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Impact of Stereo- and Regiochemistry on Energetic Materials

preprint
submitted on 03.07.2019 and posted on 04.07.2019 by Lisa M. Barton, Jacob T. Edwards, Eric C. Johnson, Eric J. Bukowski, Rosario C. Sausa, Edward F. C. Byrd, Joshua A. Orlicki, Jesse J. Sabatini, Phil Baran
The synthesis, physical properties and calculated performances of six stereo- and regioisomeric cyclobutane nitric ester materials is described. While the calculated performances of these isomers, as expected, were similar, their physical properties were found to be extremely different. By altering the stereo- and regiochemistry, complete tunability in the form of low-or high-melting solids, standalone melt-castable explosives, melt-castable explosive eutectic compounds, and liquid propellant materials were obtained. This study demonstrates that theoretical calculations should not be the main factor in driving the design and synthesis of new materials, and that stereo- and regiochemistry offer a new dimension to consider when designing compounds of potential relevance to energetic formulators.

Funding

DARPA, Agreement No. HR0011-18-9-0021

History

Email Address of Submitting Author

pbaran@scripps.edu

Institution

Scripps Research

Country

United States of America

ORCID For Submitting Author

0000-0001-9193-9053

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Energetics Version 1

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in Journal of the American Chemical Society

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