Ethylenimine
- Formula: C2H5N
- Molecular weight: 43.0678
- IUPAC Standard InChI: InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
- 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
View 3d structure (requires JavaScript / HTML 5) - 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 |
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
Vibrational and/or electronic energy levels
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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: 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 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | PMS-100 | 130. | 400. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
| Packed | PMS-100 | 150. | 402. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | PEG-2000 | 152. | 903. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
| Packed | PEG-2000 | 179. | 933. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, NIST Free Links, NIST Subscription Links, 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]
Shimanouchi, 1972
Shimanouchi, T.,
Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [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
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- Symbols used in this document:
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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