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:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 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

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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

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

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

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

View reactions leading to C₆H₁₂⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [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]

Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C., Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations, J. Am. Chem. Soc., 1975, 97, 1579. [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]

Frost and Sandhu, 1971
Frost, D.C.; Sandhu, J.S., Ionization potentials of ethylene and some methyl-substituted ethylenes as determined by photoelectron spectroscopy, Indian J. Chem., 1971, 9, 1105. [all data]

Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C., The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proc. Roy. Soc. (London), 1960, A258, 459. [all data]

Kovac, Mohraz, et al., 1980
Kovac, B.; Mohraz, M.; Heilbronner, E.; Boekelheide, V.; Hopf, H., Photoelectron spectra of the cyclophanes, J. Am. Chem. Soc., 1980, 102, 4314. [all data]

McAlduff and Houk, 1977
McAlduff, E.J.; Houk, K.N., Photoelectron spectra of substituted oxiranes and thiiranes. Substituent effects on ionization potentials involving σ orbitals, Can. J. Chem., 1977, 55, 318. [all data]

Mollere, Houk, et al., 1976
Mollere, P.D.; Houk, K.N.; Bomse, D.S.; Morton, T.H., Photoelectron spectra of sterically congested alkenes and dienes, J. Am. Chem. Soc., 1976, 98, 4732. [all data]

Fuss and Bock, 1974
Fuss, W.; Bock, H., Photoelectron spectra and molecular properties. XXXVI. (H₃C)₃B, (H₃C)₂BF, (H₃C)₂BN(CH₃)₂, and (H₃C)₂CC(CH₃)₂: The use of ionization potentials in assigning UV spectra, J. Chem. Phys., 1974, 61, 1613. [all data]

Lossing and Traeger, 1975, 2
Lossing, F.P.; Traeger, J.C., Free radicals by mass spectrometry XLVI. Heats of formation of C₅H₇ and C₅H₉ radicals and cations., J. Am. Chem. Soc., 1975, 19, 9. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  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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