2,4-Hexadiene, 2,5-dimethyl-
- Formula: C8H14
- Molecular weight: 110.1968
- IUPAC Standard InChIKey: DZPCYXCBXGQBRN-UHFFFAOYSA-N
- CAS Registry Number: 764-13-6
- 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: Biisobutenyl; Biisocrotyl; Diisocrotyl; 2,5-Dimethyl-2,4-hexadiene; (CH3)2C=CHCH=C(CH3)2; 2,5-Dimethylhexa-2,4-diene; NSC 10812
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -19.20 ± 0.84 | kJ/mol | Ccr | Steele, Chirico, et al., 1990 |
Condensed 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 as indicated in comments:
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 |
---|---|---|---|---|---|
ΔfH°liquid | -63.12 ± 0.84 | kJ/mol | Ccr | Steele, Chirico, et al., 1990 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5085.77 ± 0.70 | kJ/mol | Ccr | Steele, Chirico, et al., 1990 | Corresponding ΔfHºliquid = -63.12 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
459.0 | 298.15 | Steele, Chirico, et al., 1990 | Authors give Cp/R = 55.2. This value appears too large by a factor of two. Actual Cp should be around 229.5 J/mol*K.; DH |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 407. ± 2. | K | AVG | N/A | Average of 13 out of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 287.1 ± 0.6 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 43.92 ± 0.05 | kJ/mol | V | Steele, Chirico, et al., 1990 | ALS |
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:
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
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.67 | PE | Masclet, Mouvier, et al., 1981 | LLK |
7.65 | PE | Beez, Bieri, et al., 1973 | LLK |
7.91 ± 0.04 | EI | Franklin and Mogenis, 1967 | RDSH |
7.67 | PE | Werstiuk, Clark, et al., 1990 | Vertical value; LL |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 26.5 ± 0.1 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
C3H5+ | 14.27 ± 0.03 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
C3H7+ | 12.23 ± 0.06 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
C4H5+ | 14.60 ± 0.04 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
C4H7+ | 13.03 ± 0.02 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
C5H7+ | 12.88 ± 0.03 | C2H4+CH3 | EI | Franklin and Mogenis, 1967 | RDSH |
C6H5+ | 16.1 ± 0.1 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
C6H7+ | 14.42 ± 0.05 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
C6H9+ | 11.7 ± 0.1 | ? | EI | Franklin and Mogenis, 1967 | RDSH |
C7H11+ | 10.80 ± 0.03 | CH3 | EI | Franklin and Mogenis, 1967 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K.,
Determination of ideal-gas enthalpies of formation for key compounds,
Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1990, 138-154. [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]
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]
Franklin and Mogenis, 1967
Franklin, J.L.; Mogenis, A.,
An electron impact study of ions from several dienes,
J. Phys. Chem., 1967, 71, 2820. [all data]
Werstiuk, Clark, et al., 1990
Werstiuk, N.H.; Clark, K.B.; Leigh, W.J.,
Conformational analysis and structure elucidation of 2,3-dimethyl and 2,4-dimethyl-2,4-hexadienes by AM1 and He(I) ultraviolet photoelectron spectroscopy,
Can. J. Chem., 1990, 68, 2078. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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