Cubane

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase 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

Quantity Value Units Method Reference Comment
Δfgas  CcbKybett, Carroll, et al., 1966uncertain value: 148.7 ± 1.0 kcal/mol; ALS
Δfgas142.7 ± 1.2kcal/molCcbKybett, Carroll, et al., 1966, 2Value recomputed with updated enthalpy of sublimation from Bashir-Hashemi, Chickos, et al., 2004. The value used in the original paper is now deemed unreliable.

Gas phase ion energetics data

Go To: Top, Gas phase 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
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)

Quantity Value Units Method Reference Comment
IE (evaluated)8.6 ± 0.1eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)205.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity199.2kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.6 ± 0.1TRPILifshitz and Eaton, 1983LBLHLM
8.46PEGassman and Yamaguchi, 1979LLK
8.6PEBischof, Eaton, et al., 1978LLK
8.4 ± 0.1EIGross, 1972LLK
8.64 ± 0.10EIFranklin and Carroll, 1969RDSH
8.74PEDewar and Worley, 1969RDSH
8.74 ± 0.15EIKybett, Carroll, et al., 1966RDSH
9.00PEBischof, Eaton, et al., 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+10.01 ± 0.10?EIFranklin and Carroll, 1969RDSH
C4H2+14.33 ± 0.202C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H3+14.96 ± 0.102C2H2+HEIFranklin and Carroll, 1969RDSH
C4H4+12.88 ± 0.152C2H2EIFranklin and Carroll, 1969RDSH
C5H3+13.60 ± 0.10?EIFranklin and Carroll, 1969RDSH
C6H5+10.93 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C6H6+8.8 ± 0.1C2H2TRPILifshitz and Eaton, 1983LBLHLM
C6H6+9.2 ± 0.1?EIGross, 1972LLK
C6H6+9.00 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C8H6+8.92 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C8H7+9.3 ± 0.2HTRPILifshitz and Eaton, 1983LBLHLM
C8H7+8.96 ± 0.10HEIFranklin and Carroll, 1969RDSH

De-protonation reactions

C8H7- + Hydrogen cation = Cubane

By formula: C8H7- + H+ = C8H8

Quantity Value Units Method Reference Comment
Δr403.4 ± 3.1kcal/molG+TSHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3; B
Quantity Value Units Method Reference Comment
Δr396.5 ± 3.0kcal/molIMRBHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3; B

References

Go To: Top, Gas phase 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]

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

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