NMR, (13)C NMR and elemental analysis data. Their molecular structures were further ascertained through single crystal X-ray diffraction studies. TGA/DTA testings were undertaken at four different heating rates (5, 10, 20 and 40 K/min) and energy of activation was determined employing Ozawa and Kissinger plots. CONCLUSIONS: The reported carbon–bonded anionic sigma complexes were prepared through single pot synthesis in good yield with high purity. These complexes are molecular salts comprise of cation and anion moieties. Because of the salt–like nature, they are highly stable upto 300°C and decompose in two stages on further heating. They are stable towards impact of 2 kg mass hammer upto height limit (160 cm) of the instrument. The delocalization of the negative charge and various hydrogen bonds noticed in their crystals are the added factors of their thermal stability. The new insensitive high energy density materials of the present findings may receive attention in the field of energetics in future. [Figure: see text]
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spelling pubmed-43383632015-02-26 Synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings Kulandaiya, Rajamani Doraisamyraja, Kalaivani Chem Cent J Research Article BACKGROUND: Poly nitro aromatic compounds are high energy density materials. Carbon–bonded anionic sigma complexes derived from them have remarkable thermal stability. At present there is a strong requirement for thermally stable insensitive high energy density materials (IHEDMs) in the energetic field which necessitates the present investigation. RESULTS: Three new carbon–bonded anionic sigma complexes were synthesized from 2-chloro-1,3,5-trinitrobenzene, 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (1,3-dimethylbarbituric acid) and bases such as triethanolamine, pyridine and N,N-diethylaniline, characterized by UV–VIS, IR, (1)H NMR, (13)C NMR and elemental analysis data. Their molecular structures were further ascertained through single crystal X-ray diffraction studies. TGA/DTA testings were undertaken at four different heating rates (5, 10, 20 and 40 K/min) and energy of activation was determined employing Ozawa and Kissinger plots. CONCLUSIONS: The reported carbon–bonded anionic sigma complexes were prepared through single pot synthesis in good yield with high purity. These complexes are molecular salts comprise of cation and anion moieties. Because of the salt–like nature, they are highly stable upto 300°C and decompose in two stages on further heating. They are stable towards impact of 2 kg mass hammer upto height limit (160 cm) of the instrument. The delocalization of the negative charge and various hydrogen bonds noticed in their crystals are the added factors of their thermal stability. The new insensitive high energy density materials of the present findings may receive attention in the field of energetics in future. [Figure: see text] Springer International Publishing 2015-02-01 /pmc/articles/PMC4338363/ /pubmed/25717344 http://dx.doi.org/10.1186/s13065-014-0078-8 Text en © Kulandaiya and Doraisamyraja; licensee Springer. 2015 This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly credited. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research Article
Kulandaiya, Rajamani
Doraisamyraja, Kalaivani
Synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings
title Synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings
title_full Synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings
title_fullStr Synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings
title_full_unstemmed Synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings
title_short Synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings
title_sort synthesis of a new class of carbon–bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials –– implications from impact sensitivity and thermal testings
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4338363/
https://www.ncbi.nlm.nih.gov/pubmed/25717344
http://dx.doi.org/10.1186/s13065-014-0078-8
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