The molecular configuration of 1,4-dimethyl-5-imino-tetrazole

Bryden, J. H.

doi:10.1107/s0365110x5700050x

Cited by 4 publications

(3 citation statements)

References 2 publications

(2 reference statements)

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“…Both of these isomers may be protonated by strong mineral acids or methylated further. Though a small number of salts (namely hydrohalides) of monomethylated and polymethylated 5-aminotetrazoles are known, the only potentially energetic salts found in the literature are the nitrate and picrate of 4 and the picrate 9b and nitrate 6b of 1,4-dimethyl-5-iminotetrazole ( 5 ). However, the physical and energetic properties of the known nitrates remain largely unknown, and the potential of polymethylated tetrazolium cations remains unclear.…”

Section: Introductionmentioning

confidence: 99%

Salts of Methylated 5-Aminotetrazoles with Energetic Anions

et al. 2007

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1-methyl-5-aminotetrazole (4, MAT) can easily be protonated by strong acids, yielding known but largely uninvestigated 1-methyl-5-aminotetrazolium nitrate (4a) and perchlorate (4b). Methylation, rather than protonation, of 4 with iodomethane followed by the exchange of the iodide (5a) for nitrate (5b), perchlorate (5c), azide (5d), and dinitramide (5e) yields a new family of energetic methylated aminotetrazole salts. In all cases, stable salts were obtained and fully characterized by vibrational (IR, Raman) spectroscopy, multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, and X-ray structure determination. Compounds 4a, 4b, and 5c crystallize in the monoclinic space group P2(1)/n, whereas compounds 5b and 5e crystallize in the orthorhombic space group P2(1)2(1)2(1) and 5d in the orthorhombic Fddd. Initial safety testing (impact, friction, and electrostatic sensitivity) and thermal stability measurements (DSC) were also carried out. The MAT salts all exhibit good thermal stabilities (decomposition above 150 degrees C). The constant volume energies of combustion (DeltacU) of 4a, 5b, 5d, and 5e were determined to be -2510(10) cal/g, -3190(30) cal/g, -4500(100) cal/g, and -2570(70) cal/g, respectively, experimentally using oxygen bomb calorimetry. From the experimentally determined density, chemical composition and energies of formation (back calculated from the heats of combustion), the detonation pressures and velocities of 4a (8100 m/s, 25.6 GPa), 5b (7500 m/s, 20.2 GPa), 5d (8200 m/s, 21.7 GPa), and 5e (7500 m/s, 21.2 GPa) were predicted using the EXPLO5 code.

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Section: Introductionmentioning

confidence: 99%

Salts of Methylated 5-Aminotetrazoles with Energetic Anions

et al. 2007

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“…21434(14) .26792(15) .28923(15) .25729 (13) .20545 (11) .18286 ( 11) .11 852(12) .00506 ( 12) . (9) .00308 (10) .00305 (9) .00257 (9) ,00206 (7) .00201 (7) .00213 (7) ,00245 (8) .00282 ( 10) .00377 (13) .00369 (11) .00452 (12) .00247 (9) . …”

Section: Losung Der Strukturmentioning

confidence: 97%

“….00015 (10) .00049 (11) .00043 (9) .00065 (8) .00032 (10) .00064 (9) .00026 (9) .00026 (11) .00039( 1 1)…”

Section: P13mentioning

confidence: 98%

Winkelung eines aromatischen Systems durch den sterischen Effekt eines rotationsgehemmten Substituenten: Molekül‐ und Kristallstruktur von 3‐Diisopropylamino‐benzisothiazol‐1.1‐dioxid

Hettler¹

1969

Chem. Ber.

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Wie mit dreidimensionalen Rontgendaten gezeigt wird, kristallisiert 3-Diisopropylaminobenzisothiazol-1.1-dioxid in der orthorhombischen Raumgruppe Pbca mit der Elementarzelle a = 14.139 A, b = 11.064 A, c = 17.405 A. Die Bestimmung der Lage des Schwefelatoms aus der Patterson-Funktion war zweideutig, da dieses Atom auf der c-Gleitebene liegt. Beide Losungen fuhrten zu sinnvollen Strukturen, von denen aber nur eine zu R = 0.046 verfeinert werden konnte. Die Substituenten um den Aminostickstoff sind planar angeordnet und bilden einen Winkel von 14"4' n i t der Isothiazolebene. In dem Bestreben, volle Mesomerie zu erreicheu, suchen die Atome des Molekuls sich eben anzuordnen, wobei die zum Aromaten ,,endo-standige" Isopropylgruppe einen Druck auf den Benzolring ausubt, diesen staucht und um 6"4' von der Tsothiazolebene wegdruckt: das aromatische System ist gewinkelt.In 3-Amino-benzisothiazol-1.

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C3h6 - C3h9 (3-6-20 - 3-9-13)

Schudt¹,

Weitz²

Structure Data of Organic Crystals

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The molecular configuration of 1,4-dimethyl-5-imino-tetrazole

Cited by 4 publications

References 2 publications

Salts of Methylated 5-Aminotetrazoles with Energetic Anions

Salts of Methylated 5-Aminotetrazoles with Energetic Anions

Winkelung eines aromatischen Systems durch den sterischen Effekt eines rotationsgehemmten Substituenten: Molekül‐ und Kristallstruktur von 3‐Diisopropylamino‐benzisothiazol‐1.1‐dioxid

C3h6 - C3h9 (3-6-20 - 3-9-13)

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