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
  The 3d structure may be viewed using Java or Javascript.
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• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, Reaction thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 by: 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

C₈H₇^- +  =

By formula: C₈H₇^- + H⁺ = C₈H₈

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

Go To: Top, Gas phase thermochemistry data, 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.

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]

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]

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]

Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

• 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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