Open AccessImpact of Stereo- and Regiochemistry on Energetic Materials
Author(s) -
Lisa M. Barton,
Jacob T. Edwards,
E. Johnson,
Eric J. Bukowski,
Rosario C. Sausa,
Edward F. C. Byrd,
Joshua A. Orlicki,
Jesse J. Sabatini,
Phil S. Baran
Publication year - 2019
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b06961
Subject(s) - regioselectivity , chemistry , propellant , eutectic system , explosive material , cyclobutane , chemical engineering , computational chemistry , organic chemistry , alloy , catalysis , engineering , ring (chemistry)
The synthesis, physical properties, and calculated performances of six stereo- and regioisomeric cyclobutane nitric ester materials are described. While the calculated performances of these isomers, as expected, were similar, their physical properties were found to be extremely different. By alteration of the stereo- and regiochemistry, complete tunability in the form of low- or high-melting solids, stand-alone melt-castable explosives, melt-castable explosive eutectic compounds, and liquid propellant materials was obtained. This demonstrates that theoretical calculations should not be the main factor in driving the design of new materials and that stereo- and regiochemistry matter in the design of compounds of potential relevance to energetic formulators.