Computational Study on the Comparative Synthesis of Energetic FOX-7 Derivatives

摘要

Ethene and two kinds of nitrating reagents (HNO3 and N2O5) were included in respective molecular systems, which progressed through a two-stage electrophihc and free radical nitrosubstitution, resulting in the corresponding nitroethene compounds. Subsequent halogenation (using Cl-2 and Br-2) and amination (using ammonia) were then performed, also by electrophilic and radical substitution, to produce the target 1,1-diamino-2,2-dinitroethene (FOX-7) derivatives. All transition state species were identified using a two- or three-structure Synchronous Transit-Guided Quasi-Newton between the Cartesian coordinates of the related molecular systems at specific reaction stages. The modeling results suggest that N2O5, is the better agent for nitration and bromine is suitable for use in halogenation. The comparable activation energies throughout the reaction stages were considered to imply the most feasible pathways of FOX-7 synthesis.