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
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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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Condensed phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
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
Δ_fH°_liquid	-73. ± 3.	kJ/mol	AVG	N/A	Average of 9 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	295.18	J/mol*K	N/A	McCullough, Finke, et al., 1957	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
182.77	298.56	Kalinowska and Woycicki, 1985	T = 180 to 300 K. Value is unsmoothed experimental datum.; DH
183.30	298.15	McCullough, Finke, et al., 1957	T = 11 to 360 K.; DH

Reaction thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

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Individual Reactions

+ 1-Hexene =

By formula: H₂ + C₆H₁₂ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-125. ± 3.	kJ/mol	AVG	N/A	Average of 8 values; Individual data points

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-9.77 ± 0.15	kJ/mol	Eqk	Wiberg and Wasserman, 1981	liquid phase; Trifluoroacetolysis; ALS
Δ_rH°	-13.7 ± 0.96	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-5.74 ± 0.15	kJ/mol	Eqk	Wiberg and Wasserman, 1981	liquid phase; Trifluoroacetolysis; ALS
Δ_rH°	-6.6 ± 1.3	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-7.8 ± 0.2	kJ/mol	Eqk	Wiberg and Wasserman, 1981	liquid phase; Trifluoroacetolysis; ALS
Δ_rH°	-11.5 ± 1.0	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-10.9 ± 0.2	kJ/mol	Eqk	Wiberg and Wasserman, 1981	liquid phase; Trifluoroacetolysis; ALS
Δ_rH°	-13.1 ± 1.3	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

= 1-Hexene +

By formula: C₆H₁₄O = C₆H₁₂ + H₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	33.8 ± 0.3	kJ/mol	Cm	Wiberg, Wasserman, et al., 1984	liquid phase; Heat of hydration, see Wiberg and Wasserman, 1981; ALS

= 1-Hexene +

By formula: C₆H₁₄O = C₆H₁₂ + H₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	32.1 ± 0.3	kJ/mol	Cm	Wiberg, Wasserman, et al., 1984	liquid phase; Heat of hydration, see Wiberg and Wasserman, 1981; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-17.6 ± 0.92	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-5.8 ± 1.2	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-7.7 ± 1.5	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-26.2 ± 1.1	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-22.0 ± 1.2	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-34.7 ± 0.88	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-14.6 ± 0.75	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-19.2 ± 1.1	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-14.7 ± 1.2	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-23.2 ± 1.4	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-15.9 ± 1.3	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene =

By formula: C₆H₁₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-30.0 ± 1.1	kJ/mol	Ciso	Bartolo and Rossini, 1960	liquid phase; Calculated from ΔHc; ALS

1-Hexene + =

By formula: C₆H₁₂ + H₂O = C₆H₁₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-34.5 ± 0.3	kJ/mol	Cm	Wiberg and Wasserman, 1981	liquid phase; solvent: Water; Hydration; ALS

C₁₂H₁₆CrO₅ (solution) + 1-Hexene (solution) = C₁₁H₁₂CrO₅ (solution) + (solution)

By formula: C₁₂H₁₆CrO₅ (solution) + C₆H₁₂ (solution) = C₁₁H₁₂CrO₅ (solution) + C₇H₁₆ (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-51.0 ± 5.0	kJ/mol	PAC	Yang, Peters, et al., 1986	solvent: Heptane; MS

1-Hexene + =

By formula: C₆H₁₂ + C₂HF₃O₂ = C₈H₁₃F₃O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-50.5 ± 0.1	kJ/mol	Eqk	Wiberg and Wasserman, 1981	liquid phase; Trifluoroacetolysis; ALS

C₁₀H₁₁ClZr (cr) + 1-Hexene (l) = C₁₆H₂₃ClZr (cr)

By formula: C₁₀H₁₁ClZr (cr) + C₆H₁₂ (l) = C₁₆H₂₃ClZr (cr)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-64.0 ± 4.1	kJ/mol	RSC	Diogo, Simoni, et al., 1993	MS

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes

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)	805.2	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	776.3	kJ/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, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

McCullough, Finke, et al., 1957
McCullough, J.P.; Finke, H.L.; Gross, M.E.; Messerly, J.F.; Waddington, G., Low temperature calorimetric studies of seven 1-olefins: effect of orientational disorder in the solid state, J. Phys. Chem., 1957, 61, 289-301. [all data]

Kalinowska and Woycicki, 1985
Kalinowska, B.; Woycicki, W., Heat capacities and excess heat capacities of (an alcohol + an unsaturated hydrocarbon). 1. (Propan-1-ol + n-hex-1-ene), J. Chem. Thermodynam., 1985, 17, 829-834. [all data]

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

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Symbols used in this document:

AE	Appearance energy
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
S°_liquid	Entropy of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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