2,4-Hexadiene, (E,E)-
- Formula: C6H10
- Molecular weight: 82.1436
- IUPAC Standard InChIKey: APPOKADJQUIAHP-GGWOSOGESA-N
- CAS Registry Number: 5194-51-4
- 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. - Stereoisomers:
- Other names: (E),(E)-CH3CH=CHCH=CHCH3; trans,trans-2,4-Hexadiene; trans,trans-hexa-2,4-diene
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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 | 10.6 ± 0.4 | kcal/mol | Chyd | Fang and Rogers, 1992 |
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
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 355. | K | N/A | Farchan Laboratories, 1990 | BS |
Tboil | 355.4 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 355.33 | K | N/A | Anonymous, 1963 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 228.3 | K | N/A | Anonymous, 1963 | Uncertainty assigned by TRC = 0.4 K; TRC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.93 | 319. | A | Stephenson and Malanowski, 1987 | Based on data from 304. to 354. K.; AC |
7.93 | 308. | MM | Letcher and Marsicano, 1974 | Based on data from 305. to 323. 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: C6H10 = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.10 | kcal/mol | Eqk | Buechele, Weitz, et al., 1984 | gas phase |
ΔrH° | -0.841 | kcal/mol | Eqk | Petrova-Kuminskaya, Roganov, et al., 1984 | gas phase; At 458 K, see Petrova-Kuminskaya, Baranov, et al., 1983 |
By formula: 2H2 + C6H10 = C6H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -50.5 ± 0.4 | kcal/mol | Chyd | Fang and Rogers, 1992 | liquid phase; solvent: Cyclohexane |
By formula: C6H10 = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -3.059 | kcal/mol | Eqk | Petrova-Kuminskaya, Roganov, et al., 1984 | gas phase; At 458 K, see Petrova-Kuminskaya, Baranov, et al., 1983 |
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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C6H10+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.26 ± 0.05 | EI | Wolkoff, Holmes, et al., 1980 | LLK |
8.22 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
8.09 | PE | Beez, Bieri, et al., 1973 | LLK |
8.19 | PE | Masclet, Mouvier, et al., 1981 | Vertical value; LLK |
8.93 | PE | Sustmann and Schubert, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H7+ | 10.14 ± 0.05 | CH3 | EI | Wolkoff, Holmes, et al., 1980 | LLK |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 114485 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Squalane | 70. | 645. | Safina, Poznyak, et al., 1989 | He, Risorb (0.2-0.3 mm); Column length: 2. m |
Capillary | SE-30 | 130. | 662. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | SE-30 | 80. | 662. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Packed | Squalane | 27. | 645. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 646. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 647. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 648. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 654. | Chupalov and Zenkevich, 1996 | N2, 3. K/min; Column length: 52. m; Column diameter: 0.26 mm; Tstart: 50. C; Tend: 220. C |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Fang and Rogers, 1992
Fang, W.; Rogers, D.W.,
Enthalpy of hydrogenation of the hexadienes and cis- and trans-1,3,5-hexatriene,
J. Org. Chem., 1992, 57, 2294-2297. [all data]
Farchan Laboratories, 1990
Farchan Laboratories,
Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Anonymous, 1963
Anonymous, R.,
, E. I. Du Pont, 1963. [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]
Letcher and Marsicano, 1974
Letcher, T.M.; Marsicano, F.,
Vapour pressures and densities of some unsaturated C6 acyclic and cyclic hydrocarbons between 300 and 320 K,
The Journal of Chemical Thermodynamics, 1974, 6, 5, 509-514, https://doi.org/10.1016/0021-9614(74)90013-5
. [all data]
Buechele, Weitz, et al., 1984
Buechele, J.L.; Weitz, E.; Lewis, F.D.,
Laser-induced infrared multiphoton isomerization reactions of 2,4- and 1,3-hexadienes,
J. Phys. Chem., 1984, 88, 868-876. [all data]
Petrova-Kuminskaya, Roganov, et al., 1984
Petrova-Kuminskaya, S.V.; Roganov, G.N.; Kabo, G.Ya.,
Enthalpies of formation and isomerization of alkadienes,
Probl. Kalorim. Khim. Termodin., Dokl. Vses. Konf., 10th, 1984, 1, 234-236. [all data]
Petrova-Kuminskaya, Baranov, et al., 1983
Petrova-Kuminskaya, S.V.; Baranov, O.M.; Roganov, G.N.; Kabo, G.Ya.,
Equilibrium and thermodynamics of the isomerization of hexadienes,
Neftekhimiya, 1983, 23, 489-494. [all data]
Wolkoff, Holmes, et al., 1980
Wolkoff, P.; Holmes, J.L.; Lossing, F.P.,
On the formation of cyclopentenium cations from all C6H10+ molecular ion structures,
Can. J. Chem., 1980, 58, 251. [all data]
Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P.,
Valence ionization enrgies of hydrocarbons,
Helv. Chim. Acta, 1977, 60, 2213. [all data]
Beez, Bieri, et al., 1973
Beez, M.; Bieri, G.; Bock, H.; Heilbronner, E.,
The ionization potentials of butadiene, hexatriene, andtheir methyl derivatives: evidence for through space interaction between double bond π-orbitals and non-bonded pseudo-π orbitals of methyl groups?,
Helv. Chim. Acta, 1973, 56, 1028. [all data]
Masclet, Mouvier, et al., 1981
Masclet, P.; Mouvier, G.; Bocquet, J.F.,
Effets electroniques et effets steriques dus a la substitution alcoyle dans les dienes conjugues,
J. Chim. Phys., 1981, 78, 99. [all data]
Sustmann and Schubert, 1972
Sustmann, R.; Schubert, R.,
Photoelektronenspektroskopische bestimmung von substituenten-effekten. I. Subtituierte butadiene,
Tetrahedron Lett., 1972, 27, 2739. [all data]
Safina, Poznyak, et al., 1989
Safina, L.R.; Poznyak, T.I.; Lisitsyn, D.M.; Kiseleva, E.V.; Kovalev, G.I.,
Selective gas-chromatographic determination of trace unsaturated and aromatic-hydrocarbons in complex-mixtures,
J. Appl. Chem. USSR (Engl. Transl.), 1989, 44, 5, 749-754. [all data]
Bredael, 1982
Bredael, P.,
Retention indices of hydrocarbons on SE-30,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610
. [all data]
Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203
. [all data]
Chupalov and Zenkevich, 1996
Chupalov, A.A.; Zenkevich, I.G.,
Chromatographic Characterization of Structural Transformations of Organic Compounds in Diels-Alder Reaction. Aliphatic Dienes and Dienophyls,
Zh. Org. Khim., 1996, 32, 6, 675-684. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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