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Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations

4,8-Dihydrodifurazano[3,4-b,e]pyrazine (DFP) is one kind of parent compound for the synthesis of various promising difurazanopyrazine derivatives. In this paper, eleven series of energetic salts composed of 4,8-dihydrodifurazano[3,4-b,e]pyrazine-based anions and ammonium-based cations were designed....

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Autores principales: Duan, Binghui, Liu, Ning, Wang, Bozhou, Lu, Xianming, Mo, Hongchang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6774342/
https://www.ncbi.nlm.nih.gov/pubmed/31487829
http://dx.doi.org/10.3390/molecules24183213
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author Duan, Binghui
Liu, Ning
Wang, Bozhou
Lu, Xianming
Mo, Hongchang
author_facet Duan, Binghui
Liu, Ning
Wang, Bozhou
Lu, Xianming
Mo, Hongchang
author_sort Duan, Binghui
collection PubMed
description 4,8-Dihydrodifurazano[3,4-b,e]pyrazine (DFP) is one kind of parent compound for the synthesis of various promising difurazanopyrazine derivatives. In this paper, eleven series of energetic salts composed of 4,8-dihydrodifurazano[3,4-b,e]pyrazine-based anions and ammonium-based cations were designed. Their densities, heats of formation, energetic properties, impact sensitivity, and thermodynamics of formation were studied and compared based on density functional theory and volume-based thermodynamics method. Results show that ammonium and hydroxylammonium salts exhibit higher densities and more excellent detonation performance than guanidinium and triaminoguanidinium salts. Therein, the substitution with electron-withdrawing groups (–NO(2), –CH(2)NF(2), –CH(2)ONO(2), –C(NO(2))(3), –CH(2)N(3)) contributes to enhancing the densities, heats of formation, and detonation properties of the title salts, and the substitution of –C(NO(2))(3) features the best performance. Incorporating N–O oxidation bond to difurazano[3,4-b,e]pyrazine anion gives a rise to the detonation performance of the title salts, while increasing their impact sensitivity meanwhile. Importantly, triaminoguanidinium 4,8-dihydrodifurazano[3,4-b,e]pyrazine (J4) has been successfully synthesized. The experimentally determined density and H(50) value of J4 are 1.602 g/cm(3) and higher than 112 cm, which are consistent with theoretical values, supporting the reliability of calculation methods. J4 proves to be a thermally stable and energetic explosive with decomposition peak temperature of 216.7 °C, detonation velocity 7732 m/s, and detonation pressure 25.42 GPa, respectively. These results confirm that the derivative work in furazanopyrazine compounds is an effective strategy to design and screen out potential candidates for high-performance energetic salts.
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spelling pubmed-67743422019-10-03 Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations Duan, Binghui Liu, Ning Wang, Bozhou Lu, Xianming Mo, Hongchang Molecules Article 4,8-Dihydrodifurazano[3,4-b,e]pyrazine (DFP) is one kind of parent compound for the synthesis of various promising difurazanopyrazine derivatives. In this paper, eleven series of energetic salts composed of 4,8-dihydrodifurazano[3,4-b,e]pyrazine-based anions and ammonium-based cations were designed. Their densities, heats of formation, energetic properties, impact sensitivity, and thermodynamics of formation were studied and compared based on density functional theory and volume-based thermodynamics method. Results show that ammonium and hydroxylammonium salts exhibit higher densities and more excellent detonation performance than guanidinium and triaminoguanidinium salts. Therein, the substitution with electron-withdrawing groups (–NO(2), –CH(2)NF(2), –CH(2)ONO(2), –C(NO(2))(3), –CH(2)N(3)) contributes to enhancing the densities, heats of formation, and detonation properties of the title salts, and the substitution of –C(NO(2))(3) features the best performance. Incorporating N–O oxidation bond to difurazano[3,4-b,e]pyrazine anion gives a rise to the detonation performance of the title salts, while increasing their impact sensitivity meanwhile. Importantly, triaminoguanidinium 4,8-dihydrodifurazano[3,4-b,e]pyrazine (J4) has been successfully synthesized. The experimentally determined density and H(50) value of J4 are 1.602 g/cm(3) and higher than 112 cm, which are consistent with theoretical values, supporting the reliability of calculation methods. J4 proves to be a thermally stable and energetic explosive with decomposition peak temperature of 216.7 °C, detonation velocity 7732 m/s, and detonation pressure 25.42 GPa, respectively. These results confirm that the derivative work in furazanopyrazine compounds is an effective strategy to design and screen out potential candidates for high-performance energetic salts. MDPI 2019-09-04 /pmc/articles/PMC6774342/ /pubmed/31487829 http://dx.doi.org/10.3390/molecules24183213 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Duan, Binghui
Liu, Ning
Wang, Bozhou
Lu, Xianming
Mo, Hongchang
Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations
title Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations
title_full Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations
title_fullStr Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations
title_full_unstemmed Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations
title_short Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine-based Anions and Ammonium-based Cations
title_sort comparative theoretical studies on a series of novel energetic salts composed of 4,8-dihydrodifurazano[3,4-b,e]pyrazine-based anions and ammonium-based cations
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6774342/
https://www.ncbi.nlm.nih.gov/pubmed/31487829
http://dx.doi.org/10.3390/molecules24183213
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