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Comparative simulation study of chemical synthesis of functional DADNE material

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Abstract

Amorphous molecular simulation to model the reaction species in the synthesis of chemically inert and energetic 1,1-diamino-2,2-dinitroethene (DADNE) explosive material was performed in this work. Nitromethane was selected as the starting reactant to undergo halogenation, nitration, deprotonation, intermolecular condensation, and dehydration to produce the target DADNE product. The Materials Studio (MS) forcite program allowed fast energy calculations and reliable geometric optimization of all aqueous molecular reaction systems (0.1–0.5 M) at 283 K and 298 K. The MS forcite-computed and Gaussian polarizable continuum model (PCM)-computed results were analyzed and compared in order to explore feasible reaction pathways under suitable conditions for the synthesis of DADNE. Through theoretical simulation, the findings revealed that synthesis was possible, and a total energy barrier of 449.6 kJ mol−1 needed to be overcome in order to carry out the reaction according to MS calculation of the energy barriers at each stage at 283 K, as shown by the reaction profiles. Local analysis of intermolecular interaction, together with calculation of the stabilization energy of each reaction system, provided information that can be used as a reference regarding molecular integrated stability.

Materials Studio software has been suggested for the computation and simulation of DADNE synthesis

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Acknowledgement

The authors would like to thank the National Center for High-Performance Computing for support with calculation facilities.

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Authors and Affiliations

  1. Department of Chemical and Materials Engineering, Chung Cheng Institute of Technology, National Defense University, Taoyuan, 33509 Taiwan, Republic of China

    Min Hsien Liu & Chuan Wen Liu

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  1. Min Hsien Liu
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  2. Chuan Wen Liu
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Correspondence to Min Hsien Liu.

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Liu, M.H., Liu, C.W. Comparative simulation study of chemical synthesis of functional DADNE material. J Mol Model 23, 4 (2017). https://doi.org/10.1007/s00894-016-3182-y

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  • DOI: https://doi.org/10.1007/s00894-016-3182-y

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