Cubane

• Formula: C₈H₈
• Molecular weight: 104.1491
• IUPAC Standard InChI: InChI=1S/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H Copy

  
• IUPAC Standard InChIKey: TXWRERCHRDBNLG-UHFFFAOYSA-N Copy
• CAS Registry Number: 277-10-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₈H₈⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₈H₇^- +  =

By formula: C₈H₇^- + H⁺ = C₈H₈

References

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

Kybett, Carroll, et al., 1966
Kybett, B.D.; Carroll, S.; Natalis, P.; Bonnell, D.W.; Margrave, J.L.; Franklin, J.L., Thermodynamic properties of cubane, J. Am. Chem. Soc., 1966, 88, 626. [all data]

Kybett, Carroll, et al., 1966, 2
Kybett, B.D.; Carroll, S.; Natalis, P.; Bonnell, D.W.; Margrave, J.L.; Franklin, J.L., Thermodynamic Properties of Cubane, J. Am. Chem. Soc., 1966, 88, 3, 626-626, https://doi.org/10.1021/ja00955a056 . [all data]

Bashir-Hashemi, Chickos, et al., 2004
Bashir-Hashemi, A.; Chickos, James S.; Hanshaw, William; Zhao, Hui; Farivar, Behzad S.; Liebman, Joel F., The enthalpy of sublimation of cubane, Thermochimica Acta, 2004, 424, 1-2, 91-97, https://doi.org/10.1016/j.tca.2004.05.022 . [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]

Lifshitz and Eaton, 1983
Lifshitz, C.; Eaton, P.E., Time-dependent mass spectra and breakdown graphs. III. The cubane cation complete or partial instability, Int. J. Mass Spectrom. Ion Phys., 1983, 49, 337. [all data]

Gassman and Yamaguchi, 1979
Gassman, P.G.; Yamaguchi, R., Electrochemical oxidation of strained hydrocarbons, J. Am. Chem. Soc., 1979, 101, 1308. [all data]

Bischof, Eaton, et al., 1978
Bischof, P.; Eaton, P.E.; Gleiter, R.; Heilbronner, E.; Jones, T.B.; Musso, H.; Schmelzer, A.; Stober, R., 44. The electronic structure of cubane (C₈H₈) as revealed by photoelectron spectroscopy, Helv. Chim. Acta, 1978, 61, 547. [all data]

Gross, 1972
Gross, M.L., Ion cyclotron resonance spectrometry. A means of evaluating 'kinetic shifts', Org. Mass Spectrom., 1972, 6, 827. [all data]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., The effect of molecular structure on ionic decomposition. I. An electron impact study of seven C₈H₈ isomers, J. Am. Chem. Soc., 1969, 91, 5940. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Hare, Emrick, et al., 1997
Hare, M.; Emrick, T.; Eaton, P.E.; Kass, S.R., Cubyl Anion Formation and an Experimental Determination of the Acidity and C-H Bond Dissociation Energy of Cubane, J. Am. Chem. Soc., 1997, 119, 1, 237, https://doi.org/10.1021/ja9627858 . [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  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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