Vinylamine

Structural formula
General
Surname	Vinylamine
other names	Aminoethene; Aminoethylene; Ethenamine ( IUPAC ) ;
Molecular formula	C 2 H 5 N
External identifiers / databases
EC number	209-802-7
ECHA InfoCard	100.008.913
PubChem	11642
Wikidata	Q910511
properties
Molar mass	43.07 g mol −1
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vinylamine , also known as aminoethene , aminoethylene or ethenamine , is an amine with the chemical formula C ₂ H ₅ N or H ₂ C = CH — NH ₂ .

Manufacture and properties

Imine-enamine tautomerism of vinylamine

Vinylamine exists as a tautomer of ethylidenimine . Both tautomers, the enamine vinylamine and the corresponding imine ethylidenimine, are unstable. Ethylidenimine can be briefly synthesized in the gas phase , for example as a rearrangement or decomposition product of aziridine or 2,4,6-trimethyl- [1,3,5] triazine.

Vinylamine is the theoretical base monomer of polyvinylamine (PVAm). However, the synthesis of PVAm takes place via the polymerization of N -vinylformamide with subsequent hydrolysis , since vinylamine itself is not accessible.

Individual evidence

↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of vinylamines in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was retrieved on July 28, 2019, is reproduced from a self-classification by the distributor .
↑ I. Stolkin, T.-K. Ha, Hs.H. Günthard: N-methylmethyleneimine and ethylideneimine: Gas- and matrix-infrared spectra, AB initio calculations and thermodynamic properties . In: Chemical Physics . tape 21 , no. 3 , May 1977, pp. 327-347 , doi : 10.1016 / 0301-0104 (77) 85189-6 .

literature

D. Mcnaughton, EG Robertson: The Far-Infrared Inversion Transition of Vinylamine. In: Journal of Molecular Spectroscopy 163/1994, pp. 80-85; doi: 10.1006 / jmsp.1994.1009 .
S. Saebo¸, L. Radom: The structure of vinylamine. In: Journal of Molecular Structure : THEOCHEM 89/1982, pp. 227-233; doi: 10.1016 / 0166-1280 (82) 80080-8 .
SF Dyke: The Chemistry of Enamines , Cambridge University Press, London, 1973.
Frank J. Lovas, Frank O. Clark: Pyrolysis of Ethylamine. I. Microwave Spectrum and Molecular Constants of Vinylamine. In: J. Chem. Phys. 62/1975, p. 1925; doi: 10.1063 / 1.430679 .
R. Meyer: The Inversion of the Amino Group in Vinylamine, a Flexible Model Treatment. In: Helvetica Chimica Acta 61/1978, pp. 1418-1426; doi: 10.1002 / hlca.19780610426 .
MR Ellenberger, RA Eades, MW Thomsen, WE Farneth, DA Dixon: Proton affinities of ethylidenimine and vinylamine. In: J. Am. Chem. Soc. 101/1979, pp. 7151-7154; doi: 10.1021 / ja00518a003 .
Carlos N. Sanramé, Gustavo A. Argüello, Adriana B. Pierini: Evaluation of reactive and nonreactive paths for the interaction between ¹ O ₂ ( ¹ Δ _g ) and vinylamine using semiempirical methods. In: Journal of Molecular Structure: THEOCHEM 367/1996, pp. 119-126; doi: 10.1016 / S0166-1280 (96) 04551-4 .

Web links

Ethenylamine Landolt-Börnstein, University of Hamburg

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of vinylamines in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was retrieved on July 28, 2019, is reproduced from a self-classification by the distributor .

[2] I. Stolkin, T.-K. Ha, Hs.H. Günthard: N-methylmethyleneimine and ethylideneimine: Gas- and matrix-infrared spectra, AB initio calculations and thermodynamic properties . In: Chemical Physics . tape 21 , no. 3 , May 1977, pp. 327-347 , doi : 10.1016 / 0301-0104 (77) 85189-6 .