Tandem deprotonation/azide–tetrazole tautomerization of 4,6-diazido-N-nitro-1,3,5-triazin-2-amine in dimethylsulfoxide solutions: a theoretical study

文献信息

发布日期 2015-05-26
DOI 10.1039/C5CP02096D
影响因子 3.676
作者

S. V. Chapyshev


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摘要

4,6-Diazido-N-nitro-1,3,5-triazin-2-amine (2) is a new promising high-energy organic compound that isomerizes in dimethylsulfoxide (DMSO) solutions to form unknown products with interesting 13C and 15N NMR spectroscopic characteristics. To identify these products, the relative energies and the 13C and 15N chemical shifts were calculated for various prototropic and valence isomers of 2. It was found that this diazide in DMSO solutions exists in equilibrium with the deprotonated form of 5-azido-N-nitrotetrazolo[1,5-a][1,3,5]triazin-7-amine (8). The anion 8 is also observed in DMSO solutions of energetic salts derived from 2 and guanidines or 4H-1,2,4-triazol-4-amines. The tandem transformations of 2 in DMSO solutions found may be of interest from both theoretical and practical points of view, for instance, in the synthesis of new energetic materials, using the reactions of anion 8 with various electrophilic agents.

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来源期刊

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
自引率: 10.3%
年发文量: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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