Allene
- Formula: C3H4
- Molecular weight: 40.0639
- IUPAC Standard InChIKey: IYABWNGZIDDRAK-UHFFFAOYSA-N
- CAS Registry Number: 463-49-0
- 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: Propadiene; 1,2-Propadiene; sym-Allylene; Dimethylenemethane; CH2=C=CH2; Propa-1,2-diene
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Gas phase ion energetics data
Go To: Top, Ion clustering data, Mass spectrum (electron ionization), 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
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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 C3H4+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.692 ± 0.004 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 775.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 745.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.688 ± 0.002 | PE | Yang, Wang, et al., 1990 | LL |
10.06 | PE | Kimura, Katsumata, et al., 1981 | LLK |
9.691 ± 0.004 | PI | Stockbauer, McCulloh, et al., 1979 | LLK |
9.696 ± 0.002 | TE | Parr, Jason, et al., 1978 | LLK |
9.62 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.62 | EI | Lossing, 1972 | LLK |
10.017 ± 0.003 | S | Iverson and Russell, 1972 | LLK |
9.53 ± 0.03 | PI | Matthews and Warneck, 1969 | RDSH |
9.83 | PE | Dewar and Worley, 1969 | RDSH |
9.69 | PE | Baker and Turner, 1969 | RDSH |
9.62 ± 0.04 | PI | Parr and Elder, 1968 | RDSH |
10. | PE | Leng and Nyberg, 1977 | Vertical value; LLK |
10.2 ± 0.1 | PE | Bieri, Burger, et al., 1977 | Vertical value; LLK |
10.02 | PE | Thomas and Thompson, 1974 | Vertical value; LLK |
10.07 | PE | Brogli, Crandall, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H+ | 16.9 ± 0.1 | H2+H | TE | Parr, Jason, et al., 1978 | LLK |
C3H+ | 18.56 ± 0.05 | H2+H | EI | Franklin and Mogenis, 1967 | RDSH |
C3H2+ | 13.5 ± 0.2 | H2 | TE | Parr, Jason, et al., 1978 | LLK |
C3H2+ | 14.34 ± 0.08 | H2 | EI | Franklin and Mogenis, 1967 | RDSH |
C3H3+ | 11.60 ± 0.01 | H | PI | Stockbauer and Rosenstock, 1978 | LLK |
C3H3+ | 11.48 ± 0.02 | ? | TE | Parr, Jason, et al., 1978 | LLK |
C3H3+ | 11.47 | H | EI | Lossing, 1972 | LLK |
C3H3+ | 11.48 | H | PI | Matthews and Warneck, 1969 | RDSH |
C3H3+ | 11.48 ± 0.02 | H | PI | Parr and Elder, 1968 | RDSH |
C3H22+ | 32.5 ± 0.2 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
De-protonation reactions
C3H3- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1590. ± 8.4 | kJ/mol | D-EA | Robinson, Polak, et al., 1995 | gas phase; Neutral acid: allene. Propyne would be 1.0 kcal/mol less acidic.; B |
ΔrH° | 1596. ± 13. | kJ/mol | G+TS | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0; kinetic scheme factors in isomerization; B |
ΔrH° | 1592. ± 8.8 | kJ/mol | D-EA | Oakes and Ellison, 1983 | gas phase; Neutral acid: allene. Propyne would be 1.0 kcal/mol less acidic.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1560. ± 13. | kJ/mol | IMRE | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0; kinetic scheme factors in isomerization; B |
ΔrG° | 1556. ± 9.2 | kJ/mol | H-TS | Oakes and Ellison, 1983 | gas phase; Neutral acid: allene. Propyne would be 1.0 kcal/mol less acidic.; B |
Ion clustering data
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
RCD - Robert C. Dunbar
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: Cr+ + C3H4 = (Cr+ • C3H4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 176. ± 8.4 | kJ/mol | CIDT | Fisher and Armentrout, 1992 | propyne or allene; RCD |
By formula: Rh+ + C3H4 = (Rh+ • C3H4)
Enthalpy of reaction
ΔrH° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
222. (+19.,-0.) | CID | Chen and Armetrout, 1995 | gas phase; guided ion beam CID; M |
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, Ion clustering 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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. |
---|---|
NIST MS number | 45 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), 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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | CP Sil 5 CB | 20. | 329.5 | Do and Raulin, 1992 | 25. m/0.15 mm/2. μm, H2 |
Capillary | PoraPLOT Q | 100. | 311. | Do and Raulin, 1989 | 10. m/0.32 mm/10. μm, H2 |
Capillary | PoraPLOT Q | 160. | 316. | Do and Raulin, 1989 | 10. m/0.32 mm/10. μm, H2 |
Packed | Squalane | 27. | 317. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 318. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 319. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 320. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 26. | 336. | Zulaïca and Guiochon, 1966 | Column length: 10. m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 326. | Hoekman, 1993 | 60. m/0.32 mm/1.0 μm, He; Program: -40 C for 12 min; -40 - 125 C at 3 deg.min; 125-185 C at 6 deg/min; 185 - 220 C at 20 deg/min; hold 220 C for 2 min |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 326. | Bramston-Cook, 2013 | 60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min |
Capillary | Petrocol DH | 337. | Supelco, 2012 | 100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min |
References
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Yang, Wang, et al., 1990
Yang, Z.Z.; Wang, L.S.; Lee, Y.T.; Shirley, D.A.; Huang, S.Y.; Lester, W.A., Jr.,
Molecular beam photoelectron spectroscopy of allene,
Chem. Phys. Lett., 1990, 171, 9. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Stockbauer, McCulloh, et al., 1979
Stockbauer, R.; McCulloh, K.E.; Parr, A.C.,
The ionization potential of allene,
Int. J. Mass Spectrom. Ion Phys., 1979, 31, 187. [all data]
Parr, Jason, et al., 1978
Parr, A.C.; Jason, A.J.; Stockbauer, R.,
Photoionization and threshold photoelectron-photoion coincidence study of allene from onset to 20eV,
Int. J. Mass Spectrom. Ion Phys., 1978, 26, 23. [all data]
Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P.,
Valence ionization enrgies of hydrocarbons,
Helv. Chim. Acta, 1977, 60, 2213. [all data]
Lossing, 1972
Lossing, F.P.,
Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C3H3, C3H5, and C4H7 radicals and ions,
Can. J. Chem., 1972, 50, 3973. [all data]
Iverson and Russell, 1972
Iverson, A.A.; Russell, B.R.,
A medium resolution study of allene in the vacuum ultraviolet. I. Spectra and a preliminary ionization potential,
Spectrochim. Acta Part A, 1972, 28, 447. [all data]
Matthews and Warneck, 1969
Matthews, C.S.; Warneck, P.,
Heats of formation of CHO+ and C3H3+ by photoionization,
J. Chem. Phys. 5, 1969, 1, 854. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Baker and Turner, 1969
Baker, C.; Turner, D.W.,
Photoelectron spectra of allene and keten; Jahn-Teller distortion in the ionisation of allene,
Chem. Commun., 1969, 480. [all data]
Parr and Elder, 1968
Parr, A.C.; Elder, F.A.,
Photoionization of 1,3butadiene, 1,2-butadiene, allene, and propyne,
J. Chem. Phys., 1968, 49, 2659. [all data]
Leng and Nyberg, 1977
Leng, F.J.; Nyberg, G.L.,
Angular-distribution He(I)/Ne(I) photoelectron spectra of allene,
J. Chem. Soc. Faraday Trans. 2, 1977, 73, 1719. [all data]
Thomas and Thompson, 1974
Thomas, R.K.; Thompson, H.,
The photoelectron spectra of allene, deuteroallenes and tetrafluoroallene,
Proc. R. Soc. London A:, 1974, 339, 29. [all data]
Brogli, Crandall, et al., 1973
Brogli, F.; Crandall, J.K.; Heilbronner, E.; Kloster-Jensen, E.; Sojka, S.A.,
The photoelectron spectra of methyl-substituted allenes and of tetramethyl-bisallenyl,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 455. [all data]
Franklin and Mogenis, 1967
Franklin, J.L.; Mogenis, A.,
An electron impact study of ions from several dienes,
J. Phys. Chem., 1967, 71, 2820. [all data]
Stockbauer and Rosenstock, 1978
Stockbauer, R.; Rosenstock, H.M.,
Kinetic shift in methane allene ion fragmentation,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 185. [all data]
Robinson, Polak, et al., 1995
Robinson, M.S.; Polak, M.L.; Bierbaum, V.M.; DePuy, C.H.; Lineberger, W.C.,
Experimental Studies of Allene, Methylacetylene, and the Propargyl Radical: Bond Dissociation Energies, Gas-Phase Acidities, and Ion-Molecule Chemistry,
J. Am. Chem. Soc., 1995, 117, 25, 6766, https://doi.org/10.1021/ja00130a017
. [all data]
Oakes and Ellison, 1983
Oakes, J.M.; Ellison, B.G.,
Photoelectron spectroscopy of the allenyl anion CH2=C=CH-,
J. Am. Chem. Soc., 1983, 105, 2969. [all data]
Fisher and Armentrout, 1992
Fisher, E.R.; Armentrout, P.B.,
Activation of Alkanes by Cr+: Unique Reactivity of Ground-State Cr+(6S) and Thermochemistry of Neutral and Ionic Chromium-Carbon Bonds,
J. Am. Chem. Soc., 1992, 114, 6, 2039, https://doi.org/10.1021/ja00032a017
. [all data]
Chen and Armetrout, 1995
Chen, Y.M.; Armetrout, P.B.,
Activation of C2H6, C3H8, and c-C3H6 by Gas-Phase Rh+ and the Thermochemistry of Rh-Ligand Complexes,
J. Am. Chem. Soc., 1995, 117, 36, 9291, https://doi.org/10.1021/ja00141a022
. [all data]
Do and Raulin, 1992
Do, L.; Raulin, F.,
Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column,
J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R
. [all data]
Do and Raulin, 1989
Do, L.; Raulin, F.,
Gas chromatography of Titan's atmosphere. I. Analysis of low-molecular-weight hydrocarbons and nitriles with a PoraPLOT Q porous polymer coated open-tubular capillary column,
J. Chromatogr., 1989, 481, 45-54, https://doi.org/10.1016/S0021-9673(01)96751-2
. [all data]
Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203
. [all data]
Zulaïca and Guiochon, 1966
Zulaïca, J.; Guiochon, G.,
Analyse des hauts polymères par chromatographie en phase gazeuse de leurs produits de pyrolyse. II. Application à quelques hydrocarbures macromoléculaires purs,
Bull. Soc. Chim. Fr., 1966, 4, 1351-1363. [all data]
Hoekman, 1993
Hoekman, S.K.,
Improved gas chromatography procedure for speciated hydrocarbon measurements of vehicle emissions,
J. Chromatogr., 1993, 639, 2, 239-253, https://doi.org/10.1016/0021-9673(93)80260-F
. [all data]
Bramston-Cook, 2013
Bramston-Cook, R.,
Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]
Supelco, 2012
Supelco, CatalogNo. 24160-U,
Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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