Ethylenimine
- Formula: C2H5N
- Molecular weight: 43.0678
- IUPAC Standard InChIKey: NOWKCMXCCJGMRR-UHFFFAOYSA-N
- 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
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Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 91.90 ± 0.59 | kJ/mol | Ccb | Nelson and Jessup, 1952 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1591.36 ± 0.57 | kJ/mol | Ccb | Nelson and Jessup, 1952 |
Phase change data
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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 328. to 329. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 328.65 | K | N/A | Anderson and Shimanskaya, 1969 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tboil | 329. | K | N/A | Searles, Tamres, et al., 1956 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 195.15 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.5 K; TRC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
57.0 ± 0.2 | 288. | C | Bernardes, Minas da Piedade, et al., 2007 | AC |
34.9 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 274. to 303. K.; AC |
Reaction thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
By formula: C6H15N3 + C2H5N = C8H20N4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 87. ± 4. | kJ/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic |
By formula: C4H13N3 + C2H5N = C6H18N4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 83.3 ± 4.2 | kJ/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic |
By formula: C6H18N4 + C2H5N = C8H23N5
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 83.3 ± 4.6 | kJ/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic |
By formula: C4H10N2 + C2H5N = C6H15N3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 86. ± 2. | kJ/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic |
By formula: C2H8N2 + C2H5N = C4H13N3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82.8 ± 5.0 | kJ/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic |
Gas phase ion energetics data
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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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 905.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 872.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.2 ± 0.1 | PE | Aue, Webb, et al., 1980 | LLK |
9.3 | PE | Aue and Bowers, 1979 | LLK |
9.52 | PE | Bodor, Dewar, et al., 1970 | RDSH |
9.8 | EI | Kiser and Gallegos, 1962 | RDSH |
9.94 ± 0.15 | EI | Gallegos and Kiser, 1961 | RDSH |
9.85 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.85 ± 0.02 | PE | Yoshikawa, Hashimoto, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 15.5 ± 0.3 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2HN+ | 18.1 ± 0.6 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H2+ | 16.4 ± 0.4 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H2N+ | 17.0 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H3+ | 16.9 ± 0.3 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H3N+ | 15.2 ± 0.3 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H4+ | 13.3 ± 0.2 | NH | EI | Gallegos and Kiser, 1961 | RDSH |
C2H4N+ | 12.2 ± 0.1 | H | EI | Gallegos and Kiser, 1961 | RDSH |
C2N+ | 23.0 ± 0.4 | H2+3H? | EI | Gallegos and Kiser, 1961 | RDSH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- GAS (80 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Nelson and Jessup, 1952
Nelson, R.A.; Jessup, R.S.,
Heats of combustion and formation of liquid ethylenimine,
J. Res. NBS, 1952, 48, 206-208. [all data]
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]
Dalin, Bobylev, et al., 1988
Dalin, A.R.; Bobylev, V.A.; Suslikov, V.F.; Kamskaya, O.I.; Tereshchenko, G.F.,
Nucleophilic cleavage and the formation of saturated heterocycles. VII. Kinetic and thermochemical study of reactions of aziridine with ethylene amines,
J. Gen. Chem. USSR, 1988, 58, 1868-1871. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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