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 Copy

  
• IUPAC Standard InChIKey: SDJHPPZKZZWAKF-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₉^- +  =

By formula: C₆H₉^- + H⁺ = C₆H₁₀

References

Go To: Top, 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.

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]

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]

Notes

Go To: Top, 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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