A Convenient Preparation of Acetamidine.

Crossland, Ingolf; Grevil, Frank S.; Schaumburg, Kjeld; Samuelsson, Bertil; Örn, Ulrika

doi:10.3891/acta.chem.scand.35b-0605

Cited by 16 publications

(14 citation statements)

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“…EPISuite (22 torr) are relatively high so that, barring decomposition, we would expect a strong signal at our working temperatures. Indeed, acetamidine has been reported to decompose at 95°C to yield 70% of acetonitrile 70 , which is consistent with both the fact that acetamidine is not present (or in trace quantities) in our measurements, and that acetonitrile is detected in the measurements performed at 12.5 eV (see Figure 5b). For the ion at m/z 59 (PES shown in Figure 12), which dominates our VUV-MS (low mass side) at all temperatures (see Figure 1), a good fit of the PES could be achieved with the available isomers, and acetamide (C 2 H 5 NO) is found as the most abundant contribution.…”

Section: Molecular Identification Of the Lighter Ions With M/z < 69supporting

confidence: 92%

Molecular Isomer Identification of Titan’s Tholins Organic Aerosols by Photoelectron/Photoion Coincidence Spectroscopy Coupled to VUV Synchrotron Radiation

et al. 2016

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ABSTRACT:The chemical composition of Titan organic haze is poorly known. To address this issue, laboratory analogs named tholins are synthesized, and analyzed by methods requiring often an extraction process in a carrier solvent. These methods exclude the analysis of the insoluble tholins fraction and assume a hypothetical chemical equivalence between soluble and insoluble fractions. In this work, we present a powerful complementary analysis method recently developed on the DESIRS VUV synchrotron beamline at SOLEIL. It involves a soft pyrolysis of tholins at ~230°C and an electron/ion coincidence analysis of the emitted volatiles compounds photoionized by the tunable synchrotron radiation. By comparison with reference photoelectron spectra (PES), the spectral information collected on the detected molecules yields their isomeric structure. The method is more readily applied to light species (m/z ≤ 69), while for heavier ones the number of possibilities and the lack of PES reference spectra in the literature limit its analysis. A notable pattern in the analyzed tholins is the presence of species containing adjacent doubly-bonded N atoms, which might be a signature of heterogeneous incorporation of N 2 in tholins.3

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Section: Molecular Identification Of the Lighter Ions With M/z < 69supporting

confidence: 92%

Molecular Isomer Identification of Titan’s Tholins Organic Aerosols by Photoelectron/Photoion Coincidence Spectroscopy Coupled to VUV Synchrotron Radiation

et al. 2016

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“…Free acetamidine 1e was prepared as previously described. 11 General procedure for the synthesis of 6aa-6ca and 8aa-8ca: After skipped diyne 4a (376 mg; 1.0 mmol) was dissolved in 1,2-dichloroethane (10 mL), benzamidine (1a) (1.20 mmol) was added and the reaction was heated to reflux for 1 hour. After the mixture was cooled, the solvent was removed under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Fully Substituted Pyrimidines

2013

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ABSTRACT:A novel approach to the synthesis of fully substituted pyrimidine derivatives armed with an oxy-functionalized acetate chain at the ring is described. The manifold uses amidines as the nitrogen source and activated skipped diynes as the electrophilic reactive partners in a coupled domino strategy.In the first domino reaction, two consecutive aza-Michael additions assemble the 6-membered ring heterocycle while in the second domino process, a [H]-shift and a [3,3]-sigmatropic-rearrangement lead to the aromatization of the product.Pyrimidine is the most common of the three possible diazines (6-membered aromatic rings with two nitrogen atoms) and constitutes an important pharmacophore endowed with a wide range of pharmacological activities. 1 As such, pyrimidine derivatives have received a great deal of attention from the synthetic community. 2 The most common synthetic approach involves the addition of an N-C-N fragment to a compound possessing a reactive C-C-C connectivity. The most representative example of this type of reactions is the well-known Pinner pyrimidine synthesis which involves the condensation of amidines 1 with 1,3-dicarbonyl compounds 2 or their synthetic equivalents (Scheme 1a). Although the nature and reactivity profile of these C-C-C units have been widely explored, 2 the number of available methods incorporating an alkyne motive remains scarce 3 and these are mainly related with the use of ethynyl

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“…In the field of energetic materials, acetamidines are starting materials for synthesis of 2,2-dinitroethene-1,1,-diamine (Latypov et al , 1998; Jalový et al , 2013), the compound with reduced sensitivity to mechanical stimuli. Main reason for the use of acetamidine in the form of salts is that free base of acetamidine is hygroscopic and rather unstable producing ammonia and acetonitrile at elevated temperatures (Crossland and Grevil, 1981) or acetamidinium carbonate in contact with air (Norrestam, 1984).…”

Section: Introductionmentioning

confidence: 99%

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

Maixner

Kačer

2017

Powder Diffr.

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X-ray powder diffraction data, unit-cell parameters, and space group for acetamidinium formate, C3H8N2O2, are reported [a = 6.4564(5) Å, c = 13.021 (3) Å, unit-cell volume V = 542.8(3) Å3, M.p. = 215(1)°C, ρc = 1.274 g.cm−3, ρm = 1.269 g.cm−3, Z = 4, and space group P43212]. The front-loaded technique got sample with strong preferred orientation because of plate-like shape of crystallites, so the capillary packing was used for final powder data collection. All measured lines were indexed and are consistent with the P43212 space group. No detectable impurities were observed.

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A Convenient Preparation of Acetamidine.

Cited by 16 publications

References 0 publications

Molecular Isomer Identification of Titan’s Tholins Organic Aerosols by Photoelectron/Photoion Coincidence Spectroscopy Coupled to VUV Synchrotron Radiation

Molecular Isomer Identification of Titan’s Tholins Organic Aerosols by Photoelectron/Photoion Coincidence Spectroscopy Coupled to VUV Synchrotron Radiation

Synthesis of Fully Substituted Pyrimidines

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

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A Convenient Preparation of Acetamidine.

Cited by 16 publications

References 0 publications

Molecular Isomer Identification of Titan’s Tholins Organic Aerosols by Photoelectron/Photoion Coincidence Spectroscopy Coupled to VUV Synchrotron Radiation

Molecular Isomer Identification of Titan’s Tholins Organic Aerosols by Photoelectron/Photoion Coincidence Spectroscopy Coupled to VUV Synchrotron Radiation

Synthesis of Fully Substituted Pyrimidines

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

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Product

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