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1,3-Butadiene, 2,3-dimethyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
117.9273.15Durig J.R., 1979It should be noted that values of S(T) and Cp(T) calculated by Durig et al. [ Durig J.R., 1980, Durig J.R., 1980, 2, Durig J.R., 1981] for alkenes are different from experimental ones and given in TRC Tables [ Thermodynamics Research Center, 1997] by 3-5 J/mol*K. So the accuracy of their data could exceed 2 J/mol*K.
127. ± 2.298.15
127.1300.
159.9400.
188.5500.
212.3600.
232.2700.
249.0800.
263.4900.
275.81000.

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
Deltacliquid-3815.kJ/molCcbHandrick, 1956Kogerman, P. N., 1934; Corresponding «DELTA»fliquid = 24. 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil342. ± 3.KAVGN/AAverage of 13 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus199. ± 8.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Deltavap31.kJ/molVRogers, 1972ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
32.2288.AStephenson and Malanowski, 1987Based on data from 273. - 342. K. See also Bevan, Malkin, et al., 1955.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
273.19 - 341.64.272181315.15-33.416Cummings and McLaughlin, 1955Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

2Hydrogen + 1,3-Butadiene, 2,3-dimethyl- = Butane, 2,3-dimethyl-

By formula: 2H2 + C6H10 = C6H14

Quantity Value Units Method Reference Comment
Deltar-231.4 ± 3.0kJ/molChydMolnar, Rachford, et al., 1984liquid phase; solvent: Dioxane; ALS
Deltar-227.0 ± 2.8kJ/molChydMolnar, Rachford, et al., 1984liquid phase; solvent: Hexane; ALS
Deltar-223.4 ± 0.63kJ/molChydDolliver, Gresham, et al., 1937gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -225.4 ± 0.63 kJ/mol; At 355 °K; ALS

C6H9- + Hydrogen cation = 1,3-Butadiene, 2,3-dimethyl-

By formula: C6H9- + H+ = C6H10

Quantity Value Units Method Reference Comment
Deltar1624. ± 13.kJ/molG+TSClifford, Wenthold, et al., 1998gas phase; B
Quantity Value Units Method Reference Comment
Deltar1590. ± 13.kJ/molIMRBClifford, Wenthold, et al., 1998gas phase; B

1,3-Butadiene, 2,3-dimethyl- + Tetracyanoethylene = C12H10N4

By formula: C6H10 + C6N4 = C12H10N4

Quantity Value Units Method Reference Comment
Deltar-165.6 ± 1.8kJ/molCmRogers, 1972liquid phase; ALS

C12H10N4 = 1,3-Butadiene, 2,3-dimethyl- + Tetracyanoethylene

By formula: C12H10N4 = C6H10 + C6N4

Quantity Value Units Method Reference Comment
Deltar165.6 ± 1.8kJ/molCmRogers, 1972solid phase; ALS

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference
0.021 VN/A

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

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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 C6H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)835.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity807.8kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.66 ± 0.05EIWolkoff, Holmes, et al., 1980LLK
8.62 ± 0.02PEBieri, Burger, et al., 1977LLK
8.66EILossing and Traeger, 1975LLK
8.62PEBeez, Bieri, et al., 1973LLK
8.54 ± 0.04EIBock and Seidl, 1968RDSH
8.709SPrice and Walsh, 1940RDSH
8.71PEWerstiuk, Clark, et al., 1990Vertical value; LL
8.71PEMasclet, Mouvier, et al., 1981Vertical value; LLK
8.72PEWorley, Webb, et al., 1979Vertical value; LLK
8.76PESustmann and Schubert, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H7+10.22 ± 0.05CH3EIWolkoff, Holmes, et al., 1980LLK
C5H7+8.66CH3EILossing and Traeger, 1975, 2LLK
C5H7+10.22CH3EILossing and Traeger, 1975LLK

De-protonation reactions

C6H9- + Hydrogen cation = 1,3-Butadiene, 2,3-dimethyl-

By formula: C6H9- + H+ = C6H10

Quantity Value Units Method Reference Comment
Deltar1624. ± 13.kJ/molG+TSClifford, Wenthold, et al., 1998gas phase; B
Quantity Value Units Method Reference Comment
Deltar1590. ± 13.kJ/molIMRBClifford, Wenthold, et al., 1998gas phase; B

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-4073
NIST MS number 227631

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes

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

Durig J.R., 1979
Durig J.R., Analysis of torsional spectra of molecules with two internal C3v rotors. 16. Infrared and Raman spectra, vibrational assignment, methyl torsional potential function, and gas phase thermodynamic functions of 2,3-dimethylbuta-1,3-diene, J. Phys. Chem., 1979, 83, 2879-2886. [all data]

Durig J.R., 1980
Durig J.R., Spectroscopic and thermodynamic study of conformational properties and torsional potential functions of 1-butene, J. Phys. Chem., 1980, 84, 773-781. [all data]

Durig J.R., 1980, 2
Durig J.R., Torsional spectra of molecules with two internal C3v rotors. 19. Vibrational spectra, torsional potential functions, and conformational and thermodynamic properties of 2-methyl-1-butene, J. Phys. Chem., 1980, 84, 3554-3561. [all data]

Durig J.R., 1981
Durig J.R., Analysis of torsional spectra of molecules with two internal C3v rotors. 20. Vibrational spectra, torsional potential functions, and conformational and thermodynamic properties of 3-methyl-1-butene, J. Phys. Chem., 1981, 85, 426-434. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Handrick, 1956
Handrick, G.R., Report of the study of pure explosive compounds. Part IV. Calculation of heat of combustion of organic compounds from structural features and calculation of power of high explosives, Rpt. C-58247 for the Office of the Chief of Ordnance, contract DA-19-020-ORD-47 by the Arthur D. Little, Inc., Cambridge, MA, 1956, 467-573. [all data]

Rogers, 1972
Rogers, F.E., Thermochemistry of the Diels-Alder reactions. II. Heat of addition of several dienes to tetracyanoethylene, J. Phys. Chem., 1972, 76, 106-109. [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]

Cummings and McLaughlin, 1955
Cummings, G.A.McD.; McLaughlin, E., Vapour Pressures of Some Unsaturated Hydrocarbons Containing Six Carbon Atoms, J. Chem. Soc., 1955, 1391-1392. [all data]

Molnar, Rachford, et al., 1984
Molnar, A.; Rachford, R.; Smith, G.V.; Liu, R., Heats of hydrogenation by a simple and rapid flow calorimetric method, Appl. Catal., 1984, 9, 219-223. [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]

Clifford, Wenthold, et al., 1998
Clifford, E.P.; Wenthold, P.G.; Lineberger, W.C.; Ellison, G.B.; Wang, C.X.; Grabowski, J.J.; Vila, F.; Jordan, Properties of Tetramethyleneethane (TME) as Revealed by Ion Chemistry and Ion Photoelectron Spectroscopy, J. Chem. Soc. Perkin Trans., 1998, 2, 5, 1015, https://doi.org/10.1039/a707322d . [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]

Wolkoff, Holmes, et al., 1980
Wolkoff, P.; Holmes, J.L.; Lossing, F.P., On the formation of cyclopentenium cations from all C6H10+ molecular ion structures, Can. J. Chem., 1980, 58, 251. [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]

Beez, Bieri, et al., 1973
Beez, M.; Bieri, G.; Bock, H.; Heilbronner, E., The ionization potentials of butadiene, hexatriene, andtheir methyl derivatives: evidence for through space interaction between double bond «pi»-orbitals and non-bonded pseudo-«pi» orbitals of methyl groups?, Helv. Chim. Acta, 1973, 56, 1028. [all data]

Bock and Seidl, 1968
Bock, H.; Seidl, H., 'd-Orbital effects' in silicon- substituted «pi»-electron systems. XI. Syntheses and properties of the isomeric bis(trimethylsilyl)-1,3-butadienes, J. Am. Chem. Soc., 1968, 90, 5694. [all data]

Price and Walsh, 1940
Price, W.C.; Walsh, A.D., The absorption spectra of conjugated dienes in the vacuum ultra-violet (1), Proc. Roy. Soc. (London), 1940, A174, 220. [all data]

Werstiuk, Clark, et al., 1990
Werstiuk, N.H.; Clark, K.B.; Leigh, W.J., Conformational analysis and structure elucidation of 2,3-dimethyl and 2,4-dimethyl-2,4-hexadienes by AM1 and He(I) ultraviolet photoelectron spectroscopy, Can. J. Chem., 1990, 68, 2078. [all data]

Masclet, Mouvier, et al., 1981
Masclet, P.; Mouvier, G.; Bocquet, J.F., Effets electroniques et effets steriques dus a la substitution alcoyle dans les dienes conjugues, J. Chim. Phys., 1981, 78, 99. [all data]

Worley, Webb, et al., 1979
Worley, S.D.; Webb, T.R.; Gibson, D.H.; Ong, T.-S., On the electronic structures of cyclobutadiene trimethylenemethane, J. Organomet. Chem., 1979, 168, 16. [all data]

Sustmann and Schubert, 1972
Sustmann, R.; Schubert, R., Photoelektronenspektroskopische bestimmung von substituenten-effekten. I. Subtituierte butadiene, Tetrahedron Lett., 1972, 27, 2739. [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, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References