Ethylenimine

• Formula: C₂H₅N
• Molecular weight: 43.0678
• IUPAC Standard InChI: InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2 Copy

  
• IUPAC Standard InChIKey: NOWKCMXCCJGMRR-UHFFFAOYSA-N Copy
• CAS Registry Number: 151-56-4
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Aziridine; Azacyclopropane; Aziran; Dimethylenimine; Ethyleneimine; EI; Aethylenimin; Azirane; Aziridin; 1H-Azirine, dihydro-; Dihydroazirene; Dihydro-1H-azirine; Dimethyleneimine; ENT-50324; Ethyleenimine; Etilenimina; Rcra waste number P054; TL 337
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Phase change data

Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Gas phase ion energetics data

Go To: Top, Phase change data, Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₂H₅N⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

Gas Chromatography

Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Kovats' RI, polar column, isothermal

View large format table.

References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Anderson and Shimanskaya, 1969
Anderson, A.A.; Shimanskaya, M.V., Gas-Liquid Chromatography of some Aliphatic and Heterocyclic Polyfunctional Amines: II. Solution Thermodyn. of Amines in Fix. Phas., Latv. PSR Zinat. Akad. Vestis, Kim. Ser., 1969, No. 5, 527. [all data]

Searles, Tamres, et al., 1956
Searles, S.; Tamres, M.; Block, F.; Quarterman, L.A., Hydrogen Bonding and Basicity of Cyclic Imines, J. Am. Chem. Soc., 1956, 78, 4917-20. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Bernardes, Minas da Piedade, et al., 2007
Bernardes, Carlos E.S.; Minas da Piedade, Manuel E.; Amaral, Luísa M.P.F.; Ferreira, Ana I.M.C.L.; Ribeiro da Silva, Manuel A.V.; Diogo, Hermínio P.; Costa Cabral, Benedito J., Energetics of C-F, C-Cl, C-Br, and C-I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH ₂ CH ₂ OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical, J. Phys. Chem. A, 2007, 111, 9, 1713-1720, https://doi.org/10.1021/jp0675678 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Aue, Webb, et al., 1980
Aue, D.H.; Webb, H.M.; Davidson, W.R.; Vidal, M.; Bowers, M.T.; Goldwhite, H.; Vertal, L.E.; Douglas, J.E.; Kollman, P.A.; Kenyon, G.L., Proton affinities photoelectron spectra of three-membered-ring J. Heterocycl. Chem., J. Am. Chem. Soc., 1980, 102, 5151. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Jennings, W.B.; Worley, S.D., Photoelectron spectra of molecules-IV.Ionization potentials and heats of formation of some hydrazines and amines, Tetrahedron, 1970, 26, 4109. [all data]

Kiser and Gallegos, 1962
Kiser, R.W.; Gallegos, E.J., A technique for the rapid determination of ionization and appearance potentials, J. Phys. Chem., 1962, 66, 947. [all data]

Gallegos and Kiser, 1961
Gallegos, E.; Kiser, R.W., Electron impact spectroscopy of ethylene sulfide and ethylenimine, J. Phys. Chem., 1961, 65, 1177. [all data]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]

Yoshikawa, Hashimoto, et al., 1974
Yoshikawa, K.; Hashimoto, M.; Morishima, I., Photoelectron spectroscopic study of cyclic amines. The relation between ionization potentials, basicities, and s character of the nitrogen lone pair electrons, J. Am. Chem. Soc., 1974, 96, 288. [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.