3-Hexene, (Z)-

Formula: C₆H₁₂
Molecular weight: 84.1595
IUPAC Standard InChI: InChI=1S/C6H12/c1-3-5-6-4-2/h5-6H,3-4H2,1-2H3/b6-5-
IUPAC Standard InChIKey: ZQDPJFUHLCOCRG-WAYWQWQTSA-N
CAS Registry Number: 7642-09-3
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Stereoisomers:
- 3-Hexene, (E)-
- 3-Hexene
Other names: (Z)-3-Hexene; cis-3-Hexene; (Z)-3-C6H12
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Gas phase thermochemistry data

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Data compiled by: Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-11.0 ± 0.2	kcal/mol	Chyd	Rogers, Crooks, et al., 1987	Value computed using Δ_fH_liquid° from Rogers, Crooks, et al., 1987 and Δ_vapH° value of 7.46 kcal/mol from Steele and Chirico, 1993.
Δ_fH°_gas	-11.5 ± 0.33	kcal/mol	Chyd	Rogers and Crooks, 1983	Value computed using Δ_fH_liquid° from Rogers and Crooks, 1983 and Δ_vapH° value of 7.46 kcal/mol from Steele and Chirico, 1993.
Δ_fH°_gas	-11.3	kcal/mol	N/A	Wiberg and Wasserman, 1981	Value computed using Δ_fH_liquid° value of -78.07±0.84 kj/mol from Wiberg and Wasserman, 1981 and Δ_vapH° value of 30.7 kj/mol from alkenes correlation.
Δ_fH°_gas	-11.2 ± 0.2	kcal/mol	Eqk	Wiberg and Wasserman, 1981	Value computed using Δ_fH_liquid° from Wiberg and Wasserman, 1981 and Δ_vapH° value of 7.46 kcal/mol from Steele and Chirico, 1993.
Δ_fH°_gas	-11.5 ± 0.33	kcal/mol	Chyd	Rogers, Papadimetriou, et al., 1975	Value computed using Δ_fH_liquid° from Rogers, Papadimetriou, et al., 1975 and Δ_vapH° value of 7.46 kcal/mol from Steele and Chirico, 1993.

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

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-18.4 ± 0.2	kcal/mol	Chyd	Rogers, Crooks, et al., 1987	DRB
Δ_fH°_liquid	-19.0 ± 0.33	kcal/mol	Chyd	Rogers and Crooks, 1983	DRB
Δ_fH°_liquid	-18.66 ± 0.20	kcal/mol	Eqk	Wiberg and Wasserman, 1981	ALS
Δ_fH°_liquid	-18.9 ± 0.33	kcal/mol	Chyd	Rogers, Papadimetriou, et al., 1975	DRB

Gas phase ion energetics data

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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)

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.954 ± 0.005	PE	Masclet, Grosjean, et al., 1973	LLK
9.15 ± 0.01	PE	Krause, Taylor, et al., 1978	Vertical value; LLK

References

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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]

Steele and Chirico, 1993
Steele, W.V.; Chirico, R.D., Thermodynamic properties of alkenes (mono-olefins larger than C₄), J. Phys. Chem. Ref. Data, 1993, 22, 377-430. [all data]

Rogers and Crooks, 1983
Rogers, D.W.; Crooks, E.L., Enthalpies of hydrogenation of the isomers of n-hexene, J. Chem. Thermodyn., 1983, 15, 1087-1092. [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]

Rogers, Papadimetriou, et al., 1975
Rogers, D.W.; Papadimetriou, P.M.; Siddiqui, N.A., An improved hydrogen microcalorimeter for use with large molecules, Mikrochim. Acta, 1975, 2, 389-400. [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]

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:

Δ_fH°_gas Enthalpy of formation of gas at standard conditions

Δ_fH°_liquid Enthalpy of formation of liquid at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions