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Computational study on the comparative synthesis of energetic FOX‐7 derivatives
Author(s) -
Liu MinHsien,
Cheng KenFa,
Chen Cheng,
Hong YawSun
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.22020
Subject(s) - nitration , chemistry , electrophile , halogenation , electrophilic substitution , reagent , bromine , computational chemistry , amination , electrophilic amination , quantum chemical , transition state , medicinal chemistry , combinatorial chemistry , molecule , organic chemistry , catalysis
Ethene and two kinds of nitrating reagents (HNO 3 and N 2 O 5 ) were included in respective molecular systems, which progressed through a two‐stage electrophilic 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 N 2 O 5 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. © 2009 Wiley Periodicals, Inc. Int J Quantum Chem, 2010