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Ethylenimine

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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
Deltafliquid91.90 ± 0.59kJ/molCcbNelson and Jessup, 1952 
Quantity Value Units Method Reference Comment
Deltacliquid-1591.36 ± 0.57kJ/molCcbNelson 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
Tboil328. - 329.KN/ABuckingham and Donaghy, 1982BS
Tboil328.65KN/AAnderson and Shimanskaya, 1969Uncertainty assigned by TRC = 0.6 K; TRC
Tboil329.KN/ASearles, Tamres, et al., 1956Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Tfus195.15KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.5 K; TRC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
57.0 ± 0.2288.CBernardes, Minas da Piedade, et al., 2007AC
34.9288.AStephenson and Malanowski, 1987Based on data from 274. - 303. K.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

1-Piperazineethanamine + Ethylenimine = N-[2-(1-piperazinyl)ethyl]ethylenediamine

By formula: C6H15N3 + C2H5N = C8H20N4

Quantity Value Units Method Reference Comment
Deltar87. ± 4.kJ/molCmDalin, Bobylev, et al., 1988liquid phase; solvent: Aqueous HCl; Kinetic

1,2-Ethanediamine, N-(2-aminoethyl)- + Ethylenimine = 1,2-Ethanediamine, N,N'-bis(2-aminoethyl)-

By formula: C4H13N3 + C2H5N = C6H18N4

Quantity Value Units Method Reference Comment
Deltar83.3 ± 4.2kJ/molCmDalin, Bobylev, et al., 1988liquid phase; solvent: Aqueous HCl; Kinetic

1,2-Ethanediamine, N,N'-bis(2-aminoethyl)- + Ethylenimine = Tetraethylenepentamine

By formula: C6H18N4 + C2H5N = C8H23N5

Quantity Value Units Method Reference Comment
Deltar83.3 ± 4.6kJ/molCmDalin, Bobylev, et al., 1988liquid phase; solvent: Aqueous HCl; Kinetic

Piperazine + Ethylenimine = 1-Piperazineethanamine

By formula: C4H10N2 + C2H5N = C6H15N3

Quantity Value Units Method Reference Comment
Deltar86. ± 2.kJ/molCmDalin, Bobylev, et al., 1988liquid phase; solvent: Aqueous HCl; Kinetic

Ethylenediamine + Ethylenimine = 1,2-Ethanediamine, N-(2-aminoethyl)-

By formula: C2H8N2 + C2H5N = C4H13N3

Quantity Value Units Method Reference Comment
Deltar82.8 ± 5.0kJ/molCmDalin, Bobylev, et al., 1988liquid 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)905.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity872.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.2 ± 0.1PEAue, Webb, et al., 1980LLK
9.3PEAue and Bowers, 1979LLK
9.52PEBodor, Dewar, et al., 1970RDSH
9.8EIKiser and Gallegos, 1962RDSH
9.94 ± 0.15EIGallegos and Kiser, 1961RDSH
9.85PEBieri, Asbrink, et al., 1982Vertical value; LBLHLM
9.85 ± 0.02PEYoshikawa, Hashimoto, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+15.5 ± 0.3?EIGallegos and Kiser, 1961RDSH
C2HN+18.1 ± 0.6?EIGallegos and Kiser, 1961RDSH
C2H2+16.4 ± 0.4?EIGallegos and Kiser, 1961RDSH
C2H2N+17.0 ± 0.2?EIGallegos and Kiser, 1961RDSH
C2H3+16.9 ± 0.3?EIGallegos and Kiser, 1961RDSH
C2H3N+15.2 ± 0.3?EIGallegos and Kiser, 1961RDSH
C2H4+13.3 ± 0.2NHEIGallegos and Kiser, 1961RDSH
C2H4N+12.2 ± 0.1HEIGallegos and Kiser, 1961RDSH
C2N+23.0 ± 0.4H2+3H?EIGallegos and Kiser, 1961RDSH

IR Spectrum

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Data compiled by: Coblentz Society, Inc.


Mass spectrum (electron ionization)

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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

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin E.GALLEGOS KANSAS STATE UNIVERSITY, MANHATTAN, KANSAS, USA
NIST MS number 18859

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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 sigma = 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(«nu»11)
a' 3 CH2 s-str 3015  D 3015 S gas 2999 VS p liq. OV(«nu»12)
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(«nu»2)
a 12 CH2 s-str 3015  D 3015 S gas 2999 VS p liq. OV(«nu»3)
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

VSVery strong
SStrong
MMedium
WWeak
VWVery weak
pPolarized
dpDepolarized
OVOverlapped by band indicated in parentheses.
C3~6 cm-1 uncertainty
D6~15 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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedPMS-100130.400.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPMS-100150.402.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedPEG-2000152.903.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000179.933.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, NIST Free 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]

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]

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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