1-Pentene, 2-methyl-
- Formula: C6H12
- Molecular weight: 84.1595
- IUPAC Standard InChIKey: WWUVJRULCWHUSA-UHFFFAOYSA-N
- CAS Registry Number: 763-29-1
- 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: 2-Methyl-1-pentene; 4-Methyl-4-pentene; C2H5CH2C(CH3)=CH2; 2-Methylpentene; 2-Methyl-pentene-1; 2-methylpent-1-ene
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Phase change data
Go To: Top, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 335. ± 1. | K | AVG | N/A | Average of 16 out of 17 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.29 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 7.29 | kcal/mol | V | Camin and Rossini, 1956 | ALS |
ΔvapH° | 7.29 | kcal/mol | N/A | Camin and Rossini, 1956, 2 | Based on data from 300. to 335. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.55 | 287. | A | Stephenson and Malanowski, 1987 | Based on data from 272. to 341. K.; AC |
Reaction thermochemistry data
Go To: Top, Phase change 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 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: H2 + C6H12 = C6H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -27.80 ± 0.10 | kcal/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
ΔrH° | -27.63 ± 0.52 | kcal/mol | Chyd | Molnar, Rachford, et al., 1984 | liquid phase; solvent: Dioxane |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.13 ± 0.15 | kcal/mol | Eqk | Yursha and Kabo, 1976 | liquid phase; At 394.5K |
ΔrH° | 1.45 ± 0.21 | kcal/mol | Eqk | Radyuk, Kabo, et al., 1972 | gas phase; At 503 K |
By formula: C6H12 + HCl = C6H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -15.46 ± 0.34 | kcal/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.20 ± 0.22 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc |
+
= C21H27ClO
By formula: C15H15ClO + C6H12 = C21H27ClO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -20.0 ± 1.4 | kcal/mol | Cm | Schade, Mayr, et al., 1988 | liquid phase; solvent: Methylene chloride |
+
= C20H25ClO
By formula: C14H13ClO + C6H12 = C20H25ClO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -20.2 ± 1.5 | kcal/mol | Cm | Schade, Mayr, et al., 1988 | liquid phase; solvent: Methylene chloride |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.38 ± 0.04 | kcal/mol | Eqk | Yursha and Kabo, 1976 | liquid phase; At 394.5K |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.47 ± 0.06 | kcal/mol | Eqk | Yursha and Kabo, 1976 | liquid phase; At 394.5K |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.65 ± 0.10 | kcal/mol | Eqk | Yursha and Kabo, 1976 | liquid phase; At 394.5K |
Gas phase ion energetics data
Go To: Top, Phase change data, 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:
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) | 9.08 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.04 | EI | Lossing and Traeger, 1975 | LLK |
9.076 ± 0.005 | PE | Masclet, Grosjean, et al., 1973 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H9+ | 9.04 | CH3 | EI | Lossing and Traeger, 1975, 2 | LLK |
C5H9+ | 10.36 | CH3 | EI | Lossing and Traeger, 1975 | LLK |
References
Go To: Top, 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.
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [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]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [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]
Molnar, Rachford, et al., 1984
Molnar, A.; Rachford, R.; Smith, G.V.; Liu, R.,
Heats of hydrogenation by a simple and rapid flow calorimetric method,
Appl. Catal., 1984, 9, 219-223. [all data]
Yursha and Kabo, 1976
Yursha, I.A.; Kabo, G.Ya.,
Equilibrium isomerisation and thermodynamic properties of 2-methylpentenes,
Russ. J. Phys. Chem. (Engl. Transl.), 1976, 50, 330, In original 558. [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]
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]
Schade, Mayr, et al., 1988
Schade, C.; Mayr, H.; Arnett, E.M.,
Thermochemical study of the addition of carbenium ions to alkenes,
J. Am. Chem. Soc., 1988, 110, 567-571. [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, 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 ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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