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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
Deltafgas  CcbKybett, Carroll, et al., 1966uncertain value: 148.7 ± 1.0 kcal/mol; ALS
Deltafgas142.7 ± 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.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafsolid129.5 ± 0.8kcal/molCcbKybett, Carroll, et al., 1966 
Quantity Value Units Method Reference Comment
Deltacsolid-1155.18kcal/molCcbKybett, Carroll, et al., 1966Corresponding «DELTA»fsolid = 129.51 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change 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:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltavap10.7 ± 0.2kcal/molCGCBashir-Hashemi, Chickos, et al., 2004AC
Quantity Value Units Method Reference Comment
Deltasub13.2 ± 0.48kcal/molAC+CGCBashir-Hashemi, Chickos, et al., 2004AC
Deltasub  MEKybett, Carroll, et al., 1966, 2uncertain value: 19.2 ± 0.38 kcal/mol; in Ref. Diky, Frenkel, et al., 2003 the authors state that the value of 80.3 kJ/mole from Kybett, Carroll, et al., 1966, 2 pertains to the average temperature and not to 298 K. The authors give a value of 79.1±1.7 for the 298 K value; AC

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
19.2 ± 0.4239.VKybett, Carroll, et al., 1966ALS

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
2.1404.9ACWhite, Wasylishen, et al., 1992AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
3.604394.White, Wasylishen, et al., 1992, 2CAL
5.136404.9

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.420395.04crystaline, IIcrystaline, IWhite, Wasylishen, et al., 1992DH
2.079404.9crystaline, IliquidWhite, Wasylishen, et al., 1992DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
3.674395.04crystaline, IIcrystaline, IWhite, Wasylishen, et al., 1992DH
5.43404.9crystaline, IliquidWhite, Wasylishen, et al., 1992DH

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
Deltar403.4 ± 3.1kcal/molG+TSHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3
Quantity Value Units Method Reference Comment
Deltar396.5 ± 3.0kcal/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)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
Deltar403.4 ± 3.1kcal/molG+TSHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3; B
Quantity Value Units Method Reference Comment
Deltar396.5 ± 3.0kcal/molIMRBHare, Emrick, et al., 1997gas phase; Comparable to ammonia; D exchange with ND3; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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]

Diky, Frenkel, et al., 2003
Diky, Vladimir V.; Frenkel, Michael; Karpushenkava, Larisa S., Thermodynamics of sublimation of cubane: natural anomaly or experimental error?, Thermochimica Acta, 2003, 408, 1-2, 115-121, https://doi.org/10.1016/S0040-6031(03)00318-6 . [all data]

White, Wasylishen, et al., 1992
White, M.A.; Wasylishen, R.E.; Eaton, P.E.; Xiong, Y.; Pramod, K.; Nodari, N., Orientational disorder in solid cubane: a thermodynamic and 13C NMR study, J. Phys. Chem., 1992, 96(1), 421-425. [all data]

White, Wasylishen, et al., 1992, 2
White, M.A.; Wasylishen, R.E.; Eaton, P.E.; Xiong, Y.; Pramod, K.; Nodari, N., Orientational disorder in solid cubane: a thermodynamic and carbon-13 NMR study, J. Phys. Chem., 1992, 96, 1, 421, https://doi.org/10.1021/j100180a078 . [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References