Neopentane
- Formula: C5H12
- Molecular weight: 72.1488
- IUPAC Standard InChIKey: CRSOQBOWXPBRES-UHFFFAOYSA-N
- CAS Registry Number: 463-82-1
- 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. - Other names: Propane, 2,2-dimethyl-; tert-Pentane; Tetramethylcarbon; Tetramethylmethane; 1,1,1-Trimethylethane; 2,2-Dimethylpropane; Neo-C5H12; UN 2044; Dimethylpropane
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -40.14 ± 0.15 | kcal/mol | Ccb | Good, 1970 | ALS |
ΔfH°gas | -40.27 ± 0.24 | kcal/mol | Cm | Pilcher and Chadwick, 1967 | ALS |
ΔfH°gas | -39.67 ± 0.25 | kcal/mol | Ccb | Prosen and Rossini, 1945 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -839.88 ± 0.23 | kcal/mol | Cm | Pilcher and Chadwick, 1967 | Corresponding ΔfHºgas = -40.27 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
28.877 ± 0.060 | 298.15 | Hossenlopp I.A., 1981 | GT |
30.970 ± 0.062 | 323.15 | ||
33.081 ± 0.067 | 348.15 | ||
35.148 ± 0.069 | 373.15 | ||
37.156 ± 0.074 | 398.15 | ||
39.082 ± 0.076 | 423.15 | ||
40.980 ± 0.081 | 448.15 | ||
42.770 ± 0.086 | 473.15 | ||
44.555 ± 0.088 | 498.15 | ||
46.219 ± 0.093 | 523.15 |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
19.25 | 200. | Scott D.W., 1974 | Recommended values were obtained from the consistent correlation scheme for alkanes [ Scott D.W., 1974, 2, Scott D.W., 1974]. This approach gives a better agreement with experimental data than the statistical thermodynamics calculation [ Pitzer K.S., 1946].; GT |
26.680 | 273.15 | ||
28.879 ± 0.060 | 298.15 | ||
29.051 | 300. | ||
37.280 | 400. | ||
44.689 | 500. | ||
51.300 | 600. | ||
57.101 | 700. | ||
62.400 | 800. | ||
67.000 | 900. | ||
71.200 | 1000. | ||
74.900 | 1100. | ||
78.200 | 1200. | ||
80.999 | 1300. | ||
84.001 | 1400. | ||
85.999 | 1500. |
Condensed phase thermochemistry data
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -45.49 ± 0.15 | kcal/mol | Ccb | Good, 1970 | ALS |
ΔfH°liquid | -44.98 ± 0.25 | kcal/mol | Ccb | Prosen and Rossini, 1945 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -834.71 ± 0.14 | kcal/mol | Ccb | Good, 1970 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -834.66 ± 0.12 kcal/mol; Corresponding ΔfHºliquid = -45.44 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -835.18 ± 0.24 | kcal/mol | Ccb | Prosen and Rossini, 1945 | Corresponding ΔfHºliquid = -44.97 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 51.819 | cal/mol*K | N/A | Enokida, Shinoda, et al., 1969 | At normal boiling point.; DH |
S°liquid | 52.29 | cal/mol*K | N/A | Aston and Messerly, 1936 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.589 | 259.93 | Enokida, Shinoda, et al., 1969 | T = 4 to 260 K. Value is unsmoothed experimental datum.; DH |
39.171 | 278.92 | Aston and Messerly, 1936 | T = 13 to 283 K. Value is unsmoothed experimental datum.; DH |
Reaction thermochemistry data
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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
MS - José A. Martinho Simões
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
C5H11- + =
By formula: C5H11- + H+ = C5H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 408.9 ± 2.0 | kcal/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrH° | 411. ± 10. | kcal/mol | CIDT | Graul and Squires, 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 400.1 ± 2.1 | kcal/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
C10H22Mg (cr) + (g) +
(l) = 2
(l) + Br2Mg (cr)
By formula: C10H22Mg (cr) + H2 (g) + Br2 (l) = 2C5H12 (l) + Br2Mg (cr)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -160.0 ± 1.6 | kcal/mol | RSC | Akkerman, Schat, et al., 1983 | MS |
Gas phase ion energetics data
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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:
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
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) | ≤10.30 ± 0.08 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.21 ± 0.04 | PE | Jonas, Schweitzer, et al., 1973 | LLK |
10.3 ± 0.1 | PE | Evans, Green, et al., 1972 | LLK |
10.40 | PE | Dewar and Worley, 1969 | RDSH |
10.35 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
10.90 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.9 ± 0.1 | PE | Bieri, Burger, et al., 1977 | Vertical value; LLK |
11.3 | PE | Schmidt and Wilkins, 1972 | Vertical value; LLK |
11.3 | PE | Murrell and Schmidt, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 29.5 ± 0.2 | ? | EI | Olmsted, Street, et al., 1964 | RDSH |
CH3+ | 13.14 | ? | EI | Lampe and Field, 1959 | RDSH |
C2H3+ | 17.95 | ? | EI | Lampe and Field, 1959 | RDSH |
C2H5+ | 13.81 | ? | EI | Lampe and Field, 1959 | RDSH |
C3H3+ | 17.08 | ? | EI | Lampe and Field, 1959 | RDSH |
C3H5+ | 13.13 | ? | EI | Lampe and Field, 1959 | RDSH |
C4H8+ | 10.39 ± 0.02 | CH4 | PI | Steiner, Giese, et al., 1961 | RDSH |
C4H9+ | 10.35 | CH3 | PI | Chesnavich, Su, et al., 1978 | LLK |
C4H9+ | 10.56 | CH3 | EI | Lossing and Semeluk, 1970 | RDSH |
C4H9+ | 10.57 ± 0.02 | CH3 | PI | Steiner, Giese, et al., 1961 | RDSH |
De-protonation reactions
C5H11- + =
By formula: C5H11- + H+ = C5H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 408.9 ± 2.0 | kcal/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrH° | 411. ± 10. | kcal/mol | CIDT | Graul and Squires, 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 400.1 ± 2.1 | kcal/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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.
Good, 1970
Good, W.D.,
The enthalpies of combustion and formation of the isomeric pentanes,
J. Chem. Thermodyn., 1970, 2, 237-244. [all data]
Pilcher and Chadwick, 1967
Pilcher, G.; Chadwick, J.D.M.,
Measurements of heats of combustion by flame calorimetry. Part 4.-n-Pentane, isopentane, neopentane,
Trans. Faraday Soc., 1967, 63, 2357-2361. [all data]
Prosen and Rossini, 1945
Prosen, E.J.; Rossini, F.D.,
Heats of combustion and formation of the paraffin hydrocarbons at 25° C,
J. Res. NBS, 1945, 263-267. [all data]
Hossenlopp I.A., 1981
Hossenlopp I.A.,
Vapor heat capacities and enthalpies of vaporization of five alkane hydrocarbons,
J. Chem. Thermodyn., 1981, 13, 415-421. [all data]
Scott D.W., 1974
Scott D.W.,
Chemical Thermodynamic Properties of Hydrocarbons and Related Substances. Properties of the Alkane Hydrocarbons, C1 through C10 in the Ideal Gas State from 0 to 1500 K. U.S. Bureau of Mines, Bulletin 666, 1974. [all data]
Scott D.W., 1974, 2
Scott D.W.,
Correlation of the chemical thermodynamic properties of alkane hydrocarbons,
J. Chem. Phys., 1974, 60, 3144-3165. [all data]
Pitzer K.S., 1946
Pitzer K.S.,
The entropies and related properties of branched paraffin hydrocarbons,
Chem. Rev., 1946, 39, 435-447. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Enokida, Shinoda, et al., 1969
Enokida, H.; Shinoda, T.; Mashiko, Y.,
Thermodynamic properties of neopentane from 4K to the melting point and comparison with spectroscopic data,
Bull. Chem. Soc. Japan, 1969, 42, 84-91. [all data]
Aston and Messerly, 1936
Aston, J.G.; Messerly, G.H.,
Heat capacities and entropies of organic compounds. II. Thermal and vapor pressure data for tetramethylmethane from 13.22°K to the boiling point. The entropy from its Raman spectrum,
J. Am. Chem. Soc., 1936, 58, 2354-2361. [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]
Graul and Squires, 1990
Graul, S.T.; Squires, R.R.,
Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions,
J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007
. [all data]
Akkerman, Schat, et al., 1983
Akkerman, O.S.; Schat, G.; Evers, E.A.I.M.; Bickelhaupt, F.,
Recl. Trav. Chim. Pays-Bas, 1983, 102, 109. [all data]
Jonas, Schweitzer, et al., 1973
Jonas, A.E.; Schweitzer, G.K.; Grimm, F.A.; Carlson, T.A.,
The photoelectron spectra of the tetrafluoro and tetramethyl compounds of the group IV elements,
J. Electron Spectrosc. Relat. Phenom., 1973, 1, 29. [all data]
Evans, Green, et al., 1972
Evans, S.; Green, J.C.; Joachim, P.J.; Orchard, A.F.; Turner, D.W.; Maier, J.P.,
Electronic structures of the Group IVB tetramethyls by helium-(I) photoelectron spectroscopy,
J. Chem. Soc. Faraday Trans. 2, 1972, 68, 905. [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]
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]
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]
Schmidt and Wilkins, 1972
Schmidt, W.; Wilkins, B.T.,
Das "Equivalent Orbital" (EO)-verfahren zur interpretation von photoelektronen(PE)-spektren: Neopentan,
Angew. Chem., 1972, 84, 168. [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]
Lampe and Field, 1959
Lampe, F.W.; Field, F.H.,
The decomposition of neopentane under electron impact,
J. Am. Chem. Soc., 1959, 81, 3238. [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]
Chesnavich, Su, et al., 1978
Chesnavich, W.J.; Su, T.; Bowers, M.T.,
Reactions of vibrationally excited ions. A theoretical and experimental analysis of the reaction (C4H9+) + NH3 Ü NH4+ + C4H8,
J. Am. Chem. Soc., 1978, 100, 4362. [all data]
Lossing and Semeluk, 1970
Lossing, F.P.; Semeluk, G.P.,
Free radicals by mass spectrometry. XLII.Ionization potentials and ionic heats of formation for C1-C4 alkyl radicals,
Can. J. Chem., 1970, 48, 955. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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