Propene
- Formula: C3H6
- Molecular weight: 42.0797
- IUPAC Standard InChIKey: QQONPFPTGQHPMA-UHFFFAOYSA-N
- CAS Registry Number: 115-07-1
- 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. - Isotopologues:
- Other names: Propylene; 1-Propene; Methylethylene; 1-Propylene; CH3CH=CH2; Methylethene; NCI-C50077; UN 1077; R 1270
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Reaction thermochemistry data
Go To: Top, 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
C3H5- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 391.10 ± 0.30 | kcal/mol | G+TS | Ellison, Davico, et al., 1996 | gas phase; calculated dSacid=24.2±1.0 eu; B |
ΔrH° | 390.5 ± 1.0 | kcal/mol | D-EA | Wenthold, Polak, et al., 1996 | gas phase; B |
ΔrH° | 390.7 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 390.25 ± 0.65 | kcal/mol | G+TS | Mackay, Lien, et al., 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 383.80 ± 0.10 | kcal/mol | IMRE | Ellison, Davico, et al., 1996 | gas phase; calculated dSacid=24.2±1.0 eu; B |
ΔrG° | 383.9 ± 1.1 | kcal/mol | H-TS | Wenthold, Polak, et al., 1996 | gas phase; B |
ΔrG° | 384.1 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 383.60 ± 0.50 | kcal/mol | IMRE | Mackay, Lien, et al., 1978 | gas phase; B |
By formula: HBr + C3H6 = C3H7Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -20.43 | kcal/mol | Cm | Lacher, Kianpour, et al., 1957 | gas phase; ALS |
ΔrH° | -20.050 | kcal/mol | Cm | Lacher, Lea, et al., 1950 | gas phase; Heat of hydrobromination at 367°K; ALS |
ΔrH° | -20.10 ± 0.14 | kcal/mol | Cm | Lacher, Walden, et al., 1950 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -20.17 ± 0.24 kcal/mol; Heat of hydrobromination; ALS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -29.5 ± 1.2 | kcal/mol | Chyd | Kistiakowsky and Nickle, 1951 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -29.85 ± 0.50 kcal/mol; ALS |
ΔrH° | -29.87 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1935 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -30.115 ± 0.013 kcal/mol; At 355 °K; ALS |
C3H5- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 405.8 ± 2.0 | kcal/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrH° | >404.75 ± 0.60 | kcal/mol | G+TS | Froelicher, Freiser, et al., 1986 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 398.0 ± 2.1 | kcal/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrG° | >397.00 | kcal/mol | IMRB | Froelicher, Freiser, et al., 1986 | gas phase; B |
By formula: HI + C3H5I = C3H6 + I2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.96 ± 0.33 | kcal/mol | Eqk | Rodgers, Golden, et al., 1966 | gas phase; ALS |
ΔrH° | -9.5 ± 1.0 | kcal/mol | Eqk | Rodgers, Golden, et al., 1966 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -8.33 ± 0.23 kcal/mol; At 527 K; ALS |
By formula: C3H7Cl = C3H6 + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.3 ± 0.2 | kcal/mol | Eqk | Noren and Sunner, 1970 | gas phase; ALS |
ΔrH° | 17.62 ± 0.15 | kcal/mol | Eqk | Kabo and Andreevskii, 1963 | gas phase; At 415.5 K; ALS |
ΔrH° | 17.45 ± 0.50 | kcal/mol | Eqk | Howlett, 1955 | gas phase; ALS |
By formula: Co+ + C3H6 = (Co+ • C3H6)
Enthalpy of reaction
ΔrH° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
43.0 (+1.7,-0.) | CID | Armentrout and Kickel, 1994 | gas phase; guided ion beam CID; M | |
43.1 (+1.6,-0.) | CID | Haynes and Armentrout, 1994 | gas phase; guided ion beam CID; M |
By formula: C3H9Si+ + C3H6 = (C3H9Si+ • C3H6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 30.6 | kcal/mol | PHPMS | Li and Stone, 1989 | gas phase; condensation; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 42.5 | cal/mol*K | PHPMS | Li and Stone, 1989 | gas phase; condensation; M |
By formula: C3H6 + Br2 = C3H6Br2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -29.27 ± 0.20 | kcal/mol | Cm | Conn, Kistiakowsky, et al., 1938 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -29.41 ± 0.20 kcal/mol; At 355 °K; ALS |
C3H5- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | >404.75 ± 0.90 | kcal/mol | G+TS | Froelicher, Freiser, et al., 1986 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | >397.00 | kcal/mol | IMRB | Froelicher, Freiser, et al., 1986 | gas phase; B |
By formula: Li+ + C3H6 = (Li+ • C3H6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 23. | kcal/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: Rh+ + C3H6 = (Rh+ • C3H6)
Enthalpy of reaction
ΔrH° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
28.1 | CID | Chen and Armetrout, 1995 | gas phase; ΔrH>=, guided ion beam CID; M |
By formula: Fe+ + C3H6 = (Fe+ • C3H6)
Enthalpy of reaction
ΔrH° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
34.7 (+1.7,-0.) | CID | Armentrout and Kickel, 1994 | gas phase; guided ion beam CID; M |
(CAS Reg. No. 25012-80-0 • 4294967295) + = CAS Reg. No. 25012-80-0
By formula: (CAS Reg. No. 25012-80-0 • 4294967295C3H6) + C3H6 = CAS Reg. No. 25012-80-0
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 10.8 ± 2.1 | kcal/mol | N/A | DePuy, Gronert, et al., 1989 | gas phase; B |
(CAS Reg. No. 59513-13-2 • 4294967295) + = CAS Reg. No. 59513-13-2
By formula: (CAS Reg. No. 59513-13-2 • 4294967295C3H6) + C3H6 = CAS Reg. No. 59513-13-2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 14.6 ± 2.1 | kcal/mol | N/A | DePuy, Gronert, et al., 1989 | gas phase; B |
By formula: C3H6 + HCl = C3H7Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -17.54 | kcal/mol | Eqk | Kabo and Andreevskii, 1963 | gas phase; At 385°K; ALS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -20.62 | kcal/mol | Eqk | Furuyama, Golden, et al., 1969 | gas phase; ALS |
By formula: C3H6 + H2O4S = isopropyl hydrogen sulphate
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -9.2 ± 0.2 | kcal/mol | Eqk | Entelis, Korovina, et al., 1960 | liquid phase; ALS |
By formula: C3H6I2 = C3H6 + I2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 11.2 ± 0.4 | kcal/mol | Eqk | Benson and Amano, 1962 | gas phase; ALS |
By formula: C3H7Br = HBr + C3H6
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 19.3 ± 0.5 | kcal/mol | Eqk | Rozhnov and Andreevskii, 1962 | gas phase; ALS |
By formula: C3H6 + C3F6O = C6H6F6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -18.7 ± 1.0 | kcal/mol | Eqk | Moore, 1971 | gas phase; ALS |
By formula: Au+ + C3H6 = (Au+ • C3H6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | >75. | kcal/mol | IMRB | Schroeder, Hrusak, et al., 1995 | RCD |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Ellison, Davico, et al., 1996
Ellison, G.B.; Davico, G.E.; Bierbaum, V.M.; DePuy, C.H.,
Thermochemistry of theb Benzyl and Allyl Radicals and Ions,
Int. J. Mass Spectrom. Ion Proc., 1996, 156, 1-2, 109-131, https://doi.org/10.1016/S0168-1176(96)04383-2
. [all data]
Wenthold, Polak, et al., 1996
Wenthold, P.G.; Polak, M.L.; Lineberger, W.C.,
Photoelectron Spectroscopy of the Allyl and 2-Methylallyl Anions,
J. Phys. Chem., 1996, 100, 17, 6920, https://doi.org/10.1021/jp953401n
. [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]
Mackay, Lien, et al., 1978
Mackay, G.I.; Lien, M.H.; Hopkinson, A.C.; Bohme, D.K.,
Experimental and theoretical studies of proton removal from propene,
Can. J. Chem., 1978, 56, 131. [all data]
Lacher, Kianpour, et al., 1957
Lacher, J.R.; Kianpour, A.; Park, J.D.,
Reaction heats of organic halogen compounds. X. Vapor phase heats of hydrobromination of cyclopropane and propylene,
J. Phys. Chem., 1957, 61, 1124-1125. [all data]
Lacher, Lea, et al., 1950
Lacher, J.R.; Lea, K.R.; Walden, C.H.; Olson, G.G.; Park, J.D.,
Reaction heats of organic fluorine compounds. III. The vapor phase heats of hydrobromination of some simple fluoroolefins,
J. Am. Chem. Soc., 1950, 72, 3231-3234. [all data]
Lacher, Walden, et al., 1950
Lacher, J.R.; Walden, C.H.; Lea, K.R.; Park, J.D.,
Vapor phase heats of hydrobromination of cyclopropane and propylene,
J. Am. Chem. Soc., 1950, 72, 331-333. [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]
Kistiakowsky and Nickle, 1951
Kistiakowsky, G.B.; Nickle, A.G.,
Ethane-ethylene and propane-propylene equilibria,
Faraday Discuss. Chem. Soc., 1951, 10, 175-187. [all data]
Kistiakowsky, Ruhoff, et al., 1935
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. II. Hydrogenation of some simpler olefinic hydrocarbons,
J. Am. Chem. Soc., 1935, 57, 876-882. [all data]
DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R.,
The Gas Phase Acidities of the Alkanes,
J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003
. [all data]
Froelicher, Freiser, et al., 1986
Froelicher, S.W.; Freiser, B.S.; Squires, R.R.,
The C3H5- isomers. Experimental and theoretical studies of the tautomeric propenyl ions and the cyclopropyl anion in the gas phase,
J. Am. Chem. Soc., 1986, 108, 2853. [all data]
Rodgers, Golden, et al., 1966
Rodgers, A.S.; Golden, D.M.; Benson, S.W.,
The thermochemistry of the gas phase equilibrium I2 + C3H6 = C3H5I + HI,
J. Am. Chem. Soc., 1966, 88, 3194-3196. [all data]
Noren and Sunner, 1970
Noren, I.; Sunner, S.,
The enthalpy of formation of 2-chloropropane from equilibrium studies,
J. Chem. Thermodyn., 1970, 2, 597-602. [all data]
Kabo and Andreevskii, 1963
Kabo, G.Ya.; Andreevskii, D.N.,
Equilibrium of 2-chloropropane dehydrochlorination,
Neftekhimiya, 1963, 3, 764-770. [all data]
Howlett, 1955
Howlett, K.E.,
The use of equilibrium constants to calculate thermodynamic quantities. Part II,
J. Chem. Soc., 1955, 1784-17. [all data]
Armentrout and Kickel, 1994
Armentrout, P.B.; Kickel, B.L.,
Gas Phase Thermochemistry of Transition Metal Ligand Systems: Reassessment of Values and Periodic Trends, in Organometallic Ion Chemistry, B. S. Freiser, ed, 1994. [all data]
Haynes and Armentrout, 1994
Haynes, C.L.; Armentrout, P.B.,
Thermochemistry and Structures of CoC3H6+: Metallacyclic and Metal-Alkene Isomers,
Organomettalics, 1994, 13, 9, 3480, https://doi.org/10.1021/om00021a022
. [all data]
Li and Stone, 1989
Li, X.; Stone, J.A.,
Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes,
J. Am. Chem. Soc., 1989, 111, 15, 5586, https://doi.org/10.1021/ja00197a013
. [all data]
Conn, Kistiakowsky, et al., 1938
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A.,
Heats of organic reactions. VII. Addition of halogens to olefins,
J. Am. Chem. Soc., 1938, 60, 2764-2771. [all data]
Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L.,
Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases,
J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050
. [all data]
Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P.,
Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,
J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013
. [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]
Furuyama, Golden, et al., 1969
Furuyama, S.; Golden, D.M.; Benson, S.W.,
Thermochemistry of the gas phase equilibria i-C3H7I = C3H6 + HI, n-C3H7I = i-C3H7I, and C3H6 + 2HI = C3H8 + I2,
J. Chem. Thermodyn., 1969, 1, 363-375. [all data]
Entelis, Korovina, et al., 1960
Entelis, S.G.; Korovina, G.V.; Chirkov, N.M.,
The thermodynamics of propylene absorption by the H2SO4-H20 system,
Dokl. Akad. Nauk SSSR, 1960, 134, 856-859. [all data]
Benson and Amano, 1962
Benson, S.W.; Amano, A.,
Thermodynamics of iodine addition to ethylene, propylene, and cyclopropane,
J. Chem. Phys., 1962, 36, 3464-3471. [all data]
Rozhnov and Andreevskii, 1962
Rozhnov, A.M.; Andreevskii, D.N.,
Equilibrium in the system propene, hydrogen bromide, bromopropane,
Dokl. Akad. Nauk SSSR, 1962, 147, 388-391. [all data]
Moore, 1971
Moore, L.O.,
Kinetics and thermodynamic data for the hydrogen fluoride addition to vinyl fluoride,
Can. J. Chem., 1971, 49, 2471-2475. [all data]
Schroeder, Hrusak, et al., 1995
Schroeder, D.; Hrusak, J.; Hertwig, R.H.; Koch, W.; Schwerdtfeger, P.; Schwarz, H.,
Experimental and Theoretical Studies of Gold(I) Complexes Au(L)+ (L=H2O, CO, NH3, C2H4, C3H6, C4H6, C6H6, C6F6),
Organometallics, 1995, 14, 1, 312, https://doi.org/10.1021/om00001a045
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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