title: Synthesis of a new class of carbon-bonded anionic sigma complexes with 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate moiety as insensitive high energy density materials -- implications from impact sensitivity and thermal testings.
abstract: BACKGROUND
  Poly nitro aromatic compounds are high energy density materials. Carbon-bonded anionic sigma complexes derived from them have remarkable thermal stability. At present there is a strong requirement for thermally stable insensitive high energy density materials (IHEDMs) in the energetic field which necessitates the present investigation.
  
  
  RESULTS
  Three new carbon-bonded anionic sigma complexes were synthesized from 2-chloro-1,3,5-trinitrobenzene, 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (1,3-dimethylbarbituric acid) and bases such as triethanolamine, pyridine and N,N-diethylaniline, characterized by UV-VIS, IR, (1)H NMR, (13)C NMR and elemental analysis data. Their molecular structures were further ascertained through single crystal X-ray diffraction studies. TGA/DTA testings were undertaken at four different heating rates (5, 10, 20 and 40 K/min) and energy of activation was determined employing Ozawa and Kissinger plots.
  
  
  CONCLUSIONS
  The reported carbon-bonded anionic sigma complexes were prepared through single pot synthesis in good yield with high purity. These complexes are molecular salts comprise of cation and anion moieties. Because of the salt-like nature, they are highly stable upto 300°C and decompose in two stages on further heating. They are stable towards impact of 2 kg mass hammer upto height limit (160 cm) of the instrument. The delocalization of the negative charge and various hydrogen bonds noticed in their crystals are the added factors of their thermal stability. The new insensitive high energy density materials of the present findings may receive attention in the field of energetics in future. Graphical AbstractA new class of carbon-bonded anionic sigma complexes as insensitive high energy density materials.
authors.affiliation: Post Graduate & Research Department of Chemistry, Seethalakshmi Ramaswami College, Affiliated to Bharathidasan University, Tiruchirappalli, 620 002 Tamil Nadu India.
authors.forename: Rajamani
authors.initials: R
authors.lastname: Kulandaiya
authors.affiliation: Post Graduate & Research Department of Chemistry, Seethalakshmi Ramaswami College, Affiliated to Bharathidasan University, Tiruchirappalli, 620 002 Tamil Nadu India.
authors.forename: Kalaivani
authors.initials: K
authors.lastname: Doraisamyraja
keywords: 1,3-dimethyl barbituric acid; 2-chloro-1,3,5-trinitrobenzene; Carbon–bonded anionic sigma complexes; Insensitive high energy density materials; Molecular salts; Thermal studies