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 thermochemistry 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 compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.32 | 50. | Thermodynamics Research Center, 1997 | Recommended values are in close agreement with those obtained from earlier statistical thermodynamics calculation [ Kilpatrick J.E., 1949]. |
35.99 | 100. | ||
40.82 | 150. | ||
46.31 | 200. | ||
55.67 | 273.15 | ||
59.03 | 298.15 | ||
59.28 | 300. | ||
72.09 | 400. | ||
83.00 | 500. | ||
92.07 | 600. | ||
99.73 | 700. | ||
106.3 | 800. | ||
112.0 | 900. | ||
117.0 | 1000. | ||
121.4 | 1100. | ||
125.2 | 1200. | ||
128.5 | 1300. | ||
131.4 | 1400. | ||
134.0 | 1500. |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
40.63 ± 0.16 | 148.2 | Kistiakowsky G.B., 1940 | Please also see Kistiakowsky G.B., 1940, 2. |
41.49 ± 0.17 | 157.8 | ||
47.53 ± 0.19 | 213.1 | ||
48.30 ± 0.19 | 218.4 | ||
49.02 ± 0.20 | 223.7 | ||
53.31 ± 0.21 | 258.0 | ||
55.23 ± 0.22 | 272.16 | ||
59.33 ± 0.24 | 300.00 | ||
63.81 ± 0.26 | 334.00 | ||
67.86 ± 0.27 | 366.45 |
Reaction thermochemistry data
Go To: Top, Gas phase 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 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° | 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 |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -295.1 ± 1.0 | kJ/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -298.2 ± 0.84 kJ/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° | 62. ± 15. | kJ/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° | 106. ± 10. | kJ/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° | 210. ± 9.2 | kJ/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° | -3.8 ± 2.1 | kJ/mol | Cm | Cordes and Gunzler, 1959 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -3.4 kJ/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° | 111. ± 39. | kJ/mol | Ther | Bartmess and Burnham, 1984 | gas phase; Between H2O, MeOH; B |
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 |
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 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Thermodynamics Research Center, 1997
Thermodynamics Research Center,
Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]
Kilpatrick J.E., 1949
Kilpatrick J.E.,
Heats, equilibrium constants, and free energies of formation of the C3 to C5 diolefins, styrene, and the methylstyrenes,
J. Res. Nat. Bur. Stand., 1949, 42, 225-240. [all data]
Kistiakowsky G.B., 1940
Kistiakowsky G.B.,
Gaseous heat capacities. II,
J. Chem. Phys., 1940, 8, 610-618. [all data]
Kistiakowsky G.B., 1940, 2
Kistiakowsky G.B.,
The low temperature gaseous heat capacities of certain C3 hydrocarbons,
J. Chem. Phys., 1940, 8, 970-977. [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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas 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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