Cubane

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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

Quantity Value Units Method Reference Comment
Δfgas  CcbKybett, Carroll, et al., 1966uncertain value: 622.2 ± 4.2 kJ/mol; ALS
Δfgas597.1 ± 5.0kJ/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.

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- + Hydrogen cation = Cubane

By formula: C8H7- + H+ = C8H8

Quantity Value Units Method Reference Comment
Δr1688. ± 13.kJ/molG+TSHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3
Quantity Value Units Method Reference Comment
Δr1659. ± 13.kJ/molIMRBHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3

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)

Quantity Value Units Method Reference Comment
IE (evaluated)8.6 ± 0.1eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)859.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity833.6kJ/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
Δr1688. ± 13.kJ/molG+TSHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3; B
Quantity Value Units Method Reference Comment
Δr1659. ± 13.kJ/molIMRBHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3; B

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]

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

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