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Synthesis and properties of acetamidinium salts.

Jalový Z, Matyáš R, Ottis J, Růžička A, Simůnek P, Polášek M - Chem Cent J (2011)

Bottom Line: Acetamidines 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 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.

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Affiliation: University of Pardubice, Faculty of Chemical Technology, Institute of Energetic Materials, Studentská 95, CZ-532 10 Pardubice, Czech Republic. zdenek.jalovy@upce.cz.

ABSTRACT

Background: Acetamidines 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.

Results: Acetamidinium 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.

Conclusions: The 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.

No MeSH data available.


Related in: MedlinePlus

Preparation of acetamidinium nitrate (2), sulphate (5) and oxalate (7) from 1.
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Figure 2: Preparation of acetamidinium nitrate (2), sulphate (5) and oxalate (7) from 1.

Mentions: The procedure for the preparation of acetamidinium sulphate (5) via an ion exchange reaction from acetamidinium chloride (1) was earlier described by us [22]. This procedure was now used for the synthesis of the nitrate (2) and the oxalate (7). Thus, it may be considered as a universal method for the preparation of acetamidine salts starting from 1 (Figure 2).


Synthesis and properties of acetamidinium salts.

Jalový Z, Matyáš R, Ottis J, Růžička A, Simůnek P, Polášek M - Chem Cent J (2011)

Preparation of acetamidinium nitrate (2), sulphate (5) and oxalate (7) from 1.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3275501&req=5

Figure 2: Preparation of acetamidinium nitrate (2), sulphate (5) and oxalate (7) from 1.
Mentions: The procedure for the preparation of acetamidinium sulphate (5) via an ion exchange reaction from acetamidinium chloride (1) was earlier described by us [22]. This procedure was now used for the synthesis of the nitrate (2) and the oxalate (7). Thus, it may be considered as a universal method for the preparation of acetamidine salts starting from 1 (Figure 2).

Bottom Line: Acetamidines 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 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: University of Pardubice, Faculty of Chemical Technology, Institute of Energetic Materials, Studentská 95, CZ-532 10 Pardubice, Czech Republic. zdenek.jalovy@upce.cz.

ABSTRACT

Background: Acetamidines 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.

Results: Acetamidinium 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.

Conclusions: The 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.

No MeSH data available.


Related in: MedlinePlus