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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Reaction thermochemistry data
Go To: Top, 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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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
C3H3- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 380.0 ± 2.0 | kcal/mol | D-EA | Robinson, Polak, et al., 1995 | gas phase; Neutral acid: allene. Propyne would be 1.0 kcal/mol less acidic.; B |
ΔrH° | 381.4 ± 3.1 | kcal/mol | G+TS | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0; kinetic scheme factors in isomerization; B |
ΔrH° | 380.6 ± 2.1 | kcal/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° | 372.8 ± 3.0 | kcal/mol | IMRE | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0; kinetic scheme factors in isomerization; B |
ΔrG° | 372.0 ± 2.2 | kcal/mol | H-TS | 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 |
---|---|---|---|---|---|
ΔrH° | -70.54 ± 0.25 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -71.28 ± 0.20 kcal/mol; At 355 °K; ALS |
(CAS Reg. No. 86046-90-4 • 4294967295) +
= CAS Reg. No. 86046-90-4
By formula: (CAS Reg. No. 86046-90-4 • 4294967295C3H4) + C3H4 = CAS Reg. No. 86046-90-4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 14.8 ± 3.7 | kcal/mol | Ther | Bartmess and Burnham, 1984 | gas phase; value altered from reference due to change in acidity scale; B |
(CAS Reg. No. 83268-51-3 • 4294967295) +
= CAS Reg. No. 83268-51-3
By formula: (CAS Reg. No. 83268-51-3 • 4294967295C3H4) + C3H4 = CAS Reg. No. 83268-51-3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 25.4 ± 2.4 | kcal/mol | N/A | Bartmess and Burnham, 1984 | gas phase; value altered from reference due to change in acidity scale; B |
(CAS Reg. No. 1724-46-5 • 4294967295) +
= CAS Reg. No. 1724-46-5
By formula: (CAS Reg. No. 1724-46-5 • 4294967295C3H4) + C3H4 = CAS Reg. No. 1724-46-5
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50.2 ± 2.2 | kcal/mol | N/A | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: C3H4 = C3H4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.90 ± 0.50 | kcal/mol | Cm | Cordes and Gunzler, 1959 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -0.81 kcal/mol; ALS |
(CAS Reg. No. 86046-88-0 • 4294967295) +
= CAS Reg. No. 86046-88-0
By formula: (CAS Reg. No. 86046-88-0 • 4294967295C3H4) + C3H4 = CAS Reg. No. 86046-88-0
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 26.6 ± 9.4 | kcal/mol | Ther | Bartmess and Burnham, 1984 | gas phase; Between H2O, MeOH; B |
By formula: Rh+ + C3H4 = (Rh+ • C3H4)
Enthalpy of reaction
ΔrH° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
53.0 (+4.6,-0.) | CID | Chen and Armetrout, 1995 | gas phase; guided ion beam CID; M |
By formula: Cr+ + C3H4 = (Cr+ • C3H4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 42.0 ± 2.0 | kcal/mol | CIDT | Fisher and Armentrout, 1992 | propyne or allene; RCD |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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) | 185.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 178.3 | kcal/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° | 380.0 ± 2.0 | kcal/mol | D-EA | Robinson, Polak, et al., 1995 | gas phase; Neutral acid: allene. Propyne would be 1.0 kcal/mol less acidic.; B |
ΔrH° | 381.4 ± 3.1 | kcal/mol | G+TS | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0; kinetic scheme factors in isomerization; B |
ΔrH° | 380.6 ± 2.1 | kcal/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° | 372.8 ± 3.0 | kcal/mol | IMRE | Robinson, Polak, et al., 1995 | gas phase; Relative to MeOH at 375.0; kinetic scheme factors in isomerization; B |
ΔrG° | 372.0 ± 2.2 | kcal/mol | H-TS | Oakes and Ellison, 1983 | gas phase; Neutral acid: allene. Propyne would be 1.0 kcal/mol less acidic.; B |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene,
J. Am. Chem. Soc., 1936, 58, 146-153. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Bartmess and Burnham, 1984
Bartmess, J.E.; Burnham, R.,
Effect of central substituents on the gas phase acidities of propenes,
J. Org. Chem., 1984, 49, 1382. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Cordes and Gunzler, 1959
Cordes, J.F.; Gunzler, H.,
Das propin/propadien-gleichgewicht,
Chem. Ber., 1959, 92, 1055-1062. [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]
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]
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]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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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