Isobutane
- Formula: C4H10
- Molecular weight: 58.1222
- IUPAC Standard InChIKey: NNPPMTNAJDCUHE-UHFFFAOYSA-N
- CAS Registry Number: 75-28-5
- 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: Propane, 2-methyl-; Trimethylmethane; 1,1-Dimethylethane; 2-Methylpropane; iso-C4H10; i-Butane; UN 1969; R 600a; tert-Butane; A 31; Methylpropane; A 31 (hydrocarbon)
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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
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
C4H9- + =
By formula: C4H9- + H+ = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1728. ± 8.4 | kJ/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrH° | 1735. ± 20. | kJ/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1692. ± 8.8 | kJ/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrG° | 1699. ± 21. | kJ/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
C4H9- + =
By formula: C4H9- + H+ = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1728. ± 8.4 | kJ/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrH° | 1732. ± 8.4 | kJ/mol | Bran | DePuy, Bierbaum, et al., 1984 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1697. ± 8.8 | kJ/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -117.8 ± 0.42 | kJ/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1935 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -118.78 ± 0.75 kJ/mol; At 355 °K; ALS |
By formula: C4H10 = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -9.699 | kJ/mol | Eqk | Pines, Kvetinskas, et al., 1945 | gas phase; Heat of isomerization; ALS |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 10.68 ± 0.11 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 677.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 671.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.57 | EST | Luo and Pacey, 1992 | LL |
10.74 ± 0.05 | EI | Flesch and Svec, 1973 | LLK |
10.69 | PI | Dewar and Worley, 1969 | RDSH |
10.79 | PI | Turner and Al-Joboury, 1964 | RDSH |
10.78 | PI | Al-Joboury and Turner, 1964 | RDSH |
10.57 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
~10.5 | PI | Steiner, Giese, et al., 1961 | RDSH |
11.13 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
11.0 ± 0.1 | PE | Bieri, Burger, et al., 1977 | Vertical value; LLK |
11.4 | PE | Murrell and Schmidt, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 29.4 ± 0.2 | ? | EI | Olmsted, Street, et al., 1964 | RDSH |
C2H5+ | 13.80 | C2H5 | EI | Omura, 1961 | RDSH |
C3H5+ | 14.55 | ? | EI | Omura, 1961 | RDSH |
C3H6+ | 10.89 ± 0.02 | CH4 | PI | Mead, Donchi, et al., 1980 | LLK |
C3H6+ | 10.91 | CH4 | EI | Wolkoff and Holmes, 1978 | LLK |
C3H6+ | 10.93 ± 0.03 | CH4 | PI | Steiner, Giese, et al., 1961 | RDSH |
C3H7+ | 11.16 ± 0.02 | CH3 | PI | Mead, Donchi, et al., 1980 | LLK |
C3H7+ | 11.16 ± 0.05 | CH3 | EI | Williams and Hamill, 1968 | RDSH |
C3H7+ | 11.23 ± 0.03 | CH3 | PI | Steiner, Giese, et al., 1961 | RDSH |
C4H9+ | 10.68 ± 0.02 | H | PI | Mead, Donchi, et al., 1980 | LLK |
C4H9+ | 10.68 ± 0.03 | H | PI | McLoughlin and Traeger, 1979 | LLK |
C4H9+ | 11.6 | H | EI | Omura, 1961 | RDSH |
De-protonation reactions
C4H9- + =
By formula: C4H9- + H+ = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1728. ± 8.4 | kJ/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrH° | 1735. ± 20. | kJ/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1692. ± 8.8 | kJ/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrG° | 1699. ± 21. | kJ/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
C4H9- + =
By formula: C4H9- + H+ = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1728. ± 8.4 | kJ/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrH° | 1732. ± 8.4 | kJ/mol | Bran | DePuy, Bierbaum, et al., 1984 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1697. ± 8.8 | kJ/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; 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.
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]
Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M.,
Stabilization of Cycloalkyl Carbanions in the Gas Phase,
Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608
. [all data]
DePuy, Bierbaum, et al., 1984
DePuy, C.H.; Bierbaum, V.M.; Damrauer, R.,
Relative Gas-Phase Acidities of the Alkanes,
J. Am. Chem. Soc., 1984, 106, 4051. [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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Pines, Kvetinskas, et al., 1945
Pines, H.; Kvetinskas, B.; Kassel, L.S.; Ipatieff, V.N.,
Determination of equilibrium constants for butanes and pentanes,
J. Am. Chem. Soc., 1945, 67, 631-637. [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]
Luo and Pacey, 1992
Luo, Y.-R.; Pacey, P.D.,
Effects of alkyl substitution on ionization energies of alkanes and haloalkanes and on heats of formation of their molecular cations. Part 2. Alkanes and chloro-, bromo- and iodoalkanes,
Int. J. Mass Spectrom. Ion Processes, 1992, 112, 63. [all data]
Flesch and Svec, 1973
Flesch, G.D.; Svec, H.J.,
Fragmentation reactions in the mass spectrometer for C2-C5 alkanes,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 1187. [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]
Turner and Al-Joboury, 1964
Turner, D.W.; Al-Joboury, M.I.,
Molecular photoelectron spectroscopy,
Bull. Soc. Chim. Belges, 1964, 73, 428. [all data]
Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W.,
Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials,
J. Chem. Soc., 1964, 4434. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Steiner, Giese, et al., 1961
Steiner, B.; Giese, C.F.; Inghram, M.G.,
Photoionization of alkanes. Dissociation of excited molecular ions,
J. Chem. Phys., 1961, 34, 189. [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]
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]
Murrell and Schmidt, 1972
Murrell, J.N.; Schmidt, W.,
Photoelectron spectroscopic correlation of the molecular orbitals of methane, ethane, propane, isobutane and neopentane,
J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1709. [all data]
Olmsted, Street, et al., 1964
Olmsted, J., III; Street, K., Jr.; Newton, A.S.,
Excess-kinetic-energy ions in organic mass spectra,
J. Chem. Phys., 1964, 40, 2114. [all data]
Omura, 1961
Omura, I.,
Mass spectra at low ionizing voltage and bond dissociation energies of molecular ions from hydrocarbons,
Bull. Chem. Soc. Japan, 1961, 34, 1227. [all data]
Mead, Donchi, et al., 1980
Mead, P.T.; Donchi, K.F.; Traeger, J.C.; Christie, J.R.; Derrick, P.J.,
Secondary hydrogen isotope effect in the unimolecular decomposition of 2-methylpropane radical cations,
J. Am. Chem. Soc., 1980, 102, 3364. [all data]
Wolkoff and Holmes, 1978
Wolkoff, P.; Holmes, J.L.,
Fragmentations of alkane molecular ions,
J. Am. Chem. Soc., 1978, 100, 7346. [all data]
Williams and Hamill, 1968
Williams, J.M.; Hamill, W.H.,
Ionization potentials of molecules and free radicals and appearance potentials by electron impact in the mass spectrometer,
J. Chem. Phys., 1968, 49, 4467. [all data]
McLoughlin and Traeger, 1979
McLoughlin, R.G.; Traeger, J.C.,
Heat of formation for tert-butyl cation in the gas phase,
J. Am. Chem. Soc., 1979, 101, 5791. [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 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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