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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Phase change 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:
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 | 240. ± 2. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 137.1 | K | N/A | Kistiakowsky, Ruhoff, et al., 1936 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 127. | K | N/A | Lespieau and Chavanne, 1905 | Uncertainty assigned by TRC = 10. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 136.59 | K | N/A | Pomerantz, Fookson, et al., 1954 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 394. | K | N/A | Tsonopoulos and Ambrose, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 52.5 | bar | N/A | Tsonopoulos and Ambrose, 1996 |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.6 | 259. | A | Stephenson and Malanowski, 1987 | Based on data from 136. to 274. K.; AC |
19.9 | 231. | A | Stephenson and Malanowski, 1987 | Based on data from 193. to 246. K.; AC |
21.3 | 223. | N/A | Stull, 1947 | Based on data from 153. to 238. K.; AC |
22.9 | 174. | N/A | Lamb and Roper, 1940 | Based on data from 138. to 189. K. See also Boublik, Fried, et al., 1984.; AC |
20.9 | 220. | MM | Livingston and Heisig, 1930 | Based on data from 203. to 236. K.; AC |
21.5 | 245. | N/A | Maass and Wright, 1921 | Based on data from 200. to 260. K. See also Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
152.5 to 238. | 3.79809 | 755.286 | -39.159 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Phase change 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) | 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 |
References
Go To: Top, Phase change 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.
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, 146-53. [all data]
Lespieau and Chavanne, 1905
Lespieau, R.; Chavanne, G.,
Liquefaction of Propadiene and Propyne.,
C. R. Hebd. Seances Acad. Sci., 1905, 140, 1035-1036. [all data]
Pomerantz, Fookson, et al., 1954
Pomerantz, P.; Fookson, A.; Mears, T.W.; Rothberg, S.; Howard, F.L.,
Synth. and Phys. Prop. of Several Aliphatic and Alicyclic Hydrocarbons hydrocarbons,
J. Res. Natl. Bur. Stand. (U. S.), 1954, 52, 59-65. [all data]
Tsonopoulos and Ambrose, 1996
Tsonopoulos, C.; Ambrose, D.,
Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons,
J. Chem. Eng. Data, 1996, 41, 645-656. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Lamb and Roper, 1940
Lamb, Arthur B.; Roper, Edwin E.,
The Vapor Pressures of Certain Unsaturated Hydrocarbons,
J. Am. Chem. Soc., 1940, 62, 4, 806-814, https://doi.org/10.1021/ja01861a032
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Livingston and Heisig, 1930
Livingston, Robert; Heisig, G.B.,
THE VAPOR PRESSURE OF ALLENE AS A FUNCTION OF TEMPERATURE,
J. Am. Chem. Soc., 1930, 52, 6, 2409-2410, https://doi.org/10.1021/ja01369a031
. [all data]
Maass and Wright, 1921
Maass, O.; Wright, C.H.,
SOME PHYSICAL PROPERTIES OF HYDROCARBONS CONTAINING TWO AND THREE CARBON ATOMS.,
J. Am. Chem. Soc., 1921, 43, 5, 1098-1111, https://doi.org/10.1021/ja01438a013
. [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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔrG° Free energy of reaction 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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