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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Phase change data
Go To: Top, Gas phase ion energetics data, Vibrational and/or electronic energy levels, 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
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 (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.6 ± 0.05 | 288. | C | Bernardes, Minas da Piedade, et al., 2007 | AC |
8.34 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 274. to 303. K.; AC |
Gas phase ion energetics data
Go To: Top, Phase change data, Vibrational and/or electronic energy levels, 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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 216.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 208.5 | kcal/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 |
Vibrational and/or electronic energy levels
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: Takehiko Shimanouchi
Symmetry: Cs Symmetry Number σ = 1
Sym. | No | Approximate | Selected Freq. | Infrared | Raman | Comments | ||||
---|---|---|---|---|---|---|---|---|---|---|
Species | type of mode | Value | Rating | Value | Phase | Value | Phase | |||
a' | 1 | NH str | 3338 | C | 3338 W | gas | 3302 M p | liq. | ||
a' | 2 | CH2 a-str | 3079 | D | 3079 S | gas | 3059 M dp | liq. | OV(ν11) | |
a' | 3 | CH2 s-str | 3015 | D | 3015 S | gas | 2999 VS p | liq. | OV(ν12) | |
a' | 4 | CH2 scis | 1482 | C | 1482 W | gas | 1471 W p | liq. | ||
a' | 5 | Ring str | 1211 | C | 1211 S | gas | 1212 VS p | liq. | ||
a' | 6 | CH2 twist | 1095 | D | 1095 S | gas | 1088 W p | liq. | ||
a' | 7 | CH2 wag | 1090 | D | 1090 S | gas | 1088 W p | liq. | ||
a' | 8 | NH bend | 998 | C | 998 M | gas | 1028 W | liq. | ||
a' | 9 | Ring deform | 856 | C | 856 VS | gas | 855 M dp | liq. | ||
a' | 10 | CH2 rock | 773 | C | 773 S | gas | 787 W dp | liq. | ||
a | 11 | CH2 a-str | 3079 | D | 3079 S | gas | 3059 M dp | liq. | OV(ν2) | |
a | 12 | CH2 s-str | 3015 | D | 3015 S | gas | 2999 VS p | liq. | OV(ν3) | |
a | 13 | CH2 scis | 1463 | C | 1463 W | gas | 1452 W dp | liq. | ||
a | 14 | CH2 twist | 1268 | C | 1268 M | gas | 1276 VW | liq. | ||
a | 15 | NH bend | 1237 | C | 1237 M | gas | 1297 W p | liq. | ||
a | 16 | CH2 wag | 1131 | C | 1131 M | gas | 1130 VW | liq. | ||
a | 17 | Ring deform | 904 | C | 904 S | gas | ||||
a | 18 | CH2 rock | 817 | D | 817 M dp | liq. | ||||
Source: Shimanouchi, 1972
Notes
VS | Very strong |
S | Strong |
M | Medium |
W | Weak |
VW | Very weak |
p | Polarized |
dp | Depolarized |
OV | Overlapped by band indicated in parentheses. |
C | 3~6 cm-1 uncertainty |
D | 6~15 cm-1 uncertainty |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, 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]
Shimanouchi, 1972
Shimanouchi, T.,
Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, 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
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