2-Butene, 2,3-dimethyl-
- Formula: C6H12
- Molecular weight: 84.1595
- IUPAC Standard InChIKey: WGLLSSPDPJPLOR-UHFFFAOYSA-N
- CAS Registry Number: 563-79-1
- 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: Tetramethylethylene; 1,1,2,2-Tetramethylethylene; 2,3-Dimethyl-2-butene; 2,3-Dimethylbut-2-ene; 2,3-Dimethylbutene-2; (CH3)2C=C(CH3)2; Tetramethylethene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -16.80 ± 0.36 | kcal/mol | Eqk | Wiberg and Hao, 1991 | Heat of hydration; ALS |
ΔfH°gas | -16.35 ± 0.35 | kcal/mol | Eqk | Rodgers and Wu, 1971 | Heat of isomerization; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
32.340 ± 0.065 | 334.20 | Scott D.W., 1955 | GT |
33.939 ± 0.067 | 355.25 | ||
36.960 ± 0.074 | 393.20 | ||
40.069 ± 0.081 | 433.20 | ||
43.100 ± 0.086 | 473.20 |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
27.710 | 273.15 | Scott D.W., 1955 | Recommended results of statistical thermodynamics calculation are in good agreement with experimental data.; GT |
29.541 | 298.15 | ||
29.680 | 300. | ||
37.481 | 400. | ||
45.041 | 500. | ||
51.781 | 600. | ||
57.670 | 700. | ||
62.780 | 800. | ||
67.249 | 900. | ||
71.140 | 1000. | ||
74.551 | 1100. | ||
77.510 | 1200. | ||
80.079 | 1300. | ||
82.330 | 1400. | ||
84.309 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 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 | -24.60 ± 0.35 | kcal/mol | Eqk | Wiberg and Hao, 1991 | Heat of hydration; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 64.579 | cal/mol*K | N/A | Scott, Finke, et al., 1955 | DH |
S°liquid | 65.11 | cal/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 58.45 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.750 | 298.15 | Scott, Finke, et al., 1955 | T = 10 to 320 K.; DH |
42.000 | 295.5 | Parks, Todd, et al., 1936 | T = 83 to 296 K. Value is unsmoothed experimental datum.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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
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 + C6H12 = C6H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -25.98 ± 0.11 | kcal/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
ΔrH° | -26.39 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -26.63 ± 0.10 kcal/mol; At 355 K |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.82 ± 0.12 | kcal/mol | Eqk | Radyuk, Kabo, et al., 1972 | gas phase; At 562 K |
ΔrH° | 1.7 ± 0.2 | kcal/mol | Eqk | Rodgers and Wu, 1971 | gas phase; Heat of isomerization |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.7 ± 0.2 | kcal/mol | Eqk | Rodgers and Wu, 1971 | gas phase; Heat of isomerization |
ΔrH° | -1.8 | kcal/mol | Eqk | Abell, 1966 | gas phase |
By formula: C6H12 + HCl = C6H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -12.91 ± 0.33 | kcal/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.18 ± 0.27 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S.,
Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols,
J. Org. Chem., 1991, 56, 5108-5110. [all data]
Rodgers and Wu, 1971
Rodgers, A.S.; Wu, M.-C.R.,
Thermochemistry of the gas-phase iodine catalyzed isomerization: 2,3-dimethyl-1-butene = 2,3-dimethyl-2-butene,
J. Chem. Thermodyn., 1971, 3, 591-597. [all data]
Scott D.W., 1955
Scott D.W.,
2,3-Dimethyl-2-butene: thermodynamic properties in the solid, liquid and vapor states,
J. Am. Chem. Soc., 1955, 77, 4993-4998. [all data]
Scott, Finke, et al., 1955
Scott, D.W.; Finke, H.L.; McCullough, J.P.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
2,3-Dimethyl-2-butene: Thermodynamic properties in the solid, liquid and vapor states,
J. Am. Chem. Soc., 1955, 77, 4993-4998. [all data]
Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Shomate, C.H.,
Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins,
J. Am. Chem. Soc., 1936, 58, 2505-2508. [all data]
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]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. III. Hydrogenation of some higher olefins,
J. Am. Chem. Soc., 1936, 58, 137-145. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Radyuk, Kabo, et al., 1972
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N.,
Equilibrium and thermodynamics of the isomerization of hexene isomers,
Neftekhimiya, 1972, 12, 679-686. [all data]
Abell, 1966
Abell, P.I.,
Bromine atom catalyzed isomerization of terminal olefins,
J. Am. Chem. Soc., 1966, 88, 1346-1348. [all data]
Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J.,
Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions,
J. Am. Chem. Soc., 1980, 102, 3329-3334. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy 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 ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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