Synthesis and properties of acetamidinium salts

Abstract

BackgroundAcetamidines are starting materials for synthesizing many chemical substances, such as imidazoles, pyrimidines and triazines, which are further used for biochemically active compounds as well as energetic materials. The aim of this study was to synthesise and characterise a range of acetamidinium salts in order to overcome the inconvenience connected with acetamidinium chloride, which is the only commercially available acetamidinium salt.ResultsAcetamidinium salts were synthesised and characterised by elemental analysis, mass spectrometry, NMR and - in the case of energetic salts - DTA. The structures of previously unknown acetamidinium salts were established by X-ray diffraction analysis. Hygroscopicities in 90% humidity of eight acetamidinium salts were evaluated.ConclusionsThe different values of hygroscopicity are corroborated by the structures determined by X-ray analysis. The acetamidinium salts with 2D layered structures (acetamidinium nitrate, formate, oxalate and dinitromethanide) show a lack of hygroscopicity, and the compounds with 3D type of structure (acetamidinium chloride, acetate, sulphate and perchlorate) and possessing rather large cavities are quite hygroscopic.

New Assembly of Acetamidinium Nitrate Modulated by High Pressure

“…However, one problem is the critical range for this transition seems somewhat high in practical applications. In this work, we tailor the cation with methyl group replacing hydroxyl and prepare the energetic material acetamidinium nitrate (C 2 N 2 H 7 + ·NO 3 – , AN) . Under ambient conditions, AN crystallizes in space group P 2 1 / m with Z = 2 in the unit cell.…”

“…In this work, we tailor the cation with methyl group replacing hydroxyl and prepare the energetic material acetamidinium nitrate (C 2 N 2 H 7 + •NO 3 − , AN). 39 Under ambient conditions, AN crystallizes in space group P2 1 /m with Z = 2 in the unit cell. The lattice parameters are a = 6.457(2) Å, b = 6.442(2), c = 6.884(1), and β = 97.56(2)°.…”

Geometric Isomerism of an Acetamidino Derivative Determined by NMR Investigations

“…The 1 H NMR spectrum of 5 a in MeOD caught our attention for the presence of doubled signal, in an approximately 1:1 ratio, relative to the acetamidino methyl (s at 2.23 and s at 2.31 ppm) and methylene connecting the two nitrogens (both t, 3.39 and 3.54 ppm) (Figure A ). After being in vacuo dried, compound 5 a was lyophilizated to completely remove the residual water; indeed, the prominent feature of acetaminium bromides is the relatively high hygroscopicity . After this step of lyophilization, the 1 H NMR spectrum was newly registered and a remarkable change of chemical shifts was still observed: the signals at 2.23 and 3.39 ppm were unchanged, while the other two signals (2.31 and 3.54 ppm) disappeared (Figure B ).…”

X-ray powder diffraction data for acetamidinium formate C3H8N2O2, elimination of preferred orientation effect

“…After cooling, the white material obtained (title compound, Figure 1) was washed with methanol and dried. Melting point, elemental analysis, and NMR spectra were identical with those described in literature (Jalový et al, 2011).…”

“…A mixture of trimethyl orthoacetate and ammonium formate at molar ratio 1:2, respectively, was heated under reflux for 2.5 h (Jalový et al , 2011). After cooling, the white material obtained (title compound, Figure 1) was washed with methanol and dried.…”