1,3-Butadiene, 2,3-dimethyl-
- Formula: C6H10
- Molecular weight: 82.1436
- 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
The 3d structure may be viewed using Java or Javascript. - 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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Reaction thermochemistry data
Go To: Top, 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
B - John E. Bartmess
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Individual Reactions
By formula: 2H2 + C6H10 = C6H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -231.4 ± 3.0 | kJ/mol | Chyd | Molnar, Rachford, et al., 1984 | liquid phase; solvent: Dioxane; ALS |
ΔrH° | -227.0 ± 2.8 | kJ/mol | Chyd | Molnar, Rachford, et al., 1984 | liquid phase; solvent: Hexane; ALS |
ΔrH° | -223.4 ± 0.63 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1937 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -225.4 ± 0.63 kJ/mol; At 355 °K; ALS |
C6H9- + =
By formula: C6H9- + H+ = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1624. ± 13. | kJ/mol | G+TS | Clifford, Wenthold, et al., 1998 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1590. ± 13. | kJ/mol | IMRB | Clifford, Wenthold, et al., 1998 | gas phase; B |
+
= C12H10N4
By formula: C6H10 + C6N4 = C12H10N4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -165.6 ± 1.8 | kJ/mol | Cm | Rogers, 1972 | liquid phase; ALS |
C12H10N4 = +
By formula: C12H10N4 = C6H10 + C6N4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 165.6 ± 1.8 | kJ/mol | Cm | Rogers, 1972 | solid phase; ALS |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, References, Notes
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) | 835.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 807.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.66 ± 0.05 | EI | Wolkoff, Holmes, et al., 1980 | LLK |
8.62 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
8.66 | EI | Lossing and Traeger, 1975 | LLK |
8.62 | PE | Beez, Bieri, et al., 1973 | LLK |
8.54 ± 0.04 | EI | Bock and Seidl, 1968 | RDSH |
8.709 | S | Price and Walsh, 1940 | RDSH |
8.71 | PE | Werstiuk, Clark, et al., 1990 | Vertical value; LL |
8.71 | PE | Masclet, Mouvier, et al., 1981 | Vertical value; LLK |
8.72 | PE | Worley, Webb, et al., 1979 | Vertical value; LLK |
8.76 | PE | Sustmann and Schubert, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H7+ | 10.22 ± 0.05 | CH3 | EI | Wolkoff, Holmes, et al., 1980 | LLK |
C5H7+ | 8.66 | CH3 | EI | Lossing and Traeger, 1975, 2 | LLK |
C5H7+ | 10.22 | CH3 | EI | Lossing and Traeger, 1975 | LLK |
De-protonation reactions
C6H9- + =
By formula: C6H9- + H+ = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1624. ± 13. | kJ/mol | G+TS | Clifford, Wenthold, et al., 1998 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1590. ± 13. | kJ/mol | IMRB | Clifford, Wenthold, et al., 1998 | gas phase; B |
References
Go To: Top, 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.
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]
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 π-orbitals and non-bonded pseudo-π 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 π-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, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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