NDLI: Salts of 1-(chloromethyl)-1,1-dimethylhydrazine and ionic liquids

Content Provider	Royal Society of Chemistry (RSC)
Author	Sabaté, Carles Miró Forquet, Valérian Delalu, Henri Jeanneau, Erwann
Copyright Year	2012
Abstract	The reaction of 1,1-dimethylhydrazine with excess dichloromethane led to the formation of the chloride salt of the 1-(chloromethyl)-1,1-dimethylhydrazinium cation ([(CH3)2N(CH2Cl)NH2]Cl, 1). The reaction of 1 with a suitable silver salt provided the nitrate ([(CH3)2N(CH2Cl)NH2][NO3], 2), perchlorate ([(CH3)2N(CH2Cl)NH2][ClO4], 3), azide ([(CH3)2N(CH2Cl)NH2][N3], 4), dicyanamide ([(CH3)2N(CH2Cl)NH2][N(CN)2], 5) and sulphate ([(CH3)2N(CH2Cl)NH2]2[SO4], 6) salts. Compound 6 reacted with barium 5,5′-azobistetrazolate pentahydrate (Ba[N4C–NN–CN4]·5H2O), barium dipicrate tetrahydrate (Ba[(NO2)3Ph–O]2·4H2O) and barium 5-amino-1H-tetrazolate tetrahydrate (Ba[H2N–CN4]2·4H2O) to form the corresponding metathesis products: [(CH3)2N(CH2Cl)NH2]2[N4C–NN–CN4] (7), [(CH3)2N(CH2Cl)NH2][(NO2)3Ph–O] (8) and [(CH3)2N(CH2Cl)NH2][H2N–CN4] (9). Compounds 1–9 were characterized by elemental analysis, mass spectrometry, NMR (1H and 13C) and vibrational spectroscopy (infrared and Raman). Additionally, we measured the 15N NMR spectrum of the nitrate salt 2 and identified the solid state structure of compounds 3, 6, 7 and 8 by low temperature X-ray crystallography (3: Triclinic P, a = 5.983(1) Å, b = 7.502(1) Å, c = 9.335(1) Å; α = 93.86(1)°, β = 101.21(1)°; γ = 91.13(1)°; V = 409.8(1) Å3, 6: Monoclinic C2/c, a = 11.674(2) Å, b = 17.503(3) Å, c = 6.616(1) Å; β = 90.27(1)°; V = 1351.8(4) Å3, 7: Triclinic P, a = 8.851(1) Å, b = 8.872(1) Å, c = 11.529(1) Å; α = 80.98(1)°, β = 83.47(1)°; γ = 71.37(1)°; V = 845.4(1) Å3 and 8: Monoclinic C2/c, a = 24.168(3) Å, b = 7.375(1) Å, c = 17.062(3) Å; β = 116.19(2)°; V = 1351.8(3) Å3). The solid state structure of barium dipicrate hexahydrate (Ba[(NO2)3Ph–O]2·6H2O) was also elucidated: Triclinic P, a = 6.641(1) Å, b = 11.588(1) Å, c = 15.033(1) Å; α = 84.64(1)°, β = 80.07(1)°; γ = 86.80(1)°; V = 1133.8(1) Å3. Furthermore, we studied the thermal properties of compounds 1–9 by differential scanning calorimetry (DSC). Salts 2–4, 8 and 9 fall within the category of ionic liquids. Lastly, the energetic salts were subjected to standard sensitivity tests and a software code was used to predict the detonation parameters and specific impulses of the compounds and their mixtures with an oxidizer.
Starting Page	3691
Ending Page	3699
Page Count	9
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	2
Issue Number	9
Journal	RSC Advances
DOI	10.1039/c2ra00968d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Perchlorate Infrared spectroscopy Differential scanning calorimetry Barium Monoclinic crystal system Sensitivity and specificity Redox Ion Dicyanamide Salt metathesis reaction X-ray crystallography Chloride Nitrate DSC Dichloromethane Raman Triclinic crystal system Azide Mass spectrometry
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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