Pentane, 3-methylene-
- Formula: C6H12
- Molecular weight: 84.1595
- IUPAC Standard InChIKey: RYKZRKKEYSRDNF-UHFFFAOYSA-N
- CAS Registry Number: 760-21-4
- 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: 1-Butene, 2-ethyl-; 2-Ethyl-1-butene; 3-Methylenepentane; (C2H5)2C=CH2; 1,1-Diethylethene; 2-ethylbut-1-ene
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -56.07 ± 0.88 | kJ/mol | Ccb | Wiberg and Hao, 1991 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -87.2 ± 0.8 | kJ/mol | Ccb | Wiberg and Hao, 1991 |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 339. ± 2. | K | AVG | N/A | Average of 13 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 141.13 | K | N/A | Derfer, Greenlee, et al., 1949 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 141.17 | K | N/A | Boord, Greenlee, et al., 1946 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 31.0 | kJ/mol | V | Camin and Rossini, 1956 | ALS |
ΔvapH° | 31.0 | kJ/mol | N/A | Camin and Rossini, 1956, 2 | Based on data from 289. to 338. K.; AC |
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 by: 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
By formula: C6H12 + HCl = C6H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -58.9 ± 2.0 | kJ/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -14.7 ± 1.2 | kJ/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc |
By formula: H2 + C6H12 = C6H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -115.8 ± 0.36 | kJ/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 5.5 ± 2.1 | kJ/mol | Eqk | Radyuk, Kabo, et al., 1972 | gas phase; At 476 K |
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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C6H12+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.06 ± 0.02 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.01 | EI | Lossing and Traeger, 1975 | LLK |
9.061 ± 0.005 | PE | Masclet, Grosjean, et al., 1973 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H9+ | 9.01 | CH3 | EI | Lossing and Traeger, 1975, 2 | LLK |
C5H9+ | 10.39 | CH3 | EI | Lossing and Traeger, 1975 | LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S.,
Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols,
J. Org. Chem., 1991, 56, 5108-5110. [all data]
Derfer, Greenlee, et al., 1949
Derfer, J.M.; Greenlee, K.W.; Boord, C.E.,
A New Synthesis of Monoalkylcyclobutanes: Reduction of Neopentyl Type Tribromides,
J. Am. Chem. Soc., 1949, 71, 175. [all data]
Boord, Greenlee, et al., 1946
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L.,
The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Weight, Am. Pet. Inst. Res. Proj. 45, Eighth Annu. Rep., Ohio State Univ., June 30, 1946. [all data]
Camin and Rossini, 1956
Camin, D.L.; Rossini, F.D.,
Physical properties of the 17 isomeric hexenes of the API research series,
J. Phys. Chem., 1956, 60, 1446. [all data]
Camin and Rossini, 1956, 2
Camin, David L.; Rossini, Frederick D.,
Physical Properties of the 17 Isomeric Hexenes.of the API Research Series,
J. Phys. Chem., 1956, 60, 10, 1446-1451, https://doi.org/10.1021/j150544a029
. [all data]
Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J.,
Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions,
J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]
Bartolo and Rossini, 1960
Bartolo, H.F.; Rossini, F.D.,
Heats of isomerization of the seventeen isomeric hexenes,
J. Phys. Chem., 1960, 64, 1685-1689. [all data]
Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K.,
Enthalpies of hydrogenation of the hexenes,
J. Chem. Thermodyn., 1987, 19, 1209-1215. [all data]
Radyuk, Kabo, et al., 1972
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N.,
Equilibrium and thermodynamics of the isomerization of hexene isomers,
Neftekhimiya, 1972, 12, 679-686. [all data]
Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C.,
Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations,
J. Am. Chem. Soc., 1975, 97, 1579. [all data]
Masclet, Grosjean, et al., 1973
Masclet, P.; Grosjean, D.; Mouvier, G.,
Alkene ionization potentials. Part I. Quantitative determination of alkyl group structural effects,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 225. [all data]
Lossing and Traeger, 1975, 2
Lossing, F.P.; Traeger, J.C.,
Free radicals by mass spectrometry XLVI. Heats of formation of C5H7 and C5H9 radicals and cations.,
J. Am. Chem. Soc., 1975, 19, 9. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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