1-Butene, 3,3-dimethyl-

• Formula: C₆H₁₂
• Molecular weight: 84.1595
• IUPAC Standard InChI: InChI=1S/C6H12/c1-5-6(2,3)4/h5H,1H2,2-4H3 Copy

  
• IUPAC Standard InChIKey: PKXHXOTZMFCXSH-UHFFFAOYSA-N Copy
• CAS Registry Number: 558-37-2
• 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: tert-Butylethene; tert-Butylethylene; tert-Hexene; Neohexene; Trimethylvinylmethane; 2,2-Dimethyl-3-butene; 3,3-Dimethyl-1-butene; 3,3-Dimethylbutene; (CH3)3CCH=CH2; 3,3-Dimethylbut-1-ene; NSC 74119
• 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
  • Phase change data
  • Reaction thermochemistry data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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: Glushko Thermocenter, Russian Academy of Sciences, Moscow

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: 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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

C₆H₁₁^- +  =

By formula: C₆H₁₁^- + H⁺ = C₆H₁₂

=

By formula: C₆H₁₂ = C₆H₁₂

=  + 

By formula: C₆H₁₄ = H₂ + C₆H₁₂

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Kennedy W.D., 1938
Kennedy W.D., Thermal data on organic compounds. XVIII. The heat capacity and entropy of t-butylethylene, J. Am. Chem. Soc., 1938, 60, 1507-1509. [all data]

Kennedy, Shomate, et al., 1938
Kennedy, Wm.D.; Shomate, C.H.; Parks, G.P., Thermal data on organic compounds. XVIII. The heat capacity of and entropy of t-butylethylene, J. Am. Chem. Soc., 1938, 60, 1507-1509. [all data]

Streiff, 1964
Streiff, A.J., , Am. Pet. Inst. Res. Proj. 58B Unpublished, 1964. [all data]

Boord, Henne, et al., 1949
Boord, C.E.; Henne, A.L.; Greenlee, K.W.; Perilstein, W.L.; Derfer, J.M., The Grignard Reagent in hydrocarbon synthesis, Ind. Eng. Chem., 1949, 41, 609. [all data]

Boord, Greenlee, et al., 1946
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L., The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Weight, Am. Pet. Inst. Res. Proj. 45, Eighth Annu. Rep., Ohio State Univ., June 30, 1946. [all data]

Brooks, Howard, et al., 1940
Brooks, D.B.; Howard, F.L.; Crafton, H.C., Physical Properties of Some Purified Aliphatic Hydrocarbons, J. Res. Natl. Bur. Stand. (U. S.), 1940, 24, 33. [all data]

Kennedy, Shomate, et al., 1938, 2
Kennedy, W.D.; Shomate, C.H.; Parks, G.S., Thermal data on organic compounds: xviii the heat capacity and entropy of t-butylethylene, J. Am. Chem. Soc., 1938, 60, 1507-9. [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]

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]

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]

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]

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]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [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]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [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]

Soják, Addová, et al., 2002
Soják, L.; Addová, G.; Kubinec, R.; Kraus, A.; Hu, G., Gas chromatographic-mass spectrometric characterization of all acyclic C₅-C₇ alkenes from fluid catalytic cracked gasoline using polydimethylsiloxane and squalane stationary phases, J. Chromatogr. A, 2002, 947, 1, 103-117, https://doi.org/10.1016/S0021-9673(01)01564-3 . [all data]

Hilal, Carreira, et al., 1994
Hilal, S.H.; Carreira, L.A.; Karickhoff, S.W.; Melton, C.M., Estimation of Gas-Liquid Chromatographic Retention Times from Molecular Structure, J. Chromatogr. A, 1994, 662, 2, 269-280, https://doi.org/10.1016/0021-9673(94)80515-6 . [all data]

Lubeck and Sutton, 1984
Lubeck, A.J.; Sutton, D.L., Kovats Retention Indices of Selected Olefins on Bonded Phase Fused Silica Capillaries, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1984, 7, 9, 542-544, https://doi.org/10.1002/jhrc.1240070913 . [all data]

Chrétien and Dubois, 1977
Chrétien, J.R.; Dubois, J.E., Topological analysis of gas-liquid chromatographic behavior of alkenes, Anal. Chem., 1977, 49, 6, 747-756, https://doi.org/10.1021/ac50014a021 . [all data]

Chretien and Dubois, 1976
Chretien, J.R.; Dubois, J.-E., New Perspectives in the Prediction of Kovats Indices, J. Chromatogr., 1976, 126, 171-189, https://doi.org/10.1016/S0021-9673(01)84071-1 . [all data]

Rijks and Cramers, 1974
Rijks, J.A.; Cramers, C.A., High precision capillary gas chromatography of hydrocarbons, Chromatographia, 1974, 7, 3, 99-106, https://doi.org/10.1007/BF02269819 . [all data]

Matukuma, 1969
Matukuma, A., Retention indices of alkanes through C₁₀ and alkenes through C₈ and relation between boiling points and retention data, Gas Chromatogr., Int. Symp. Anal. Instrum. Div Instrum Soc. Amer., 1969, 7, 55-75. [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Zulaïca and Guiochon, 1966
Zulaïca, J.; Guiochon, G., Analyse des hauts polymères par chromatographie en phase gazeuse de leurs produits de pyrolyse. II. Application à quelques hydrocarbures macromoléculaires purs, Bull. Soc. Chim. Fr., 1966, 4, 1351-1363. [all data]

Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory, Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]

Hoekman, 1993
Hoekman, S.K., Improved gas chromatography procedure for speciated hydrocarbon measurements of vehicle emissions, J. Chromatogr., 1993, 639, 2, 239-253, https://doi.org/10.1016/0021-9673(93)80260-F . [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

Sojak, Addova, et al., 2000
Sojak, L.; Addova, G.; Kubinec, R.; Ruman, J.; Hu, G., GC-MS characterization of all acyclic C5-C7 alkenes from FCC gasoline using squalane stationary phase, Petroleum and Coal, 2000, 42, 3-4, 188-194. [all data]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und Struktur Chemischer Verbindungen. II. Methylverzweigungen und Doppelbindungen in Offenkettigen Kohlenwasserstoffen, J. Chromatogr., 1966, 23, 1-17, https://doi.org/10.1016/S0021-9673(01)98652-2 . [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]

Supelco, 2012
Supelco, CatalogNo. 24160-U, Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]

Ramnas, Ostermark, et al., 1994
Ramnas, O.; Ostermark, U.; Peterson, G., Characterization of sixty alkenes in a cat-cracked gasoline naphtha by gas chromatography, Chromatographia, 1994, 38, 3/4, 222-226, https://doi.org/10.1007/BF02290340 . [all data]

Chen and Feng, 2007
Chen, Y.; Feng, C., QSPR study on gas chromatography retention index of some organic pollutants, Comput. Appl. Chem. (China), 2007, 24, 10, 1404-1408. [all data]

Junkes, Castanho, et al., 2003
Junkes, B.S.; Castanho, R.D.M.; Amboni, C.; Yunes, R.A.; Heinzen, V.E.F., Semiempirical Topological Index: A Novel Molecular Descriptor for Quantitative Structure-Retention Relationship Studies, Internet Electronic Journal of Molecular Design, 2003, 2, 1, 33-49. [all data]

Perkin Elmer Instruments, 2002
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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  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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