Nitroguanidines.

McKay, A. F.

doi:10.1021/cr60159a003

Cited by 64 publications

(43 citation statements)

References 73 publications

(167 reference statements)

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“…However, the elimination of nitramine (which decomposes to N 2 O and H 2 O) leads to aminoguanidine B. The formation of diaminoguanidine as the second by-product can be explained by a further reaction of 2 with an additional equivalent of hydrazine to form species C, which under the elimination of nitramine forms diaminoguanidine D (Scheme 2) [10]. These findings are also corroborated by an experiment using a larger excess of hydrazine hydrate (2.2 eq.)…”

Section: Synthesismentioning

confidence: 99%

1-Amino-3-nitroguanidine (ANQ) in High-performance Ionic Energetic Materials

Fischer

Klapötke

Stierstorfer

2012

Zeitschrift Für Naturforschung B

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1-Amino-3-nitroguanidine (ANQ, 2) was synthesized via hydrazinolysis of nitroguanidine (1). An appropriate Lewis structure of ANQ is drawn based on VB calculations. Due to its basicity, it can be protonated by strong mineral acids or acidic heterocycles. In order to synthesize new energetic materials the nitrate (3) and perchlorate (4) salts of 1-amino-3-nitroguanidine were synthesized by protonation of 2 with 40 % nitric acid and 60 % perchloric acid, respectively. 5-Nitrimino-1,4H-tetrazole obtained by reacting 5-amino-1H-tetrazole with 100 % HNO 3 was used to synthesize the nitriminotetrazolate salt 5. Furthermore, the dinitramide salt 6 of 1-amino-3-nitroguanidine was synthesized by metathesis reaction of silver dinitramide and 1-amino-3-nitroguanidinium chloride. The dinitroguanidinate salt 7 was synthesized by protonation of 2 with 1,3-dinitroguanidine, which was prepared from nitroguanidine in anhydrous nitric acid/N 2 O 5 . All compounds were fully characterized by singlecrystal X-ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, and DSC measurements. The heats of formation of 2 -7 were calculated using the atomization method based on CBS-4M enthalpies. With these values and the experimental (X-ray) densities several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code. In addition, the sensitivities towards impact, friction and electrical discharge were tested using the BAM drophammer, friction tester as well as a small-scale electrical discharge device. A Koenen test with 1-amino-3-nitroguanidinium nitrate (3) was carried out in order to evaluate its explosive performance and shipping classification.

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Section: Synthesismentioning

confidence: 99%

1-Amino-3-nitroguanidine (ANQ) in High-performance Ionic Energetic Materials

Fischer

Klapötke

Stierstorfer

2012

Zeitschrift Für Naturforschung B

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“…Formation of the thiazoline derivative is reminiscent of the preparation of cyclic nitroguanidine derivatives from diamines and nitroguanidine with liberation of ammonia (21,22). The possibility that 2-nitramino-4-carboxylthiazoline might arise from reaction of cysteine with N-methyl-N1-nitroguanidine can be eliminated, since no reaction took place on mixing cysteine and N-methyl-N1-nitroguanidine for 20 h at room temperature in aqueous ethanol.…”

Section: Reactions Of Cysteine With Ngmentioning

confidence: 99%

Reactions of cysteine with N-methyl-N-nitroso-p-toluenesulfonamide and N-methyl-N′-nitro-N-nitrosoguanidine

Schulz¹,

McCalla²

1969

Can. J. Chem.

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The reaction between cysteine and N-methyl-N-nitroso-p-toluenesulfonamide affords almost quantitative yields of cystine and N-methyl-p-toluenesuIfonaniide. A mechanism based on the intermediacy of the S-nitroso derivative of cysteine and the intermediate formation of nitric oxide is proposed. Nitrous oxide is shown to be a final product. In the reaction of cysteine with N-methyl-N'-nitro-N-nitrosoguanidine a substantial yield of 2-nitramino-4-carboxyl-thiazoline is obtained. Cystine, N-methyl-N'-nitroguanidine and S-methylcysteine are formed in lesser amounts. The major product arises from nucleophilic attack on the iniino carbon of N-methyl-N'-nitro-N-nitrosoguanidine. Concomitant elimination of the methylnitrosamino group accounts for the methylating ability of the system. Canadian Journal of Chemistry, 47, 2021 (1969) Previous work in this laboratory has shown that deoxyribonucleic acid (DNA) becomes methylated when it is allowed to react in vitro with either N-methyl-N'-nitro-N-nitrosoguanidine (NG) or with N-methyl-N-nitroso-p-toluenesulfonamide (MNTS) (1). Addition of cysteine to the reaction mixture was found to increase methylation by N G but to decrease dramatically methylation by MNTS, results which are of considerable interest in view of biological studies showing that cysteine has a protective action against certain types of alkylating agents (2).Both N G and MNTS are well-established sources of diazomethane in their reactions with aqueous base (3,4). For the reactions of N G and MNTS with nucleophilic reagents other than oxygen nucleophiles, a variety of products are reported. McKay and Wright (5) demonstrated that primary alkyl or aryl amines react with N G with the elimination of the methylnitrosamino group and the formation of N-substituted nitroguanidines. The only secondary amine to react with N G to give a Ndisubstituted-Nf-nitroguanidine is dimethylamine. Reaction of N G with other secondary amines resulted in denitrosation (6). In the reaction of N G with azide ion the methylnitrosamino group is eliminated and 5-nitroaminotetrazole is formed by cyclization of the intermediate nitrogiianylazide (7). The reaction between MNTS and piperidine results in transfer of the nitroso group to form N-nitrosopiperidine without the formation of any diazomethane (4). Low yields of diphenylnitrosamine are reported to result from reaction of MNTS with diphenylamine (8).Thus, while the existing literature pointed to the fact that the N-methyl-N-nitroso compounds under consideration exhibit two centers susceptible to nucleophilic attack, resulting in loss of the methylnitrosamino group and the nitroso function respectively, no information was available on their reactions with mercaptans. We report here data that provide a reasonable explanation for the difference in the behavior of N G and MNTS in the presence of cysteine. Results and Discussion Reactions of Cysteitze rvith M N T SThe reactions of cysteine with MNTS were carried out at room temperature in aqueous 25 % ethanol at pH 7 in an atmosphere of nit...

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“…1-Amino-3-nitroguanidine (1, ANQ) can be described as the aminated sister compound of the famous 1-nitroguanidine (NQ) [1]. The next step in the preparation of mixed aminonitroguanidines would be the synthesis of 1,3-diamino-5-nitroguanidine (DANQ), which is completely unknown yet ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Inorganic Amino-Nitro-Guanidinium Derivatives

Fischer¹,

Klapötke²,

Lux³

et al. 2012

Crystals

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1-Amino-3-nitroguanidine (ANQ, 1) was synthesized by hydrazinolysis of nitroguanidine (NQ) with hydrazine hydrate. Four different amino-nitroguanidinium salts (chloride (2), bromide (3), iodide (4) and sulfate (5)) were synthesized and structurally characterized by low-temperature X-ray diffraction. The halides 2-4 could only be obtained crystalline as monohydrates. In addition, they were characterized by NMR and vibrational spectroscopy, elemental analysis and the sensitivities towards impact, friction and electrostatic discharge were determined. The compounds can be used in silver (AgX, X = Cl, Br, I) and barium (BaSO 4 ) based metathesis reactions in order to form more complex salts of 1-amino-nitroguanidine.

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Nitroguanidines.

Cited by 64 publications

References 73 publications

1-Amino-3-nitroguanidine (ANQ) in High-performance Ionic Energetic Materials

1-Amino-3-nitroguanidine (ANQ) in High-performance Ionic Energetic Materials

Reactions of cysteine with N-methyl-N-nitroso-p-toluenesulfonamide and N-methyl-N′-nitro-N-nitrosoguanidine

Inorganic Amino-Nitro-Guanidinium Derivatives

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