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

Formula: C₆H₁₀
Molecular weight: 82.1436
IUPAC Standard InChI: InChI=1S/C6H10/c1-5(2)6(3)4/h1,3H2,2,4H3
IUPAC Standard InChIKey: SDJHPPZKZZWAKF-UHFFFAOYSA-N
CAS Registry Number: 513-81-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Biisopropenyl; Diisopropenyl; 2,3-Dimethyl-1,3-butadiene; 2,3-Dimethylbuta-1,3-diene; 2,3-Dimethylbutadiene; CH2=C(CH3)C(CH3)=CH2; 2,3-Dimethylenebutane
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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
28.18	273.15	Durig J.R., 1979	It 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/molK. So the accuracy of their data could exceed 2 J/molK.
30.2 ± 0.5	298.15
30.38	300.
38.22	400.
45.05	500.
50.74	600.
55.50	700.
59.51	800.
62.95	900.
65.92	1000.

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-911.7	kcal/mol	Ccb	Handrick, 1956	Kogerman, P. N., 1934; Corresponding Δ_fHº_liquid = 5.8 kcal/mol (simple calculation by NIST; no Washburn corrections)

Reaction thermochemistry data

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

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Individual Reactions

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

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-55.31 ± 0.72	kcal/mol	Chyd	Molnar, Rachford, et al., 1984	liquid phase; solvent: Dioxane; ALS
Δ_rH°	-54.26 ± 0.67	kcal/mol	Chyd	Molnar, Rachford, et al., 1984	liquid phase; solvent: Hexane; ALS
Δ_rH°	-53.39 ± 0.15	kcal/mol	Chyd	Dolliver, Gresham, et al., 1937	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -53.87 ± 0.15 kcal/mol; At 355 °K; ALS

C₆H₉^- + = 1,3-Butadiene, 2,3-dimethyl-

By formula: C₆H₉^- + H⁺ = C₆H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	388.1 ± 3.1	kcal/mol	G+TS	Clifford, Wenthold, et al., 1998	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	380.0 ± 3.0	kcal/mol	IMRB	Clifford, Wenthold, et al., 1998	gas phase; B

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

By formula: C₆H₁₀ + C₆N₄ = C₁₂H₁₀N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-39.57 ± 0.44	kcal/mol	Cm	Rogers, 1972	liquid phase; ALS

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

By formula: C₁₂H₁₀N₄ = C₆H₁₀ + C₆N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	39.57 ± 0.44	kcal/mol	Cm	Rogers, 1972	solid phase; ALS

References

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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]

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]

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]

Notes

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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