1-Hexene
- Formula: C6H12
- Molecular weight: 84.1595
- IUPAC Standard InChI: InChI=1S/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3
- IUPAC Standard InChIKey: LIKMAJRDDDTEIG-UHFFFAOYSA-N
- CAS Registry Number: 592-41-6
- 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: Hexene-1; 1-n-Hexene; 1-C6H12; Butylethylene; Hexene; Hex-1-ene; UN 2370; Hexylene; Neodene 6 XHP; NSC 74121; Dialene 6
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Gas phase thermochemistry 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -10.2 ± 0.6 | kcal/mol | AVG | N/A | Average of 10 values; Individual data points |
Reaction thermochemistry data
Go To: Top, Gas phase 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
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
+
=
By formula: H2 + C6H12 = C6H14
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -30.0 ± 0.6 | kcal/mol | AVG | N/A | Average of 8 values; Individual data points |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.336 ± 0.037 | kcal/mol | Eqk | Wiberg and Wasserman, 1981 | liquid phase; Trifluoroacetolysis; ALS |
| ΔrH° | -3.27 ± 0.23 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.372 ± 0.037 | kcal/mol | Eqk | Wiberg and Wasserman, 1981 | liquid phase; Trifluoroacetolysis; ALS |
| ΔrH° | -1.57 ± 0.31 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.86 ± 0.04 | kcal/mol | Eqk | Wiberg and Wasserman, 1981 | liquid phase; Trifluoroacetolysis; ALS |
| ΔrH° | -2.75 ± 0.24 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.60 ± 0.04 | kcal/mol | Eqk | Wiberg and Wasserman, 1981 | liquid phase; Trifluoroacetolysis; ALS |
| ΔrH° | -3.14 ± 0.31 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
+
By formula: C6H14O = C6H12 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 8.07 ± 0.08 | kcal/mol | Cm | Wiberg, Wasserman, et al., 1984 | liquid phase; Heat of hydration, see Wiberg and Wasserman, 1981; ALS |
=
+
By formula: C6H14O = C6H12 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 7.68 ± 0.08 | kcal/mol | Cm | Wiberg, Wasserman, et al., 1984 | liquid phase; Heat of hydration, see Wiberg and Wasserman, 1981; ALS |
=
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; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.38 ± 0.29 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.83 ± 0.37 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -6.25 ± 0.27 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -5.26 ± 0.28 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -8.30 ± 0.21 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -3.50 ± 0.18 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -4.58 ± 0.26 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -3.52 ± 0.28 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -5.55 ± 0.34 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -3.80 ± 0.30 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
=
By formula: C6H12 = C6H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -7.18 ± 0.27 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc; ALS |
+
=
By formula: C6H12 + H2O = C6H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -8.25 ± 0.08 | kcal/mol | Cm | Wiberg and Wasserman, 1981 | liquid phase; solvent: Water; Hydration; ALS |
C12H16CrO5 (solution) + (solution) = C11H12CrO5 (solution) +
(solution)
By formula: C12H16CrO5 (solution) + C6H12 (solution) = C11H12CrO5 (solution) + C7H16 (solution)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -12.2 ± 1.2 | kcal/mol | PAC | Yang, Peters, et al., 1986 | solvent: Heptane; MS |
+
=
By formula: C6H12 + C2HF3O2 = C8H13F3O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -12.07 ± 0.03 | kcal/mol | Eqk | Wiberg and Wasserman, 1981 | liquid phase; Trifluoroacetolysis; ALS |
C10H11ClZr (cr) + (l) = C16H23ClZr (cr)
By formula: C10H11ClZr (cr) + C6H12 (l) = C16H23ClZr (cr)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -15.3 ± 0.98 | kcal/mol | RSC | Diogo, Simoni, et al., 1993 | MS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
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
View reactions leading to C6H12+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.44 ± 0.04 | eV | N/A | N/A | L |
| Quantity | Value | Units | Method | Reference | Comment |
| Proton affinity (review) | 192.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 185.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.46 ± 0.05 | EI | Holmes and Lossing, 1991 | LL |
| 9.37 ± 0.02 | PE | Ashmore and Burgess, 1978 | LLK |
| 9.44 | EI | Lossing and Traeger, 1975 | LLK |
| 9.44 | EI | Lossing and Traeger, 1975, 2 | LLK |
| 9.478 ± 0.003 | PE | Masclet, Grosjean, et al., 1973 | LLK |
| 9.31 | PE | Hoshino, Tajima, et al., 1973 | LLK |
| 9.33 | EI | Hoshino, Tajima, et al., 1973 | LLK |
| 9.46 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
| 9.45 ± 0.02 | PI | Steiner, Giese, et al., 1961 | RDSH |
| 9.65 ± 0.01 | PE | Krause, Taylor, et al., 1978 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C5H9+ | 10.02 | CH3 | EI | Lossing and Traeger, 1975, 2 | LLK |
References
Go To: Top, Gas 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.
Wiberg and Wasserman, 1981
Wiberg, K.B.; Wasserman, D.J.,
Enthalpies of hydration of alkenes. 1. The n-hexenes,
J. Am. Chem. Soc., 1981, 103, 6563-6566. [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]
Wiberg, Wasserman, et al., 1984
Wiberg, K.B.; Wasserman, D.J.; Martin, E.,
Enthalpies of hydration of alkenes. 2. The n-heptenes and n-pentenes,
J. Phys. Chem., 1984, 88, 3684-3688. [all data]
Yang, Peters, et al., 1986
Yang, G.K.; Peters, K.S.; Vaida, V.,
Chem. Phys. Lett., 1986, 125, 566. [all data]
Diogo, Simoni, et al., 1993
Diogo, H.P.; Simoni, J.A.; Minas da Piedade, M.E.; Dias, A.R.; Martinho Simões, J.A.,
J. Am. Chem. Soc., 1993, 115, 2764. [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]
Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P.,
Ionization energies of homologous organic compounds and correlation with molecular size,
Org. Mass Spectrom., 1991, 26, 537. [all data]
Ashmore and Burgess, 1978
Ashmore, F.S.; Burgess, A.R.,
Photoelectron spectra of the unbranched C5-C7 alkenes, aldehydes and ketones,
J. Chem. Soc. Faraday Trans. 2, 1978, 74, 734. [all data]
Lossing and Traeger, 1975
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]
Lossing and Traeger, 1975, 2
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]
Hoshino, Tajima, et al., 1973
Hoshino, H.; Tajima, S.; Tsuchiya, T.,
The effect of the temperature on the mass spectra of aliphatic primary alcohols and 1-alkenes. I.,
Bull. Chem. Soc. Jpn., 1973, 46, 3043. [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]
Krause, Taylor, et al., 1978
Krause, D.A.; Taylor, J.W.; Fenske, R.F.,
An analysis of the effects of alkyl substituents on the ionization potentials of n-alkenes,
J. Am. Chem. Soc., 1978, 100, 718. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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