2-Butene, 2,3-dimethyl-

• Formula: C₆H₁₂
• Molecular weight: 84.1595
• IUPAC Standard InChI: InChI=1S/C6H12/c1-5(2)6(3)4/h1-4H3 Copy

  
• IUPAC Standard InChIKey: WGLLSSPDPJPLOR-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Constant pressure heat capacity of liquid

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

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 + C₆H₁₂ = C₆H₁₄

=

By formula: C₆H₁₂ = C₆H₁₂

=

By formula: C₆H₁₂ = C₆H₁₂

 +  =

By formula: C₆H₁₂ + HCl = C₆H₁₃Cl

=

By formula: C₆H₁₂ = C₆H₁₂

References

Go To: Top, Condensed phase thermochemistry data, Phase change 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]

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]

Scott, Finke, et al., 1955, 2
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. [all data]

Waddington, 1951
Waddington, G., Personal Commun., U. S. Bur. Mines, Bartlesville, OK, 1951. [all data]

Parks, Todd, et al., 1936, 2
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. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Reid, 1972
Reid, Robert C., Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00, AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637 . [all data]

Camin and Rossini, 1956
Camin, D.L.; Rossini, F.D., Physical properties of the 17 isomeric hexenes of the API research series, J. Phys. Chem., 1956, 60, 1446. [all data]

Camin and Rossini, 1956, 2
Camin, David L.; Rossini, Frederick D., Physical Properties of the 17 Isomeric Hexenes.of the API Research Series, J. Phys. Chem., 1956, 60, 10, 1446-1451, https://doi.org/10.1021/j150544a029 . [all data]

Uusi-Kyyny, Pokki, et al., 2004
Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Kim, Younghun; Aittamaa, Juhani, Isobaric Vapor Liquid Equilibrium for 2,3-Dimethyl-2-butene + Methanol, + Ethanol, + 2-Propanol, or + 2-Butanol at Atmospheric Pressure, J. Chem. Eng. Data, 2004, 49, 2, 251-255, https://doi.org/10.1021/je034106w . [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]

Bevan, Malkin, et al., 1955
Bevan, T.H.; Malkin, T.; Smith, D.B.; Davey, W.; Gwilt, J.R.; Cooper, W.; Kertes, S.; Roberts, J.J.; Ross, W.C.J.; Wilson, Walter; Cummings, G.A.McD.; McLaughlin, E., Notes, J. Chem. Soc., 1955, 1383, https://doi.org/10.1039/jr9550001383 . [all data]

Fried, Baghdoyan, et al., 1971
Fried, Vojtech.; Baghdoyan, Armen.; Malik, Jana., Vapor pressures and densities of 2,3-dimethyl-2-butene and 3,3-dimethyl-1-butene, J. Chem. Eng. Data, 1971, 16, 1, 96-97, https://doi.org/10.1021/je60048a009 . [all data]

Baghdoyan, Malik, et al., 1971
Baghdoyan, A.; Malik, J.; Fried, V., Vapor Pressures and Densities of 2,3-Dimethyl-2-butene and 3,3-Dimethyl-1-butene, J. Chem. Eng. Data, 1971, 16, 1, 96-97, https://doi.org/10.1021/je60048a009 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

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]

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

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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