trans-1,2-di-tert-butylethylene
- Formula: C10H20
- Molecular weight: 140.2658
- IUPAC Standard InChI: InChI=1S/C10H20/c1-9(2,3)7-8-10(4,5)6/h7-8H,1-6H3/b8-7+
- IUPAC Standard InChIKey: UYWLQEPMPVDASH-BQYQJAHWSA-N
- CAS Registry Number: 692-48-8
- 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: 3-Hexene, 2,2,5,5-tetramethyl-, (E)-; (E)-2,2,5,5-tetramethylhex-3-ene; (E)-2,2,5,5-Tetramethyl-3-hexene
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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 | -167. | kJ/mol | Chyd | Doering, Roth, et al., 1989 | |
| ΔfH°gas | -165.5 ± 2.7 | kJ/mol | Cm | Fuchs and Peacock, 1979 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°liquid | -6585.9 ± 2.5 | kJ/mol | Ccb | Rockenfeller and Rossini, 1961 | Derived from the ratio of Heat of combustion; Corresponding ΔfHºliquid = -207.5 kJ/mol (simple calculation by NIST; no Washburn corrections) |
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:
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 | 398.3 | K | N/A | Turner, Nettleton, et al., 1958 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Tboil | 398.3 | K | N/A | Bader, Buckley, et al., 1957 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tboil | 398.3 | K | N/A | Newman, 1956 | Uncertainty assigned by TRC = 4. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 268.4 | K | N/A | Turner, Nettleton, et al., 1958 | Uncertainty assigned by TRC = 0.4 K; TRC |
| Tfus | 268.4 | K | N/A | Bader, Buckley, et al., 1957 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tfus | 268. | K | N/A | Yohe, Dunbar, et al., 1956 | Uncertainty assigned by TRC = 4. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 42.0 ± 0.3 | kJ/mol | C | Fuchs and Peacock, 1979 | ALS |
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: H2 + C10H20 = C10H22
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -118. | kJ/mol | Chyd | Doering, Roth, et al., 1989 | liquid phase |
| ΔrH° | -113. | kJ/mol | Chyd | Turner, Nettleton, et al., 1958, 2 | liquid phase; solvent: Acetic acid |
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.741 ± 0.008 | PE | Masclet, Grosjean, et al., 1973 | LLK |
| 8.73 ± 0.01 | PI | Demeo and El-Sayed, 1970 | RDSH |
| 8.89 | PE | Robin, Taylor, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C4H9+ | 11.23 ± 0.05 | ? | EI | Natalis and Franklin, 1966 | RDSH |
| C5H9+ | 12.06 ± 0.05 | ? | EI | Natalis and Franklin, 1966 | RDSH |
| C5H10+ | 9.60 ± 0.05 | ? | EI | Natalis and Franklin, 1966 | RDSH |
| C6H10+ | 8.76 ± 0.08 | C4H10 | EI | Natalis and Franklin, 1966 | RDSH |
| C6H11+ | 10.68 ± 0.04 | ? | EI | Natalis and Franklin, 1966 | RDSH |
| C6H12+ | 9.15 ± 0.06 | C4H8 | EI | Natalis and Franklin, 1966 | RDSH |
| C7H13+ | 10.04 ± 0.05 | C3H7 | EI | Natalis and Franklin, 1966 | RDSH |
| C9H17+ | 10.70 ± 0.06 | CH3 | EI | Natalis and Franklin, 1966 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
Doering, Roth, et al., 1989
Doering, W.E.; Roth, W.R.; Bauer, F.; Breuckmann, R.; Ebbrecht, T.; Herbold, M.; Schmidt, R.; Lennartz, H-W.; Lenoir, D.; Boese, R.,
Rotational barriers of strained olefines,
Chem. Ber., 1989, 122, 1263-1266. [all data]
Fuchs and Peacock, 1979
Fuchs, R.; Peacock, L.A.,
Heats of vaporization and gaseous heats of formation of some five- and six-membered ring alkenes,
Can. J. Chem., 1979, 57, 2302-2304. [all data]
Rockenfeller and Rossini, 1961
Rockenfeller, J.D.; Rossini, F.D.,
Heats of combustion, isomerization, and formation of selected C7, C8, and C10 monoolefin hydrocarbons,
J. Phys. Chem., 1961, 65, 267-272. [all data]
Turner, Nettleton, et al., 1958
Turner, R.B.; Nettleton, D.E.; Perelman, M.,
Heats of Hydrogenation VI. Heats of Hydr. of SOm Substituted Ethylenes,
J. Am. Chem. Soc., 1958, 80, 1430. [all data]
Bader, Buckley, et al., 1957
Bader, A.R.; Buckley, R.P.; Leavitt, F.; Szwarc, M.,
J. Am. Chem. Soc., 1957, 79, 5621. [all data]
Newman, 1956
Newman, M.,
Private Communication, Ohio State Univ., 1956. [all data]
Yohe, Dunbar, et al., 1956
Yohe, G.R.; Dunbar, J.E.; Pedrotti, R.L.; Scheidt, F.M.; Lee, F.G.H.; Smith, E.C.,
J. Org. Chem., 1956, 21, 1289. [all data]
Turner, Nettleton, et al., 1958, 2
Turner, R.B.; Nettleton, J.E.; Perelman,
Heats of Hydrogenation. VI. Heats of hydrogenation of some substituted ethylenes,
J. Am. Chem. Soc., 1958, 80, 1430-1433. [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]
Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A.,
Ionization potential and structure of olefins,
J. Chem. Phys., 1970, 52, 2622. [all data]
Robin, Taylor, et al., 1973
Robin, M.B.; Taylor, G.N.; Kuebler, N.A.; Bach, R.D.,
Planarity of the carbon skeleton in various alkylated olefins,
J. Org. Chem., 1973, 38, 1049. [all data]
Natalis and Franklin, 1966
Natalis, P.; Franklin, J.L.,
Etude du comportement d'isomeres geometriques sous l'impact electronique. VI. Les cis- et trans-1,2-di-terbutyl-ethylenes,
Bull. Soc. Chim. Belges, 1966, 75, 328. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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 ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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